Chuck Bass

**Charles Bartholomew "Chuck" Bass** is a main character in the *Gossip Girl*. He is portrayed by Ed Westwick.

Throughout the television series, Chuck has an on-again/off-again relationship with Blair Waldorf. They marry in the series finale.

He is best friends with Nate Archibald. He is also good friends with Serena van der Woodsen, Ryan Blanchard and Dan Humphrey. Chuck appeared in 117 episodes.

## Summary

Chuck Bass was born on January 19, 1991 and grew up as the only child of Bartholomew "Bart" Bass, a self-made billionaire who owns the New York Palace Hotel. Chuck is generally shown throughout the first two seasons as the group's bad boy, and is frequently manipulative. However, a softer side to his personality is formed more for people cares about as the series progresses, most notably Nate and Blair. He often blames himself for his mother's death even though it isn't his fault, and he has a tendency to not completely trust people and is always in search of ways to succeed.

Chuck is orphaned in his senior year at high school due to the death of his father in a car accident, before being adopted by Lily van der Woodsen, his stepmother, and the only parent who Chuck really connected to and loved unconditionally.

## Television Series

### Season One

Chuck makes his first appearance in Pilot at Eleanor Waldorf's party. At the bar inside the Palace, he tries to flirt with and kiss Serena but she rejects him. At Blair's Kiss on the Lips party, he meets Jenny Humphrey and attempts to rape her. However, he is stopped by Dan Humphrey, who punches him. At Bart's annual brunch, he is told by his father that he needs to meet new people and find something to be apart of. He also outs Serena for sleeping with Nate (The Wild Brunch). Chuck's loyalty to Nate Archibald is shown when he stops him from being taken advantage of by Carter Baizen after a Lost Weekend gone wrong (Bad News Blair). On a constant search to gain Bart's approval, Chuck explores the option for Bass Industries to acquire the club Victrola. However, Bart is not pleased with Chuck's idea and refuses to help at first, but then decides to take a second look. Nate and Blair break up, and she goes to see Chuck at Victrola to escape emotionally dealing with it. While there, she does a strip dance routine onstage which entrances Chuck. While taking her home, they have sex causing Blair to lose her virginity to him (Victor Victrola). While at her birthday party soon after, Chuck admits to having feelings for her, which she initially rejects but ultimately gives in to (Seventeen Candles). Nate admits to Chuck later that seeing Blair happier after their breakup is causing him to miss her. Jealous and still hooking up with her from time to time, Chuck schemes to keep them apart. He gets Nate kicked out of Cotillion by manipulating him into punching Carter. But Blair realizes Chuck was behind the whole thing and ends their affair and gets back together with Nate. Afterwards, a heartbroken Chuck leaves the city (Hi, