Gabriel Simons

Director of Communications (Jake's route and Gabriel's route after being promoted at the final chapter)
 Branch Manager (Colin's route)

## Physical description

### Eye color

Blue

**Gabriel Simons** is a manager within Carter Corp. a serial romanticist and the son of both Steven Simons and Holly Simons serving as the main love interest within his own story route. In other character story routes, he serves as a supporting character.

## Appearance

Gabriel has short pale blond hair in a wavy style with single fringes in each side and blue eyes. Both his pale blond hair and his blue eyes as well as his charismatic personality are taken from his father, Steven and his hourglass shape of his face, his pecs and his negative traits of his personality are taken from his mother Holly.

He wore four outfits in the game and he is commonly seen wearing a dark purple corporate business suit with a matching dark purple formal vest and a white long sleeved button up-shirt along with a purple tie on the collar, dark purple pants and black shoes. He also wears a gold ring on his right middle finger.

His other corporate attire is black but without tie. On one secret scene shows him without his corporate jacket.

His third outfit is his semi-casual attire, a gray formal suit jacket with a short sleeved v-neck shirt, dark gray jeans and black leather shoes.

His fourth outfit which was seen at the beginning of the second season, Gabriel now wears a long sleeve plunging v-neck shirt which shows off his clavicles and the sleeves just reach his elbows, brown jeans and black leather shoes. He also wears a brown watch on his left wrist.

* When he begins to spend a romantic night with the player at the hotel, he was shirtless to show off his well-toned physique and wears only a white and purple stripped trouser. His shirtless portrait has him wearing black and purple stripped trousers. Later in Season 2 during the second chapter, Gabriel is seen in a black boxers where he tries to make love to the player on his office.

## Personality

Gabriel is best described as being a serious but charismatic person and is impressed with the players' work as her manager. In later chapters Gabriel is shown to have a more playful and caring side when he is dating the player. Like Matt, he is a brave and confident individual especially when he protects someone.

This is seen in Chapter 10 when he defends himself and the player after Matt became jealous and angry after seeing Gabriel with her and how Gabriel had broken her heart, eventually leading to a fistfight. The most prominent trait of his personality is his charm, partially due to his handsome looks and his well-toned physique. Unlike the other athletic and handsome men the player is involved with Gabriel often displays his affection for her via simple romantic acts and this is one of the main reasons she is attracted to him. At the second season, he maintains his personality from before and always taking the player for dates. He hates being questioned about his past life, his jealousy to Matt became more prominent than before after learning that she invites him at Atlantic City for Lisa's birthday and always changing the subject which is the same as how Matt did to the player in his main story route. These personal questions leads Gabriel to break the player up without a reason at the end of the chapter, stating that their relationship is over and never answer her questions after she explained to him when Matt takes her out and drinking with their friends. Although he does this in order to protect the player despite his actions. He also disapproves of Matt for inviting the player to Daryl's party because of the accident he pulled off in the illegal car race. Gabriel is also shown to have money problems when one of his credit cards were declined after he spent a fortune to hire a private detective to find his father Steven, and the player noticed he's taking a red tape.

In Chapter 6, and like Matt, Adam and Colin, Gabriel also shows his rebellious side after he claims that his father is dead in the first season, but he's alive in the second season and his relationship with his father Steven is completely strained because of his actions and his knack of gambling as well as for breaking his mother's heart when they got separated. This also shows at the end of the same chapter where Gabriel calls his father by his first name Steven rather than saying "dad". Gabriel also respects his mother Holly when he defends the player from her. Although, Steven knows that Holly had already brainwashed him to no longer trust him following their separation. In Chapter 9, this shows Gabriel's depression over his family's problems including his mother Holly is suffering from cancer. Despite his protection to the player when he rescues her from his father Steven, Gabriel has his own faults when he violently pushes his father away to stop him from hurting the player causing the latter to get panicked and slipped into the ground, injuring his head in a process. At the final chapter of the story, he reveals another of his secrets that he keeps the alcoholic bottles under his office which is illegal and showing his unawareness that the player had already taken resignation from the company after Cassidy had instigated a catfight and being mistreated by Mark thinking she was behind the catfight. His intelligence is also displayed when he succeeds in apprehending his own father by entrapment operation with the help from Jenny Blake who serves as his right-hand woman (as the player mistook her being a love rival to him). Although he expresses his disappointment in the bad ending where he fails to apprehend his father Steven who later escape from the authorities, leading him to break the player for his failures.

In Matt's story, however, Gabriel is revealed to be strict such as when he asks Matt to come to his office due to them both having expressed an attraction towards the player during Daryl's party. Consequently he separates Matt and the player by moving their cubicles to different places so they would not share an office space due to all their arguing. This also happens in the final chapter when the tension between the two leads to Gabriel instructing the player to choose either himself or Matt. But in the second season in Chapter 8, Gabriel angrily tries to reprimand the player about their relationship with Matt due to Cassidy's meddling until the player retaliates by angrily complaining to him about Cassidy's horrible mistreatment to her much to his horrible shock and informs her to investigate this matter but he retains his motives to reprimand them once he found out about their relationship between them, Gabriel was okay with it at first as long as it didn't effect their work, but unfortunately it did which caused him to be disappointed in them. In Chapter 10, Gabriel had caught them on the spot which brings them to his office and informs them regarding about his promotion to his superiors, particularly it will be done by both Ryan and Mark but Matt insults him because he didn't care much about his promotion, resulting in him being suspended by him for trash talking and informs the player to calm him down but his plan failed when Matt decided to leave the building. Despite his more stern side, Gabriel clearly has an interest in the player as he once asked her out fir drinks, and also displays curiosity in her and her involvement with Matt, such as when he takes her to lunch and inquires more about their relationship.

In Ryan's story during Chapter 9, it was revealed that both Gabriel and Mark Leviels were engaging in romantic affairs with Cassidy Sparke as she was the main reason for being used by Alicia Boone as her pass code was needed for entering the HR archives and how she was recruited in the company itself and was found by Ryan Carter, the player and Colin Spencer. In the third and final season which is three years after both seasons, he displays both his sinister side and abusive of power when he decided to assist his former colleague and Leopold Williamson's best friend, Laurens Van Daele in his mayoral elections by making a mayoral campaign and trying to take down their boss Ryan Carter in order to get a higher position.

In Colin's story according to the player, Gabriel is a nice boss as a Communications Manager. But on the second season, she displays her dislike of him for being promoted as a Branch Manager (replacing Mark due to him working on the same position in some branches at Carter Corp) and giving Alicia some new projects consisting of hundreds of documents.

In Daryl's story, Gabriel maintains his stern side and is somewhat strict when he pressures the player during work, and the player had always thought of him as selfish and self-righteous, that was until when Cassidy made a meeting with him and Mark to get the player fired from her absences at the meeting room, and Gabriel stuck up for the player and defended her from Cassidy's remarks and insults in front of Mark to save her from being fired sine she was on his team. However in Chapter 8, Gabriel reprimands the player for her many absences and her negligence to her work due to her being AWOL but he is unaware that the player and her brother Jason whom she tried to saved are on pursuit by the mafia group led by Giorgio Maccini and she always came to the aid from Matt's twin brother, Daryl Ortega.

In Jake's story, it was revealed that he is friends with Ashton Darrow and his now ex-girlfriend the player was his rival during their Harvard days. Despite of their respective careers however, Gabriel is knowledgeable about their former relationship and became friendly to the player when she asks him about relationships and the two have a very friendly relationship that involves a lot of teasing, and he often texts her to see how she's doing during her trip in Russia. But in Chapter 4, it was Gabriel who speaks to Ashton about his problems after renewing his romantic attraction to the player following their break up right from the beginning only for the player to rebuff him saying that she was already interested in Jake instead of Ashton. In chapter 5, he appears at the player's hotel and comforts her when she's upset and she even gives him a kiss on the cheek. But when she opens her hotel door she finds Jake who sees the two of them together and he presumes that the two of them had gotten together and got jealous. Gabriel had found the whole thing amusing and defended himself saying that the player is too much of a challenge for him. The player had rebuffed Jake telling him that it's wrong of him to judge her so hastily which made him feel bad and made Gabriel laugh. Gabriel then gave the player a kiss on her cheek and said that love triangles are not his thing, and that he'd rather be center stage. The two of them giggled when Jake had stormed off and Gabriel had teased her that is is very obvious that she and Jake have feelings for each other. In Chapter 9, despite his flirtatious acts on many women he meets, Gabriel was very concerned towards his friends who are dear to him and always consoled the player about Ashton's well being after he was shot. He also accepts the player's decision after she opens up about her feelings with Jake when he openly asked her between both Ashton and Jake during the chess game.

## Season 1

Gabriel Simons is the son of Steven Simons and Holly Simons. According to him, both of his parents were separated after Steven wasted his entire fortune for his knack of gambling and breaking Holly's heart when they get separated. Gabriel's family is now broken as both him and Steven had growing distant since and the only thing Steven left behind on his family was the silver ring and Gabriel wears it in memory of him. At this point during the time Holly raised him solely, Gabriel learns to hate his father Steven. Prior to their separation, Steven teaches Gabriel to play a game of chess which he successfully did and he accomplish this by winning any chess competition a few times. Gabriel is revealed to study Harvard in college alongside Ashton Darrow and the player. During his college studies, this is where Gabriel learns of his father Steven's knack of gambling caused him to have many debts and leaving his family behind for protection. Gabriel decided to look after his mother Holly. After graduating from Harvard, Gabriel was hired at Carter Corp in Manhattan, New York as the manager of the communications department whose true ambition is to get himself promoted as the Director of Communications. All the while after discovering his sexuality at early age, Gabriel earns the reputation as a serial romanticist where he easily developing romantic feelings towards the women he had met and he cannot control of it which happens to be his weakness and always had conquest without taking to commit these relationships that he had currently made.

Several years later, Gabriel currently works as the manager of Carter Corp. serving as the player's boss who is a new employee. He is also a serial romanticist who became interested in the player after getting rejected by many women he had past relationships with at hands of his colleague and HR manager Cassidy Sparke. Despite meeting new colleagues and higher officials, she begins to have conflicts with Matt Ortega and her boss Gabriel when it comes to romantic relationships. He even mentioning about his past to the father and claiming that his father Steven is dead when he keeps the silver ring on his finger.

Gabriel has an interest in the player from the start, and was worried about her well being on her first day of work after finding out that she was mugged and her belongings were stolen. He dances with the player at Starlite later and calls her delicious. He then later has a lunch break with her and was aroused to see her eat cake at Chez Felipe. When he has to go on a business trip with Cassidy Sparke, this makes the player jealous and she went to Starlite to take her mind off things only to send an inappropriate text of her and a random man dancing to Gabriel and told him that she was having fun too.

When Gabriel returned from his business trip, he was furious at the player and called the file she and Matt worked on junk and yelled at her that they were not friends. Later on, he sent her a text asking if they can meet up and he apologizes to her for yelling and then begins to tell her about his father. The 2 of them share their first kiss that night and start a relationship afterwards.

In Chapter 10, both Gabriel and Matt had a fistfight due to the player's expense and because of their liking to her. Matt was extremely jealous upon learning of their relationship and wanted avenge the player after Gabriel had upset her.

In the final chapter of the story, the player learns that Cassidy and Gabriel made out in the parking garage after an anonymous sender sent her picture of them which leads the player to break up with him. Gabriel soon apologizes for Cassidy's actions and explains that they had a one night stand before he met the player and wanted the player to give him another chance, the player agrees and they reconciled their relationship after Gabriel surprised her with a date on a rooftop.

The bad ending takes place after Gabriel refuses to acknowledge his past relationship with Cassidy stating that it's none of her business and the player furiously leaves Gabriel during the break up stating that Matt was telling the truth about him and decides to start a relationship with Matt.

## Season 2

In the beginning of Season 2, he was shown to be upset after having put work before the player. He also upset the player after denying her and Matt's request to take the week off to celebrate Lisa's birthday in Atlantic City prior to the season 2 events. He claimed that it was because he couldn't afford for both her and Matt to not be at work due to a client, but she knew that it was actually because of his jealousy towards Matt and did not want her to be alone with him on vacation. The player explains to him in the elevator that she wanted to take the vacation with Lisa to show how grateful she is towards her as a friend, as if it was not for her, she and Gabriel would not be together and that she would have moved out of New York after seeing the picture of Gabriel and Cassidy. As he did not know Lisa was the one to confirm that the picture had been taken before he met the player because he thought she believed him.

The next day Gabriel is shown to be very aware of Cassidy's hatred and unfairness towards the player as she was abusing her position as the head of HR to harass and threaten the player about her work and relationship with Gabriel. After Cassidy had tried to tell him that the player had her head in the clouds and was being unprofessional he corrected her by telling her that the player's work was just fine and he didn't want her wasting his team's time anymore, and finished off by telling her yearly review was coming up and that he would be helping to review her which made her leave upset and with disdain to the both of them. He then asked the player if she was okay and to let him know if Cassidy bothers her again.

While he is away on business the player finds out that Gabriel had arranged for an all expedience paid vacation with plane tickets & hotel rooms to Atlantic City for her, Lisa and Matt for their vacation as an apology for denying their request in the first place due to his own jealousy towards Matt, but changed his mind after finding out that Lisa saved his relationship with the player and wanted her to give Lisa this gift. When Matt heard about the news, he was upset since he wanted them to pay for it themselves, and it made him feel like less of a man. Later on, he reveals to the player that he and Gabriel used to have a friendly competition on who could pick up the most girls at Starlite, which Gabriel would always win at because of his status and money, which made Matt afraid that Gabriel's feelings towards the player weren't genuine. When she stays at the hotel during her weekend vacation at Atlantic City, she's having a nightmare when Matt reciprocates his feelings to her.

In Chapter 3 during the nightmare, the player simply reject his advances until Gabriel knocks the door, making him tell the attendants to open the door using the card key. She knows that Matt disapproves of their relationship and she hates being caught by Gabriel once the door opens. The player finally awakens soon after having nightmares of getting caught by Gabriel when Matt is with her and she sent Gabriel a text message and cleaned up her face. She heard someone knock on the door in the middle of the night who turns out to be Matt. The player realizes that she accidentally sent the text message to the wrong person which was meant for Gabriel as Matt shows it. He convinces the player to stroll around in New York with him because of the beautiful lights and other restaurants that remained open for twenty four hours and the player agreed. During the stroll, she asked Matt to send a text message to Lisa but he refused because she was asleep and the two decided to play a game by trying to get to know more about their lives and their personalities and he finally learns about her relationship with Gabriel. Returning back to the hotel that she was checked into, they were seen drinking and the player reveals her dislike of hard drinks such as whiskey and that she prefer wines. After Matt leaves, she spends the night at hotel until she went home. That night after feeding her pet white Persian cat, she went to Gabriel's apartment unannounced, leading them to have sex when the player is stripping herself away to make love with him.

The next morning, Gabriel gives her a free permission after their romantic night and was given a phone call regarding about the emails from his employees. Despite doing work at home, the player continues to flirt and play with Gabriel and displaying his domineering side whenever they get intimate as they actually did making love before going to the office despite Gabriel had missed calls from his phone and he did not care so that he can focus on the player to make love for each other. After two hours, they manage to get through the company and Gabriel had signed a three deal and making a cocktail party for the charity. The player encounters both Jake and Lisa are having a fun conversation until she reaches through the elevator while being confronted by Cassidy. Inside, she berates the player because of her occupation as an HR manager while the player informs her that it was Gabriel who gave her the permission to work late after they made love twice, much to her horrible shock until someone wants to enter the elevator who turned out to be Mark who thanked her for letting him inside after he hurried to reach the elevator in a short minutes. Inside the elevator, Cassidy tried to ask Mark to have lunch together, but he refused due to his hectic schedule and he leaves. Cassidy also gave her a dirty look after this. Once she arrived at her cubicle, she met up with Matt who continued to mock her with his jokes as well as making fun out of Cassidy. He also informs her that Jenny is the one who finishes most of the files when the player had spend a weekend vacation in Atlantic City and she remarks that she was a machine just like Gabriel until Jenny arrives to see them and the player mistook her as Cassidy. They continued to make fun out of Cassidy as Gabriel arrives to see them and compliments them to keep it up.

As soon as Gabriel leaves after informing the player about calling to him because of his client in New York, Jenny receives a call regarding about the mall sales consisting of expensive brands and she invites her and Lisa while Matt refused due to his sideline for teaching the kids in the Gym. Jenny angrily informs him that she and Lisa are the guests and she will be the one to pay to shop their clothes (since she and her half-brother Ryan are a rich family). Few hours later after work, they managed to buy lots of expensive clothes and the jacket that Jenny didn't have those in her apartment. By the time they're about to get home, Jenny informs them about the muggers and the player remembers the time when she was a newbie, had her purse being stolen by a mugger right from the very beginning which results her getting stressed up. But when they talk about Jake since Jenny is not being protected without him despite the latter had a time off, she angrily raises her brow, displaying her dislike from her half-brother's protection because of Jake only for her to be scolded by Lisa which the player states that she was exaggerated when she scolds Jenny. When they arrived at the Gym, they see Matt sparring with Jake in a heavy boxing match that makes Jenny getting uncomfortable despite Jake's revealed appearance only to be scolded by him when he confronts her along with the player and Lisa. As Jake lashes both of them because of Jenny, he didn't mean it due to Lisa getting awkward over his yelling which leads him and Jenny to have an argument, resulted his decision to quit. Despite the outcome however, Jake tells Jenny that it will be soon since he doesn't want to break a contract with Ryan as Lisa knows about Ryan who is the current head of the company. Both him and Jenny continue to bicker about forcing him to let them come to the bar as Matt decides to come along and take a drink once he goes for a shower. As Jenny drags Jake into going to the bar reluctantly, the player noticed Lisa became interested to Jake and she informs him that Jake is a nice guy despite his plan of quitting his job as a bodyguard for Jenny. Before meeting them at the Half Five bar as she returns back to Carter Corp to give Gabriel the file reports, she overheard him talking to someone on his phone at his office which resulted him to violently hung up his phone. Much to her worry, she tried to check upon him as Gabriel opens the door, leading them to kiss each other inside of his office. Because of their intense love for each other, she tried to took off Gabriel's jacket and vest who is reluctant that he had an important phone call. To her surprise however, Gabriel did took off his tie and button-up shirt to make him shirtless as an opportunity to make love with the player which he did. After a few hours, she went to Half Bar to see her friends. This is how Jenny discusses with Colin about taking the trip to Tokyo because of the Japanese deal and to Jake's worry and disappointment while Matt continuous to make fun on the player while pretending he was defeated by her if she goes to Tokyo and the player threw him some pistachio shells to stop him. Since Colin had no concert with his bandmates, he let the DJ play lively songs as Jake dances with Lisa despite having no tastes in Lisa's sexy dances while both Matt and Jenny are challenging each other to do the sexy ballroom dances which the player became saddened if Gabriel was there for her. As the bar is about to close soon, she finally talk to Colin about Jenny as well as the annual reviews while Colin makes a crack joke to her because of Matt. Colin also tells her that Cassidy has no power to fire her on the spot while dealing the annual reviews because of Gabriel's affair with her. By the time Colin is about to say about the secrets of the company, Matt intervenes as he frowns and he invites her to his home for the last drink. As the player is about to get in the car along with Lisa and Colin while Jenny takes a back-ride on Matt's motorbike much to Jake's worry. The player soon talks to both Jenny and Colin which he never tells her about the company's secrets so she goes with Matt and Lisa. Here, Matt was oblivious between the relationship of Jenny and Jake as the player corrects him that Jake hates her. When he turns off the music, they overheard Jenny is having a fall out with her half-brother Ryan who talks to her phone, leading her to get home as Jake reveals about Jenny's dislike over her brother's protection. The player also leaves to Gabriel's apartment after they make an intimate text exchange, much to Matt's sadness. Arriving at his apartment, Gabriel keeps looking at his silver ring when the player asked him about his father which he ends up kissing with her as he keeps the ring on his pocket. Despite his plan to continue their intimate moments at his office, Gabriel refuses because he needs to focus on his work as Jenny is the one to handle the negotiations for the Japanese deal. The player tries to make promise if he do something intimate on his free time, instead Gabriel passionately kisses her agreeing to her promise as he goes to the shower when he took off his sweater and the player states that she will be with Gabriel forever.

The next day, the player is having lunch with Jake and Lisa at chez Felipe where they talk about their interests and hobbies. Lisa is revealed that she enjoys pole dancing while Jake reveals that he does combat sports such as kung-fu and horse-back riding. The player also tells them that all she does is watching television with her pet white Persian cat. Also, the player discovers Jake didn't notice about Lisa about her interest in him. Once they return back to Carter Corp, Lisa was frustrated since Jake's decision to get back home. The player convinces Lisa to go with him which she did as she kisses him, much to Jake's surprise and being informed to meet her at dinner which he agreed and the player was happy for them to make a better date. Back at their workplace, Matt was angry and frustrated as he tells her that Jenny went missing, much to her horrible shock and she is the one to negotiate about the Japanese deal and her disappearance also stresses both Gabriel and Mark, leading the player to find her and stating about her getting a bad vibe and not considering whether she is their co-worker or just being Ryan's half-sister as an influential even if she would risk her job in Carter Corp. for that incident.

In Chapter 4, the player is stressed out because of Jenny's disappearance only to be remarked jokingly by Colin while she asked him where Jenny is which he replied that he did not see her. When Lisa called her about Jenny who revealed herself in a disguise while arriving at the company, the player did not know that it was her brother Ryan who takes her to his company as she hurriedly goes to the elevator to find her only to be encountered by Ryan who is about to go to his office by taking the elevator. As Lisa leads her to find Jenny, she found her in a taxi where she has an appointment to meet someone and she rides the taxi and go off, much to the player's worry and was found by Jake who had groceries at his home. Learning that Jenny goes off, Jake allows the player to come and find her by riding a car given to him by Ryan. The player explains to him about Jenny who sneaks away from her new bodyguard from his first day which angers Jake. Arriving at the restaurant either the player or Jake were denied by the bouncer from the restaurant and warns them about an identity theft when they used Ryan's full name to get through. While waiting for Jenny at the car in Jake's orders, she learns that Jenny avoids getting call by him. Due to getting stressed out, Jake easily learns about the player's relationship with Gabriel which causes her worry because of his promotion. However, Jake knows that Jenny is interested in Mark Leviels which is their director and the player learns it. As Jenny gets out of the restaurant along with the client in his 50s after Matt had called her, they confronted her face to face as she was annoyed at seeing both of them and Jenny reveals about the Japanese deal has been pushed back in three days because of their important meeting with their ambassador. The player soon realizes her mistakes that Jenny never betrayed her brother's company she had currently had worked for and Matt was making a miscommunication with her which causes her doubts towards her. At the coffee shop, the player finally apologizes for the doubts she had given to her. Jenny accepts her apology and player remains to keep secret regarding about her current relationship with Gabriel as both Jake and Colin knew which is why she was doubting at Jenny into thinking she was betraying the company and getting a drop down over Gabriel's promotion within his career. Jenny soon reveals that she went off without informing either Gabriel or Mark about her own project where she discusses with the Director of the newly-opened hospital and showing her love of children who were patients. Because of the car chase happened, she scolds them including Jake and despite Jake's apology for what happened previously, Jenny angrily refused and pays their order and stomps away. The player soon apologizes to Jake because of her faults in going after her and Jake accepting her apology in which he would inform Ryan about Jenny's actions. Returning back to Carter Corp., she ignores Cassidy by the time she arrived at her cubicle while she was with Mark. Instead of talking to Matt about Jenny, she went to Gabriel and seeing him looking at the skyscraper as well as his silver ring. Since she didn't talk to Matt, Gabriel admits that he and Mark are looking for Jenny regarding about the Japanese deal and he received her text message that she went home due to the player's car chase with Jake. With that, both begins to get intimate in his office until Mark calls him which he informs him about the last file he had shared to him. Despite the intimate sessions with the player, Mark tells him that he has some business meeting with the French clients in Chicago at today's time where he takes travel to Chicago in four days and both he and Jenny has to sign the Japanese deal. Therefore, he picks the player when they're going to take business trips in four weeks at New Orleans as the player stopped when she is about to unbutton his pants after he let himself moaning over the player's kisses on his bare chest. As soon as Mark hung up the phone unaware of their intimate sessions at their office, the player apologizes to Gabriel for getting this far which he's not mad at all and he continued his romantic relationship with the player at the office by taunting her what he's going to do with her privately. Two days later, he visited the player's new apartment and the doorbell was damaged. Then, he tried to call the player once when she was still talking to Lisa on her phone regarding about Jake's rejection to her. The player soon receives his second call, informing her about his surprise. As the player opens the door, Gabriel was there and she hugs him as a reunion leading them to spend time alone during the weekends. The next day, she goes to meet up with Jake at Central Park which he reveals that he lied to Lisa much to her shock, and he changed his mind on going to Lisa's house and that it would hurt her, stating that he does not want to have any forms of relationship. The player soon yells at him in surprise and gives him some love advice regarding about any forms of a relationship which he smiles at her, telling her to tell Lisa about all this. He then takes her back to Carter Corp and seeing both Mark and Jenny. The player knows that Jake is now on their side and was happy to be with them, and never talks to Jenny because of their fall outs and also reveals to her that Ryan had fired some of the bodyguards when Jenny would sneak away from them.

After Jenny immediately goes to her cubicle because of the Japanese deal given by Mark and seeing herself be too stressful. The player was bored and decides to go to Colin's office. When she arrived, she was encountered by Ryan, the CEO of the company and she apologizes for leaving him impolitely when she was having an important business meeting she was attending to and Ryan replies that it's not necessary, informing her about Colin who is about to leave for his tour with his band mates in Philadelphia. The player then mistook Colin as someone else when he wore his casual attire while preparing his things. Colin seemed to know about Gabriel and the player when he had watched most of the surveillance videos caught on camera much to her horrible shock. Colin also informs her about the person who took a photo between her and Gabriel and left. Despite the player's pleas about the person behind it, Colin refuses and he tells her that he likes seeing them kiss and he laughs.

After Colin leaves for his Philadelphia tour for his Nightmareden bandmates, the player was surprised to have a victory party when both Mark and Jenny succeed in the Japanese deal which happens to be the Tokyo Branch of Carter Corp and Jenny gives a party toast to her co-workers. Unfortunately, the player tries to go with Gabriel but he refused and he points directly towards Mark if she wants to talk about something but was confronted again by Cassidy as she smells the stench of her perfume. She even berated her for her actions only to be interrupted by Mark who had a phone call, causing Cassidy to leave. Later, she meets up with Gabriel at the coffee shop to have a date after their victory party at the company. The player senses that Gabriel would officially make their relationship public after remarking that his corporate suits were old and takes a liking to his birthday suit and Gabriel complies that he will buy a new suit to impress her. Gabriel then asks her move into his apartment after being annoyed due to the waiter's presence because of their orders and asks her of why she didn't answer his question. The player accepts to live in his apartment, much to his amusement. He then watches the player eat a raspberry cake, remembering the times when she ordered this dessert at Felipe. He vows that he will give as many raspberry cakes for her as she wants. The next day, she had bumped into Jenny and this time she was shopping for her three week trip to Japan and the player learns that Jenny is interested in Mark and annoyingly tells her not to judge about their personalities. She then takes her to her apartment and drinks tea. Jenny then asks her about how her and Gabriel had started their relationship so that she can do it with Mark in their three week trip. She also reveals that Jake would be going with her as well and the player was shocked knowing that Lisa will be more disappointed once he tells her about it. Afterwards, she talked to Matt on the phone at her apartment, regarding about Daryl getting hospitalized. Gabriel visits her at apartment during her phone call and starts to seduce her as payback for her seducing him while he was on the phone with Mark. The player gives into him seducing her and the two have sex. After they finish, the player discovers that she was still on the phone and that Matt overheard their moans during sex and he abruptly ended his phone call much to her horrible shock, knowing that she broke his heart after he heard both her and Gabriel moaning during their love making.

In Chapter 5 while trying to keep herself calm from Cassidy's meddling, the player apologizes to Matt for what happened last night since he heard their moaning and this reveals his clear dislike for Gabriel's domineering ways and always mentions his brother Daryl when he was discharged from the hospital and was taken to the police station for questioning. He also tells her his reasons for keeping his call to her because he needed her comfort until it happened between her and Gabriel which makes the player decided to end the conversation about this. Matt also wanted to ask Gabriel if he can work from home and dismissively leaves her. At lunch, Gabriel takes the player to Chez Felipe to talk about her moving into his apartment as Gabriel wants to spend the weekend with her at the end of the month due to conflicting schedules. Therefore, she was visited by Lisa and they discussed about moving into Gabriel's place which Lisa decided to take her room from her apartment until she was contacted by Jenny who is still talking about Mark and suggested to the player that she has friends who can help her find a nice place for her and Gabriel to stay at and she thanked her before she hung up due to the meetings. The player also tells Lisa not to worry as she is worried about Jake and they celebrate together since Lisa decided to stay at her apartment.

The next day, when the player is on her way to Carter Corp, she saw a man in an suit, remarking this as being elegant and stylish (as she sees Steven for the first time) causing her to run away while the latter tried to follow her. During their long weekend vacation Gabriel takes the player in Miami, Florida as a surprise for her to spend time together by playing walking around in the beach. The player was surprised upon learning that Gabriel had rented the glamorous beach house to spend their weekend vacation there while ignoring Matt's calls from her phone. As Gabriel is about to speak to Mark on his phone, the player begins to take pictures of the entire beach house and share it with Lisa. When she was relaxing, she receives a call from her father instead of Lisa and describes her father as a full-time drifter and a half-rate explorer who made his dream a reality to travel around the world but caused a separation with his family as well as showing his cowardice when her mother was dying from her illness and focusing on his travels. Seeing his knack of money, both the player and her father had a heated argument because of his actions until she blurts out about Gabriel. Her father threatens about Gabriel's personality causing the player to get infuriated and angrily hangs up her phone. She later spends time with Gabriel at night at the Jacuzzi from their rented beach house and she finally tells him about her problems with her father as Gabriel also tells her that he shares the same way but in a different perspective. After their vacation weekend, Gabriel takes her to his apartment for a night until he receives a call from someone, leading him to get back to Carter Corp for emergency purposes and letting the player to stay alone. She then gets a missed calls and text messages from Lisa regarding about Matt's problems until Lisa called her about it knowingly that they think Matt was working for home but he went absent without leave.

In a meantime, both went to the place where Matt lives while she contacted Colin about Matt and they encountered his twin brother Daryl when she runs out of batteries and they pretend as his own friends who turn out to be Matt's friends because they can't enter because of the door code. As they enter, they noticed Matt was spending his time at his home along with his brother Daryl much to their disgust and angry after Lisa takes a small punches over Matt for taking his absence without leave only to be calm down by the player. When they are about to leave because of their hysterical laugh of their actions, Matt stops them and finally tells them of his reasons of coming back soon at Carter Corp by taking a crossroad to all around the places while Daryl listens to their conversations. The player still scolds him for his plans until she jokes him out because it was worth for him to do that road trip as she questioned herself about her future in Carter Corp. Matt decides to take them to Starlite as an apology to make them scared and worried and Daryl backs away uninterested, remarking the bar is lame as Matt tells him that he is not invited. As they spend the bar drinking cocktails and dancing all night, Matt decided to go home. Therefore, Lisa is dancing with a strange man named Seth and they took a selfie. She also asked the player if she has to show it to Jake which makes the player scolds her immediately because it was a very bad idea if she shows the photo to Jake and that would make him angry. She gives Lisa some advice until she receives a text message to Jake. As Lisa decided to make a smooth talk over Seth, Matt decides to get home as he takes the player back at her apartment who is almost asleep. Once she was asleep on Matt's lap knowing she was crying when he is about to leave and retaining her feelings to him, Matt reveals his affection to her and she is the only girl is the most specials than the other girls he had met. As the player awakens, Matt decided to leave and she wishes him goodnight.

The next night, Gabriel had a cocktail party as everyone is having a good time. She went to the manager's place to find him. She then found Gabriel and they talked privately at the meeting room before they parted ways. She then meet up with Lisa who is angry and upset and learning that Seth that she had met last night is a thief who stole most of her important things while he was sleeping with her. However when Gabriel decided to gave her a Japanese whiskey named Nikka, she refuses and decided to drink vodka instead much to his annoyance. Despite Matt's suggestion, Lisa refused and she didn't have the thief's cellphone number to be detected but that changes when they were talking about Jake. The player was assisted by both Matt and Lisa by taking the elevator at 42nd floor and to find Gabriel. As she found him alone in his office within the dark, the player asked him about his problem until Gabriel lashes her out, stating that Matt had went to her room during their stay at Atlantic City, much to her horrible shock. Because of Gabriel's hostility to Matt, he thinks he had slept with the player but she angrily denied. She soon explains to him about Matt taking her outside and drinking together with friends. Therefore, Gabriel cries emotionally and decided to break with the player for protection much to her sadness and upset and stating that she broke his heart.

In Chapter 6, she was given comfort by Lisa following the break up as Gabriel breaks up with her up for protection. The next day, she met up with Jake who became disappointed when she learned from Lisa about their relationship, especially to Jenny. Also, Gabriel formally apologizes for his actions to the player due to his strong emotional impulse and he reconciles with her by making out inside the elevator. The next day after spending with him at his apartment, Gabriel makes some breakfast for each other until his mother Holly visits him, causing him to hide the player at his room. Holly also shows her distaste towards the player and persuades her son to find another woman, but Gabriel stops her saying that he is not alone, unaware that she overheard their heated argument regarding towards her and the player simply leaves knowing of Holly's dislike of her. On the way after she talked to Lisa about Holly until she met up with Gabriel's father, Steven, who had followed her in the previous chapter while bumping into him with her coffee and learns her name from the coffee she was drinking and interacts with the player by wooing her. Then, she was forced to join Matt to go to Daryl's party at his villa by taking a motorcycle ride to get here. Although, the player enjoys the party but also shows her dislike to Daryl's advances by scolding him despite his interest in her until she received a text message from Gabriel, where he wanted to talk to her privately at her apartment regarding about the morning incident, much to the player's chagrin. Matt then goes to her and wants to know where she's going as the player decided to get home and meet with Gabriel and needs to get a taxi. Matt angrily insists that she needs to cancel it and he will take her home after he angrily thinks about Daryl's antics to her but it was Gabriel and the player noticed their animosity between them. The player refuses his offer until Matt reveals it was not his motorbike but borrowing Daryl's Lamborghini to take her home. The player finally tells Matt about Gabriel's mother Holly while inside the Lamborghini, it reveals that Matt couldn't move on because of the player and was always sticking up to the past. As soon as she gets out of the car, Matt became worried for her and wants to know what happened, Gabriel angrily showed up to see them, questioning the player on why Matt was there. The player tells him that Matt took her to Daryl's party. Gabriel lashes her out about the bad memory of the Lamborghini she was riding, regarding about the accident where she was nearly killed during their illegal car race. Despite the player's reason, Gabriel angrily ignores it. Following their romantic night, Gabriel continues his romantic escapade with the player in the morning before going to the company. While waiting at the elevator, she listens the tensions between Mark and Jenny and Mark angrily scolds her regarding about her work and soon consoles Jenny at the break room. Once Jenny leaves on her work duties, she was horribly berated by Cassidy who tries to observes her movements. When she was called at Gabriel's office, he invites her on a family dinner with Holly, much to her disdain. Before going to the dinner place, she comforts Jenny after learning that Mark aside from scolding her on her work loads, but also breaks her up during their date in their business trip in Japan and soon Jenny moves on by eating her homemade cookies and she shares it to the player.

As they go out on a family dinner with the player, Holly finally shows her bitterness towards the player for breaking her son's heart as the player rebuffs her that it was her son who caused her stress causing her to stomp away angrily at the restaurant, much to Gabriel's horrible shock. As the player leaves while she was talking to Lisa on her phone, Gabriel tried to stop her from leaving and he reassures her about their current relationship especially after she had angrily left them, he finally scolds his mother Holly for her horrible remarks about her while defending her by his side until Steven surprises them as Gabriel recognizes who he is. The player was surprised to see both Gabriel and Steven as father and son and they also displayed their strained relationship. Steven sarcastically remarks to his son that he's good to say it to Holly but he's the not the type of person he thinks he is and he tells the player not to worry because he's not going to bite her while winking. Gabriel then angrily questioned the player on how she met his father, showing his rebelliousness to him.

In Chapter 7, they stayed at the bar as the player explains to Gabriel of how she met his father Steven, until Steven admits that he followed her two days ago much to Gabriel's fury, and Gabriel also reveals that he paid the private investigator into finding him, and the player learns that he's taking the red tape for spending his money to pay the investigator and the declining of one of his credit cards and Steven became disappointed in him. Gabriel also claims that his father is lying for abandoning them as Steven also reveals that his reasons of leaving them is for their protection and he wanted to see him for a very long time, watching him from afar when he was growing up until his graduation and Gabriel tells him that he needs to think about it. Afterwards, Steven gave him his number to call him and leave but Gabriel remains hostile towards his father. He then apologizes to the player while staying at Central Park for not telling her about his past and went to the chess place where he reveals that Steven taught him how to play chess before his parents were separated and he accomplishes this by winning the chess competitions he had participated in. The player suggests that he challenge his father Steven to a chess game which he agrees, thinking that Steven would be a little rusty because of his age. As soon as they get back in Gabriel's apartment, they ended up making love for the rest of the night.

The next day, she meets up with Jake and Lisa as they went to the Central Park to have a private conversation. This reveals that Lisa and Jake didn't have a relationship at all but she lied over having a relationship with him which upsets Jake and is also the reason why Jenny is very upset towards of Jake. Later that night, Gabriel takes her to a restaurant to meet both of his parents while Holly remains hostile to the player. While drinking, it's revealed that Holly is trying to finalize their divorce papers to Steven while also keeping the surname Simons while she lives in Boston. Steven also ask the player about his ex-wife's suggestion which she agrees to but is not beautiful enough. Because of her hostility, Holly criticizes the player for breaking Gabriel's heart only to be defended by Gabriel, stating that her criticism has gone too far and he angrily tells her that she hurt him but he hurt her because he wanted his relationship with the player to be repaired. With that, Gabriel takes the player and leaves the restaurant and Steven angrily tells her that she hasn't changed. He soon takes the player back to the apartment to have a romantic moment again. The next day, the player went to Mark's office and it's revealed that Mark was looking for another job in pediatrics while he was talking to the employees at the hospital. Then, she meets up with Jenny and they overheard the conversation between Mark and the employee that are having an argument which he reprimands the employee to talk to their Director regarding about their special treatments to their employees. The player calls this as the Leviels incident when Jenny is about to speak to Mark about his problems. After talking to Matt, Lisa, Colin and Jenny about their recent problems in their livelihood, she visits Gabriel's apartment where Gabriel and Steven are there. He asks her to come to the casino with them, but she declined and both leave after Gabriel tells her that her mother Holly remained in Boston following the restaurant incident. After spending time at his home, she met with Steven who gave her some coffee. By the time she is about to get back to her apartment, she learns that Steven is a scam artist in a similar manner as Matt's brother Daryl, but is more focused on trying to smuggle the money from the casino at Atlantic City. The player now learns the main reason of Holly's separation from her ex-husband and Gabriel's initial dislike of him which is why she decided to warn Gabriel about the illegal attempts of his father.

At the gym when Matt sets off a boxing tournament, Jake was overpowered by Markus which resulted in him to throw the towel and give up the fight, much to Matt's disappointment. Lisa was jealous when Jenny became concerned about Jake, which lead to their argument only to be stopped by the player. She allows Jenny to try to reason with her bodyguard and inform Lisa that it is enough because she has no chance with him. The player then received two missed calls and text messages from Gabriel. As she reads it, Gabriel informs her that he was with Steven at Atlantic City. The player became saddened about his situation and she wants to warn Gabriel about his father Steven but it's too late. Knowing that his father allows him to play the casino, leading to his gambling addiction.

In a twist of turn of the events in Chapter 8, the player remained stress after Gabriel had received a text message. Therefore, Jake arrives back into the Gym with his boxing gloves on after Jenny convinces him not to give up the fight, much to Matt's relief. The player then leaves the Gym in a few minutes to deal with her stress despite Lisa wanted to come as she watches Jake beating Markus in a match. But Matt just followed her and comforts her upon learning she was crying. The player tells him that she will explain to him later as she decides to watch the end of the match and Matt lets her come back to the Gym. Once they came back to the Gym, Jake had won the match after beating Markus and he gives Markus a handshake as a sign of respect while he thanked Matt for putting him in the tournament. The player was amused and it was the first time she watches a live boxing match and Jake thanked her for that. Despite the laughter from her crack jokes, Matt tells her that it was still the tournament and the participants are here to win as well as helping the kids to win. This also develops a friendship between Matt and Jake. Matt informs Jenny about the first night and the next will be three nights and he asks the player to have a drink which she agrees so that she needs to get her mind off things. The next morning, the player discusses to both Matt and Lisa about the business in Atlantic City. As the two came by, this is how the player tells them about Gabriel's text message where he went off with his father Steven much to Lisa's horrible shock. The player also knows that Gabriel was cautious with his father as she informs him to be careful and not want him to be disappointed as he wants to know more of his past. She also informs them that it was Steven is the only person who can tell Gabriel about the same version happened which is different than his mother Holly's whether he trusts him or not. When Matt asks her if Steven has a gambling problem which the player confirms until Jenny arrives to see them who became stressed over Mark's strict behavior and she was looking for Gabriel and begins to fed up for all the things he had asked her to do. Since Gabriel didn't tell his employees that he left, the player lied to her that he was there to get a file while he had meetings with his clients until Lisa helped her when she was running out of ideas. Although, Jenny knows about Gabriel's troubles with his father Steven when he decided to travel to Atlantic City in which the player is trying to tell Matt and Lisa about it and they soon tells them about Steven who decided to rip off the casino much to her shock and Gabriel didn't tell her about this mess since he tells Jenny about it. As Jenny leaves, Lisa was shocked to hear about Gabriel's involvement with his father and Matt was not impressed about the incident. The player corrects Matt that Gabriel is not doing for the money but he do this for his father Steven and that worries her because of Steven's manipulation to his own son by emotional blackmail to make Gabriel helps him with his dirty schemes and being forced to be his partner in crime. The player also knows that Steven is a former gambling addict and he came up with a win every time. Matt was annoyed that what he did was cheating in a casino. The player to tells them that Steven insisting to prove his son that he overcame his gambling addiction while they spent the night out at one of the casinos and Matt angrily confirms that he is right when they celebrate in Atlantic City on a whim.

As Matt and Lisa leaves, the player decided get back to work and the last person she needs to talk is Cassidy whom she had bumped with and she replies to her in a sarcastic tone. Cassidy even threatened her not to use that tone on her, leading both into an argument which she attempts to fire her on the spot until her phone gets ringing where she receives a call from Mark where he asked her to eat dinner tonight which she happily agreed. By the time Cassidy left, the player suffers from vertigo and decided to get out of the building, thinking she was about to collapse. The player soon cries emotionally because of Cassidy's threats to get her fired until Matt arrives and became worried for her. He comforted her by hugging her amorously and she stops crying when he made a smile for her when he embraces her. Matt tells her that it is all right and don't let herself be pulled under while he keeps telling her about Gabriel being an idiot. The player tells him that it's not Gabriel but it was Cassidy and she made a statement that soon she wanted to get rid of her by firing and it was enough to do so. The player learns that it was Cassidy was the one who took the photos as she took one photo at the parking garage to that she can send it to her and she was pretentious enough to get surprised when she showed the photo to her and this continues her twisted little game. She continues to cry, learning that she's getting tired working at Carter Corp only to be comforted again by Matt when she is about to hug him as he kissed her on her forehead, sensing his tenderness on her. Matt decides to let the player come along with him with she agreed but she has to take care of things at the office. She also reveals about what she wants is more than life at the office with a job that she doesn't even really like anymore. Matt then reveals that he needs to put his hand in resignation in a few days and he never take Plan B on going to Carter Corp any longer once he comes back and he wanted to live this experience to the fullest as soon as he earns some money then he leaves the company. When he seriously decided to leave New York together, this causes doubts to the player and she can't decide whether she goes with Matt or remained with Gabriel.

Back on their work office, the player asked him about Matt's plans in which he wanted to keep things quiet. He then tells her that he doesn't know and he needs to think about it and he can't save enough salary he was making and he was waiting for the annual reviews to get a nice bonus for today's year. But for his emergency plan however, he decided to sell his motorbike, much to the player's shock. The player noticed his execution of his plans after the annual reviews which he confirms it in silence. As she comes in Gabriel's office, she found Jenny talking to the same employee that Mark had been argument about and she was the one who donated in the new hospital that Mark had been turned down his application in pediatrics and his four-year old son Nathan Leviels was refused to be admitted. The player learns about Mark's secret as a single father who is struggling to help his son Nathan to be admitted at the hospital to treat his rare disease. Jenny finally tells the Director of the hospital about Mark's current situation in his application as well as putting his son in confinement. The player became upset however when she learns that Gabriel had a secret affair with Jenny which is the reason why she keeps sitting around at his office realizing he was cheating on her for the second time. Jenny soon corrects her that she has no relationship with Gabriel and more focus on her work. She and the group are later invited by Matt to watch Colin and his Nightmareden band-mates for their final concert due to Colin being focus on his solo career (Referring to his good ending in his main story route). Therefore an anonymous caller had called the player on his phone who turns out to be Gabriel who is arrested for identity theft and being questioned at the police station.

Regardless, this is how Gabriel explains to her about his father Steven's real motives by the time he cheats to win in the casino. When the cops arrive because of this ordeal, immediately escaped and leaving his son being caught. Gabriel shows his angry and frustration over his father's manipulations. With that, he instructs the player to get his laptop from his office at Carter Corp. and he scolds her that his laptop is confidential which he kept his father's connections in order to stop his father on his tracks and to clear up his name with the help of his lawyer. The player agrees to get his laptop but became worried because of Cassidy's threats and Gabriel knows it. He tells her to go and see Mark to be given some time off and if not Jenny would told him the same.

Once she gets home after learning about Gabriel's arrest, she still dreaming about spending with Gabriel at Miami once he clears his name and being promoted as a Director which is Mark's current occupation. The next morning before sunrise, she immediately went to Carter Corp to get Gabriel's laptop at his office. She succeeded in getting his laptop only to be ran into Jenny who also came early as well after Gabriel had called her too. Jenny decided to team up with the player to negotiate with Mark in getting a four days time off which she accepts. Arriving at Mark's office, both became flustered when they saw Mark in shirtless who opens the door for them. He tells them that his shirt got spilled by his own coffee until his client had called him. Despite their embarrassment, they waited for Mark to get changed at his office closet where he is now dressed in his other suit. The player let Jenny to negotiate for their time off which Mark accepts but only need to inform it to Cassidy, much to the player's horror knowing about her motives of firing her on the spot. But Jenny is able to inform Mark about the email she had sent him which he reads it by turning on his computer and was happy that his application was approved by the Director of the hospital which he allows them to have a day off. Jenny and the player are able to take a time off and went to Atlantic City which she will take arrangements for their flights and booking in the hotels. Matt soon arrives and became worried when the player is still down. Because of their trip to Atlantic City, Matt refuses to come with them because of his animosity with Gabriel. At Chez Felipe, it reveals that Jake is coming with them and he also reveals to the player that Jenny is close to Gabriel but also keeping the secret about the player's relationship to him. Jenny arrives and she reveals that Jake is going to protect them just in case and Jake tells the player that he had one of the contacts from Steven and Steven was permanently banned in Las Vegas due to his cheating tactics in the casino. The next morning, they are at the airport while waiting for the flight and they were surprised that Lisa is coming for them. She informs them that she also negotiated with the manager and he agrees to have a day off. Her presence also causes Jenny to be disappointed while Jake arrives and accidentally fell off the tray of two cups of coffee because of her presence. Arriving at the police station in Atlantic City after taking a flight and getting a taxi, the player was getting nauseous and dizzy because of the unsettled surroundings inside the station, leading Jake to help her rest along with Jenny and Lisa. Jenny tells them that the police station is just like the hospital and she needs someone to go with her to see Gabriel at prison. The player became crucial in which person she's gonna help her is just like how she chooses Gabriel over Matt. She chooses Lisa over Jenny to help get inside the police station, much to Jenny's disappointment.

She then handle the cops while giving a laptop to Gabriel but they failed to find him. Jenny reveals that Gabriel had move to the other building after he fainted. It was later revealed according to Gabriel that the cops who interrogated him are trying to find his father Steven. As they eat dinner while staying at the hotel, Gabriel calls her and they reunited in the lobby which Gabriel informs her about his release from the police station and was trying to track down Steven. Gabriel angrily rants about his father Steven when the player tells him about their relation, stating that he will be rot in prison. Taking him to her hotel room, this is where Gabriel tells her everything in private about his secret life within his family. Steven became regretful for his actions into thinking he overcame his gambling addiction and it turns out to be a facade as he was man hunted by the authorities due to his cheating to win at the casinos and disappearance upon sight when he uses fake identification cards as it means he can enter the casino unnoticed. In his high school days, Holly reprimands Steven to stay away from him. The player convinces Gabriel to call his mother Holly about the incident which he accepts, especially mentioning his mother had a cancer which is why he was focused on his current job and his promotion in Carter Corp. Once Gabriel tells her about the money, she informs him about his knack of money much to his anger and frustration. Gabriel tells her that he also used a fake identification card to play the casino but was caught and he wanted to get to the bottom of his mess and for what Steven had done for him. He also asked the player if she still loved him even if he did something illegally. The player still loves him much to Gabriel's excitement and he is already a free man after getting released. Returning to New York in the middle of the night, she romantically spends time with Gabriel at his apartment until it was interrupted by their respective phone calls. Gabriel learns that his mother Holly was in a critical state due to her cancer while the player received a call from Matt who has problems in handling Jenny's files and causes more trouble on work.

In Chapter 9, She rethinks about Matt's problems of handling Jenny's files until Gabriel had called her stating that her mother Holly is in stable condition and was subjected to chemotherapy. The next morning, she met up again with Jenny and both talked at the empty conference room. This is where Jenny tells the player about Cassidy's past life and how she was separated by her abusive husband. As the two parted ways for their work duties, she was called by Colin and went to his office. After telling her about his tour for his solo concert, Colin finally shows the primary suspect behind for taking the photos between her and Gabriel during their relationship and knowingly it was a woman who talked to Ryan about their relationship. The player thanked him for showing it and now she learns who the real spy behind this company. She soon meet up with Matt at the break room who had problems about the missing file. The player decided to help him until she stays with him for a night. After recovering a few pages from the missing files, she takes a break with Lisa and Colin and Colin reveals that he will move to Los Angeles, California and starting his new life by taking tours as a solo performer and at the same time he keeps joking about flowers where the waiter had remarked him, much to his embarrassment and the laughter of the two women. Also, Colin will be replaced by a fellow programmer named Carrie Kang when he will be moving away in the company. Matt soon arrives and he informs the player about Jenny who reveals to scold at him for losing the important files. After work and staying at Gabriel's apartment, she supports Gabriel when he was depressed over his family problems by defending her from his mother's criticism, being tricked by his father into joining with him at the casino and his mother suffers from cancer. He thinks that his own family has been cursed, only for the player to reassure him and allowing him to get rest. The next day, the player arrives at Carter Corp to see crowded people are blocked by the security. As she checks around the city, she was blocked by Steven, who wanted to borrow her cellphone to call Gabriel. The player learns how terrible Steven is for what he had done to his own son, she refused and decided to get back to Carter Corp. Steven immediately grabs her arm while attempting to get her cellphone only to be pounced by Gabriel who is just in time to rescue the player. His push also caused Steven to get panicked and slips into the ground and bumped his head into the concrete, injuring his head while being knocked unconscious. Gabriel asks her if she is okay, which she replies that she is fine. However, more crowded people are screaming over at Steven's body and his blood is spreading quickly into the concrete knowing that his head injury is getting worse.

In Chapter 10, it reveals that Steven's ear was cut after he checked on himself following from getting pushed by Gabriel and became hostile to his son causing them to have a fall out and blaming the player for changing him. Gabriel angrily rebuffs his father stating that he shouldn't blame her for his faults while trying to defend her from him. Their fall out was interrupted by the security guard at Carter Corp. causing the latter to take him on his office for first aid as Steven plays along. The player soon reveals Gabriel's plan is to lure his father into his trap similar to the game of chess. At his office, Gabriel treats his father Steven with first aid on his wounded ear which is painful enough for him to reveal his plans. Although, Gabriel nearly choked his father for abandoning him especially for what he had done to him. The player intervenes them to make Gabriel stop as he let go of his father. Steven immediately apologizes to Gabriel for the screw up he had made to him as the player knew his dirty schemes. Steven also gave Gabriel a gift which is a red silk neck tie and Gabriel appreciates it. Although the tie is actually a tracking device so that Steven would manage to cheat to win for contacting him and soon leaves. The player angrily scolds Gabriel for manipulating him not until he contacts Colin about the trap which he informs him that he kept his phone on his suit when he recorded their conversation., much to his disappointment and the player finally understands about his trap became backfired. She soon encounters Jenny who wanted to ignore her for a while. Jenny remains complain about herself and the losing files that Matt had made as she tells the player about it and thinking about Matt's serious mistakes about the files as she covers up for him until Jenny leaves after informing her to tell Matt that she can defend him. That night, the player continues to get bothered about her conversation with Jenny as well as the animosity between Gabriel and Matt. She decides to visits Gabriel at his office as she knocks the door three times. This is where she overheard someone is with him, laughing. She finally pushes the door and noticing that Jenny is with Gabriel which make them in a horrible expression towards her. Gabriel tells her that the player came here to ask before she go while giving her an apologetic look. She also informs Jenny about the solidarity of the company when people begins to back stabbing each other to get raises and promotions at their annual reviews, surprising them both and they laugh at her statement. The player also noticed the two were close and Gabriel tells her that he and Jenny are working together for the sensitive file and she sees his message very clear. As she leaves the office, she was disappointed about their actions. Back at home to spend time with her pet white Persian, Lisa emotionally visits at her apartment and learning that she was fired in Carter Corp. due to her manager didn't sign up her vacation days in Atlantic City which results her in AWOL and giving some sanctions to her job. The player realizes that some of her friends will soon leaving Carter Corp.

The next day, she receives a call from Lisa and informs her to find a suitable job besides Carter Corp. Then later Gabriel calls her to go to Carter Corp to work while he went to the hospital to visit his mother Holly. Arriving at Carter Corp, she works so hard on her job because it was today's annual evaluation. Upon arrival at Mark's office, she was blocked off by Cassidy who begins to humiliate her inside of his office while waiting for both Mark and Gabriel to arrive. She even berated her to make both Matt and Lisa get fired in a hellish way until she bumped on both men who is now getting mad at her harsh remarks making them surprised. Here, this is where Mark shows his strictness and temperament to both women. Despite Cassidy's remarks over the player, Mark simply jabs at her about the problem of not informing him sooner. Therefore, he sees the player getting stressed of not sitting around at the conference table which he knew Cassidy didn't offer a seat when she arrived at his office which she confirms. Mark gave Cassidy a dirty look stating about her losing her good manners to her employees such as the player and the higher officials alike. Clearly, Gabriel knows that Mark is defending the player from Cassidy since he was on her side. Now the evaluation begins as despite Mark's offer them some water and coffee, they refused. He finally said the first evaluation about working along the company in a very simple way and Gabriel was there to compliment the player's remarkable work and her professionalism. Not until Cassidy continues to complain about the player while abusing her power as an HR manager only for Mark to shrug it off despite the player who keeps her cool from her verbal attacks. The player states that the work is demanding but interesting and the team is pleasant to work on a daily basis and Mark responds to her in positive terms much to Cassidy horrible shock.

As Mark continues to evaluate the player about her ambitions, Cassidy interrupts who is now angry and disdain over the player's meddling which angers Mark by slamming his fists on the table and both were surprised to his temper. Mark had been sensing Cassidy's awful behavior for weeks and always listening to her complain and for criticizing her co-workers as his patience is running thin. Now he knows she had went this far and using her position as the Human Resources Manager does not gave her unlimited power, showing her abusiveness in power as her advantage and angrily scolds her not to question of what he had said as well as in his office. As both Gabriel and the player look on to see the scene, Mark angrily tells Cassidy to leave his office immediately. She soon apologizes for abusing her power as a Human Resources Manager and glaring the player thinking she has a misconduct on her work until she bursts her bubble about Gabriel's relationship to the player much to Mark's surprise, exposing their secret to him. The player was stressed after all this time she brought it up during her annual review and the reason she keeps messing with her. Despite the exposure of their secret, Mark clearly understands them since he actually knew Gabriel and the player's relationship for a long time. Knowingly he recognizes about love when he sees it and making the player to forgive Mark for not saying this to him about her relationship with Gabriel and Mark tells her not to worry as he finally understand them more. Cassidy felt herself getting defeated even after she exposes their relationship, leading her to threat Mark to prevent a disaster from occurring in the company and she is not afraid to any of them when she is about to set in motion. Gabriel berates her that no one is afraid of her as Cassidy storms off the room in upset. Both men gave her a hearty laugh after she storms off the room. Mark soon reveals that it was just a preamble and the player's actual evaluation is about to begin and letting Gabriel to leave his office so that he can evaluate the player alone. During the evaluation, the player informs Mark about Matt's bonus which makes Mark refused and accepting her commitment and informs her not take it too far stating that she cannot challenge made by the manager's decisions. The player soon pointed out that it was Gabriel to punish Matt because of the missing files and learning that he was very sneaky to have his revenge on Matt without telling her and seeing his professional code of ethics. Mark tells her to meet Gabriel to know more about the details and he simply knows more than he is. Now the interview is over, she thanked Mark and he was proud of her as she leaves back to find Gabriel. This is where the player returns to her desk in the middle of the night for work, Here, this is where she had thought about Mark's evaluation to her and his disciplinary actions towards Cassidy for her mistreatment towards her employees including her and her abusing of authority and she was relieved that it would be a good lesson for her. Therefore, she saw Matt who is ready to leave the company and gave him a friendly hug. He smiles to her that he's going to leave and the player would never forget him because of the things they have been through to their work. Matt even stated that after all these years, he realizes that the most important person to him is the player and his life would never be so boring when she they first met and yet he complimented her for being so beautiful. Despite their sweet conversation as well as the itineraries for their various trips regarding about leaving New York to make the player decide to come with him, Gabriel had caught them and he's been watching their conversation the entire time. He decide to leave them abruptly much to the player's dismay and Matt allows her to find Gabriel, telling her to let him know if she changes her mind to leave town tomorrow. Once she finds Gabriel, he ignores her completely as she stops the elevator so that the two would talk about it inside the elevator. She soon explains about Matt being her colleague only for Gabriel to scold her, stating about Matt gave her a holding hand in the middle of the office until the player reveals that he has no problem staying late at his office with Jenny and aware that both were close. Knowingly that Matt wants her to come for a road trip, the player rebuffs him that Matt was just offered to her to go with him and she didn't gave him an answer. The player soon answers to Gabriel's gallant questions if she accepts that if he had waited a little longer, he would hear her saying that she'll never go with Matt and her place is with him, much to his relief. He whispers to her ear and he apologizes that he had thought their relationship is over and she would accepting Matt's offer to come with him and leave, making him to kiss her. The player reassures him to have another date but Gabriel refused and decides to get home and rest and leaves the elevator. However, she sees his angry and frustration at the lobby knowingly that Matt was resigned and he did not fire him on the spot before leaving. Now that the player learns that Matt has resigned at the company which is why he decided to offer the player to come with him and leave New York following his resignation.

The following day, she visits at Jenny's house where Jenny gives her some Gyokuro tea and cookies. They finally talk about Jake much to Jenny's dismay as she tells him that Jake had found a new bodyguard job and she does not know where he was. The player wanted to say goodbye to Jake until Jenny reassures her that Jake goes on a temporary mission and he will be back soon then they talk about guys and to the player's worry. Despite all this, the player know that she can't be living single life for long which Jenny angrily complies and it was just a tease. Then, they soon talk about the annual reviews and Jenny does not have an evaluation like they do. She reassures her that she will have that soon which she thanked her and they talked about Lisa getting fired. The player receives a call from Lisa when Jenny has to refill some hot water from her teapot. Lisa soon warns her about Jenny who wanted to get the job as a Manager like Gabriel and also believes Jenny had a relationship with Ryan Carter the head of the company. The player still believes in Lisa's fact, not knowingly that both Jenny and Ryan are half-siblings as Jenny continues to offer her some tea to refill her cup. Later, Gabriel tries to make a surprise for the player in a blindfold to see the HR's office which happens to be Cassidy's office. The player joked at Gabriel to surprise her for Cassidy's office as Gabriel tells her that it's for her and he reveals that Cassidy is about get fired tomorrow regarding about her awful behavior earlier, much to the player's joy and excitement. She also asks Gabriel who made that decision, and he reveals that it was Mark who made all of the paperwork and stating that Cassidy has been a problem for a while. While celebrating to get themselves free from Cassidy's meddling, the two had a romantic rendezvous and the player tells him that he shouldn't give temptation in this office. Nonetheless, Gabriel continues to get intimate towards the player much to the player's protest and someone had took a photograph of them in a flash and immediately left the scene. The player ends up tripping into Gabriel and crashed into the floor. To her dismay, the photographer is nowhere to be found after she fell off with him. Gabriel decided to find the photographer who is behind for taking photos with him and taking it back causing the player to blame him which he apologizes to make a better surprise for her next time. The two smiles afterwards and they went down to the elevator to enjoy their closeness. As Gabriel leaves back to his office for his phone call, the player instead of waiting for him at the lobby which she did. Arriving at the lobby, she encounters Jenny who is revealed talking to Gabriel at her phone. The player eventually mistook them for being together since these two are teaming up to apprehend Steven the other way. With that, the player leaves as the faintly collapses. Once she wakes up, realizing for herself that she was felt betrayed towards both Gabriel and Jenny.

In the final chapter of the story after regaining consciousness from collapsing, she takes a break at the Half Five to ease up both her stress and pain, remembering the times she was flirted by Gabriel when they met at his office, leading to their current relationship. However, she was mocked by other customers who were also co-workers from a different company as she was dragged away soon by Colin. Colin also reveals that he destroyed his badge and deleting his access using his hacking skills which also hints his resignation at Carter Corp while showing the visitor badge to the player and also encountering his replacement Carrie. Colin informs her that Ryan allows Carrie to investigate about the paparazzi who took the photos between her and Gabriel, much to the player's unwillingness. Matt soon arrives at the bar to see them. This is where the player still think about her problems regarding between Gabriel and Jenny especially she couldn't answer about Matt's offer on his road trip. She wanted to say this to him until it was interrupted by Lisa. She tells him that Matt was talking about his road trip which she asks Matt if she's going to go on a road trip to ease up her scenery but Matt was dismayed at her until Colin arrives with their respective cocktails. This reveals Lisa's problems of losing a lot of money and she has no money to pay for the rentals. Despite their suggestion to let them stay, the player suggested to let Lisa stay with her family despite she's being rebellious to her father. After toasting to enjoy their own farewell party, both Lisa and Colin are finally parted where she is about to catch the last train while Colin will miss both the player and Matt since he is about to go on a solo tour in Los Angeles, California. Both her and Matt pass on the warehouse while walking around the cities in New York where Matt decided to sell his motorbike. Once arriving at his home, the player wanted to tell Matt about her answer regarding on his offer, Matt interrupts and instead taking her home by getting a taxi. The next day, the player cracking jokes on her own, imagining about someone else to work as Matt's replacement following his resignation. It was then that Mark informs everyone that Jenny is about to leave Carter Corp for Japan to make her own hotel and restaurant business, much to the player's doubt stating about their conversation and their secret phone calls. Before break time, the player gives herself some fresh air while showing her doubts about Jenny who arrived to see her and the player wants to talk to her. This is where Jenny reveals her true perspective on leaving her older half-brother's company for making her own business in Japan and she had been planning it for several years. She is also nervous because most people including her are there to hear the official announcement that Mark had made. Outside the company and meeting with Jenny, this reveals Jenny's decision of making her own business in Japan with the help of the managing director. Once she goes to Chez Felipe, she found out that Jenny is talking to Holly which hinted that the director she was talking about is Gabriel who is now promoted as the Director of Communications. The player became disappointed after learning of this and she is now soaked with heavy downpours when the thunderstorm came up. Arriving at Gabriel's apartment, Gabriel was the one who open the door for her which led to their make love sessions. After that, this is where the player questions him about his trip in Japan and Gabriel admits about his promotion especially about how Jenny was happy to speak out about him. Gabriel finally clarifies to her that he doesn't work with Jenny and all he did was just giving her some business advice due to both sharing their ambition in their respective occupation as he remained at Carter Corp. because of the presence of both Mark and Ryan and Ryan is actually Jenny's older half-brother which makes the player think about both of them had a relationship but they were familial. Gabriel also convinces the player to come with her in Japan to learn about their cultures and living in a new apartment at the expense of both Mark and Ryan while trying to give her advice to follow her instinct and the player tells him that she needs to think about it. The next morning, she became lost in thought while trying to think whether she goes with Matt on his road trip or Gabriel's proposal to come with him in Japan and seeing all of her co-workers were finally departed at the company whether they get fired or taking a resignation. She soon goes with Gabriel to have a breakfast after the latter prepared it for her. The player remains stoic since she had never tried living in different cultures until Gabriel receives a text message from his mother Holly while the player informs him about Holly's meeting with Jenny who stated that her meeting with his mother is a top secret, much to his surprise. Gabriel rebuffs her that she had met Jenny when she was hospitalized and also reveals that she gave her and Jenny some invitation letters and telling her that she finally apologizes for her mistreatment that she gave her when they met. As they finally leave Gabriel's apartment, he pointed out the wedding billboards regarding about the wedding expo and to the player's disappointment. He soon gives her a cab because he decided to visit his mother Holly at Boston. Arriving at Carter Corp, she was blocked by Cassidy from the cab door after getting fired by Mark. She furiously blames the player for her various troubles as well as her own future holds in the company she had worked for was ruined because of her presence, finally instigates a brawl between her and the player causing them both are having a catfight. Cassidy attempts to punch the player in the head while defending herself only for her to get pushed by Mark who witnessed the ordeal. He furiously threatens Cassidy to call the security before she threatens the player one final time. Then he immediately orders the player to come to his office in a fit of rage. Inside the office, Mark angrily reprimands the player for the catfight with Cassidy despite she was the one who instigates the catfight as the player tells him that she was forced to fight her by hand but Mark would not listen even if she is concerned because of Gabriel, he tells her to get her out of the office before he would make a sanction for the incident. The player was disappointed about the awful treatment the company has done it for her and sarcastically tells Mark that she enjoys beat the hell out of Cassidy, much to his horrible shock. Before he could sanction the player for her unprofessional behavior on the catfight earlier, the player decided to quit after remembering the farewell party with Matt, Colin and Lisa at the Half Five who were either resigned or being fired. Mark angrily justifies if she was making a joke but the player calmly tells him that she is serious to quit the company and thanking him for his kindness. Mark sadly allows her to go to the Human Resources office to sign the resignation papers.

Despite of resigning, she went to Gabriel's office and always had a phone call with his clients. The player finally tells him about her secret where she was almost getting married by her ex-boyfriend who took off the wedding as a runaway groom for her best friend which is why the player became dismayed after seeing the wedding ads as well as where Gabriel talks about marriage. Gabriel wasn't mad at her after all since he angrily tells her that her ex-boyfriend is unforgivable for abandoning her in the altar to exchange their wedding vows. He also reveals his secret as well where he keeps the alcoholic bottles on his office to celebrate. As soon both are kissing and making out, they almost got caught by Jenny who knocks the door at his office. She informs Gabriel about the lunch meeting with his client which he accepts especially when she say hi to the player before leaving. Both laughed since she almost caught them. Despite keeping secrets and for the player not to question Gabriel any longer because his meeting with his client at lunch was confidential, Gabriel informs her to meet his mother Holly at Chez Felipe, telling her that she needs to be on time. Before they take their separate ways, Gabriel asked her again which the player couldn't answer his questions knowingly that she is resigning at Carter Corp because of Cassidy who is now a disgruntled former H.R. who started and instigated the catfight and the mistreatment she had with Mark who holds her responsible for instigating the catfight as Cassidy was behind it. Arriving at Chez Felipe to see Holly who waved at her behind the table. This is where Holly apologizes to the player for her horrible remarks at the restaurant where Gabriel meets the player for her and Steven. It is revealed why Holly spoke to her so horribly because of her past relationship with Steven and how she shares her relationship with Steven to her and because of his bad habits due to being blinded by love, she was completely upset and she did not want her son Gabriel to meet the same fate as her with Steven. Despite this, she finally accepted the player who reminds her in her younger years for being passionate and thoughtful. She also informs her about Gabriel's plan to go to Japan and Jenny decided to accompany both because of her love of Japanese culture. With that, they begin their friendship as they order their respective Italian food. After that, she was surprise from a van's horn as it parked to reveal Colin who drove the van. Colin also learns that the player also resigned and asking about Matt's offer. The player tells him if only if he could tell her sooner. Thanks to Carrie's hacking skills to get the computer files, it was revealed by Colin that Ryan's intern Thomas Gordon was behind for taking camera shots towards unsuspecting employees in all departments and now being questioned by the authorities. Both Colin and Carrie teamed up to locate Thomas who was talking to the accomplice who immediately leave. She thanked Colin for his information which he thankful enough to help her get information and decided to leave by riding his van. They say farewell in Japanese but Colin was confused on the player's word which she translates him as "See you later" in Japanese, much to his happiness and Colin takes off with his van. On the player's last day after finishing most of her work loads she decided to get back to the apartment. She soon encounters Ryan at the elevator and this is where Ryan confirms about Thomas' job as the intern and he allows Carrie to take all the evidence to the police using the jump drive and delete all the inappropriate ones so that Gabriel's current job would not get in scandal. Ryan also learns the player's resignation according to Mark and he allows the player to help with Gabriel's current work duties in Japan as the Director of Communications along with Jenny who finally reveals herself being his half-sister (step-sister in the game), much to the player's surprise and Ryan also knows why Jenny's last name is Blake instead of Carter when she introduces to the player. As the elevator goes down, Ryan smiles to the player and leave. She later receives a photo between Jenny and Gabriel by an anonymous, causing her to get mad. As she arrives at Jenny's apartment, Jenny opens the door as the player was angry because of the photo. Knowing that Gabriel was not there it was someone else, Jake arrives to see the girls and Jenny slaps him in the face, much to his shock and the player realizes it was a total misunderstanding. When Jenny learns the photo between her and Gabriel, she frowns and stating who's responsible. Learning it's from the anonymous user, Jenny states that this is where she gives Gabriel a friendly hug and became surprised when the player learns from Ryan about them being half-siblings. While toasting drinks for their friendship, this reveals the relationship between Jake and Jenny, leading the player's decision to leave not to interrupt their romantic privacy. While looking for a taxi, she receives a text message from Matt who mistakenly thinks that she accepted his proposal to take a road trip with him by selling his motorbike and packing his stuff on his apartment. The player knew it's going to hurt Matt if she answers his question but it was a no. She decided to go to Gabriel in his travel to Japan and rejecting his romantic confession. Getting rejected, Matt immediately hung her up from his phone and at the same time he blocks her number from her phone to avoid contact with him anymore before she could send him an apologetic message. The player knew that Gabriel was right and her friendly relationship with Matt is getting doomed to fail. After returning to her apartment to get dressed, she meet up with Gabriel at his apartment who prepares their romantic dinner in a Japan theme. He prepares a plate of yakitori, a sashimi and a bottle of sake. This reveals of why Jenny is with Gabriel because he is her right-hand woman who aids him to entrap Steven by playing a game of chess as one of the chess piece has a hidden microphone especially Jenny's. She plays an accomplice into going with Steven to drink coffee at the coffee shop as he arrogantly confesses about his crimes, leading to his arrest by the authorities. Gabriel was relieved that he is now free of his father's mistreatment while frowning because it was the solution to put a stop to his illegal antics in gambling. When Gabriel asked the player about going with him in Japan which she confirms her decision to come with him, much to his enjoyment. Gabriel soon asks her if she informs it to Carter Corp which she is after being talked by Ryan about going to Japan despite her resignation on the company and both decided to travel to Japan as their very first adventure, together.

The bad ending takes place after the player decided to take resignation at Carter Corp following her personal catfight with Cassidy and the current mistreatment being given by Mark who is about to sanction her actions. Her relationship with Gabriel takes a broken turn when her meeting with Holly at Chez Felipe became soured just because she protects her son and almost had a near catfight inside the restaurant. At the Central Park when Gabriel attempts to apprehend his father Steven by playing the game of chess with Jenny and Jake was in his side, the player personally interrupts their trap and angrily scolds them from their lies, leading Steven to sense his son's trap and became mad at their actions. Steven eventually leaves the premises, much to Gabriel's fury and blaming the player for his failure to catch his father. Because of the player's stupidity and learning about the failed lunch meeting with Holly, Gabriel remains angered and decided to leave back to the office in upset. Seeing their current relationship has finally take a broken turn, she also asks Jenny of why she is with Jake which she admits that they had a relationship and was made a secret as well as correcting her that Ryan is his half-brother (step-brother in the game) and not somebody else. She later visits Matt at his apartment and he learns that the player had resigned the company. She noticed that his things are already packed and knowing that he's going to leave in the weekend. Because of the broken relationship she had with Gabriel, she knew that she likes Matt, much to his happiness which led themselves to make love at his apartment knowing of his feelings to the player and his dream was fulfilled. On her way to her apartment, she receives a video call from Colin who is now at the Venice Beach and informs her about Thomas Gordon being detected by Carrie who is now apprehended. After that conversation and he hangs up, the player was amused on his intelligence when it comes to computers. As soon as she packed her things, Lisa visits her and the player allows her to stay in her apartment while she was away and to look after her pet white Persian. Therefore, Gabriel arrives and gives the player a bouquet of flowers, much to her awkwardness. As Lisa leaves, the player decided to end her relationship with Gabriel as he sensed that she was already with Matt when he questions her. Gabriel then apologizes for his faults and allows the player to keep his flowers to remember him by and thanking her for changing him during their former relationship and leave. As the storm comes up, she was helped by Matt and telling her about Gabriel who visits at her apartment which she was relieved that she started to have a relationship with Matt. Matt comforts her nicely since the two are already together and they can travel around the world in a few days. The player was happy that Matt is always by her side in a loving manner.

## Allies

* The Main Character (Gabriel)
* The Main Character (Matt) (sometimes)
* The Main Character (Ryan) (sometimes)
* The Main Character (Colin)
* The Main Character (Adam)
* The Main Character (Daryl)
* The Main Character (Jake)
* Mark Leviels
* Lisa Parker
* Cassidy Sparke (formerly)
* Jenny Blake
* Holly Simons
* Jake Stewart
* Ryan Carter (sometimes)
* Ashton Darrow
* Felipe
* Laure & Anne Stewart

## Enemies

* The Main Character (Matt) (sometimes)
* The Main Character (Ryan) (sometimes)
* Aleksei Votiakov
* The Bratva
* Matt Ortega
* Cassidy Sparke
* Ryan Carter (sometimes)
* Alicia Boone
* Steven Simons
* Dad (The Main Character (Gabriel))
* Thomas Gordon
* Creep

## Relationships

*Gabriel and Matt*

*Gabriel and Ryan*

*Gabriel and Mark*

*Gabriel and Lisa*

*Gabriel and Holly*

*Gabriel and Jenny*

*Gabriel and Cassidy*

*Gabriel and Jake*

*Gabriel and Steven*

## Trivia

* According to the author and creator of the game, Claire Zamora, Gabriel is based on the real-life actor Chris Hemsworth.
* He shares a similar surname, Simons, with Janet Simmons from Fallen Road.
* He was the very first love interest in the series, due to him being the main love interest in the very first Is It Love? game.
* He is from Boston, Massachusetts, and is a graduate from Harvard University (which is also in Massachusetts).
* He shares his rebelliousness to Adam Peterson where both had a strained relationship to their respective fathers (Steven Simons and Mr. Peterson) but in a different perspective.
* He's been in the least secret images compared to the other main love interests.
* He's one of the 8 original characters and one of the 5 original love interests.
* He's one of the 4 characters with a Facebook account.
* In the beginning of Ryan's route, the player was revealed to playing Gabriel's route before the blackout.
	+ It is possible that the player from Ryan's route was attracted to Gabriel before she met Ryan due to her playing his story route.
* He was the first love interest that had sex with both an antagonist (Cassidy Sparke), and the main character.
* He was widely disliked by many players for his behavior in season 1, which has made many players hesitant to read his season 2.
	+ The writers are also trying to ruin Gabriel's characteristics, where players are criticizing his actions, especially in Chapter 7, where he also shares his father Steven's knack of gambling. But that changed in Chapter 8 where he was left by his father and was arrested by the authorities, leading his decision to capture his own father.
* He's the first character that has had both of his parents appear on screen.
* He was the first character to confirm that he had studied at Harvard.
* He, Colin Spencer, Mark Leviels and Ryan Carter are the only Carter Corp love interests to not have started off as second love interests in a previous story route.
* Gabriel does not have any real male friends.
	+ He and Matt actually used to be friends but started to have spite for each other when they got too competitive over women.
	+ Gabriel only has professional relationships with Mark and Ryan and doesn't speak or hang out with them outside of work, (Gabriel more than likely dislikes Ryan due to jealousy from the first season) he doesn't know Jake and Colin that well, he dislikes Matt and hates his father. He only gets along well with women.
		- This can probably be blamed on his father, Steven Simons, for abandoning him as a child which led him to not being able to trust men since he never had a proper father figure around. Which is why he only trusts and confides in women.
		- He is friends with Ashton Darrow however, but only in Jake Stewart's route.
* He can be considered as the third "love interest" in Jake Stewart's story route due to his interest in the player and the connection they make.
* Gabriel and Ryan Carter are the only main love interests that have never appeared in another main secret image during another story route, they have only been seen in images from their perspective story routes.
* His astrological sign is revealed to be Leo.
	+ Which means his birthday is between July 23 and August 22.
* In one of his extra love scene where Gabriel made the player strip naked when he beats her in a game of poker, referencing the adult game, Rei Poker where Evangelion character Rei Ayanami was stripping naked if the player beats her in a computerized poker game.
* Gabriel replaced Matt Ortega as the male best friend for the player in Jake Stewart's story route. Many fans found this aspect to be refreshing and pleasing.
* Funny enough to being one of Ashton Darrow's best friends, Gabriel even bears some psychical resemblances to him.
* Gabriel's route has the most secret images take place in the Carter Corp building.
	+ He also happens to have the least amount of secret scenes from both of his seasons too, with 8 in season 1 and 16 in season 2.
* Gabriel's female counterpart can be considered to be Lisa Parker, as the two are actually quite similar in some ways.
	+ Which is ironic since the two are barley ever seen interacting.
		- Both work at Carter Corp.
		- Both have a history of being a serial romanticist but with many failed relationships as well.
		- Both are a little promiscuous, like to tease the player and are confident but are overall calm and poised and often give the player relationship advice.
		- Both have issues with their father and don't get along with them.
		- Both have fair skin and have the same shade of blonde hair.
		- The two could possibly pass as siblings due to their close appearance similarities.
		- They both overall have some of the same personality traits.
	+ Lisa can be considered as the "good" version of Gabriel as she gets along with many people that Gabriel doesn't get along with even though she has some of his personality traits, especially with Matt Ortega.
	+ If the two were to ever try and date one day, the relationship could possible work out due to the things they have in common.
		- In Gabriel's route, Gabriel was notorious for sleeping with many of the female employees that worked at Carter Corp and being a womanizer, so the fact that he's never hit on Lisa in any of the routes is quite shocking since she's considered very attractive.
* Gabriel could possibly be right handed due to him wearing his watch on his left wrist.
* Gabriel's character has been over hated by fans in both his season 1 and season 2, having been received as lukewarm by the fandom given that his second season focused more on Matt and less on him. Many fans felt this route was the one where fans would rather end up with the second love interest by majority. Cassidy Sparke has been received as a cliché villainess and because of fans being unable to bear Gabriel's behavior sometimes, it made them hesitant to read the second season.
	+ Cassidy actually doesn't appear that much in Gabriel's season 2 as compared to season 1.
		- It is sometimes stated by fans in a joking manner and even in anger that Matt overshadowed Gabriel from start and hence the writers tried their best to show the positive of Matt while they showed the negative aspects of Gabriel. Some fans dub his second season as Matt Season 2 2.0 due to Matt being more prominently featured than Gabriel, and she can even end up with him and say she loves him in his ending.
* In Jake's route, improvements on his character were made and he was well received in that route.
* Gabriel has been scheduled to get a third season according to Is it Love net, some fans felt season 2 was the final but this was a misconception. His final season might take place in the Japanese branch of Carter Corp due to it ending on a cliffhanger.
* Gabriel might reprise his role as the male friend to Mark's main character like he did with Jake's as both Mark and Gabriel have more interactions as frenemies and that he is the only male that Gabriel has shared a lot of screen time with excluding Matt Ortega.
	+ This theory has been debunked as the player did not have a male best friend.
* Gabriel is the only main love interest to be involved in two rivalries at the same time. The one between Mark and him and the other being Matt and him seen in almost every route.
	+ Gabriel seems to like Mark more than Matt though.
* He can be considered as an underrated and misused characters by fans. Some fans even blame this because of Matt Ortega and the favoritism offered to him in both seasons.
* Gabriel and Adam Peterson can be the source through which another love interest William Sheffield from Blue Swan was based on in terms of appearance.
* He has been joked by fans to be the father of the player's child from Ryan's route due to the kid having blond hair. Cassidy Sparke mentioned this too when she confronted the player about it.
* He is one of the 6 love interests that has a book adaptation.
* Even though he has never been seen interacting with children that much, he is probably good with children since he babysits Jenny Blake's baby daughters, Laure & Anne Stewart.
* In Jarod's route, one of the boy scouts who suffers a dislocated shoulder shares his forename Gabriel.
* He is the sixth male character to suffer a naked glitch after Mark Leviels, Jake Stewart, Haku Kobayashi, Chuck Stanford and William Sheffield.
* In his season 1 bad ending image, rather than wearing a dark purple suit, he is wearing a grey suit and purple tie, this is obviously an oversight from the artists.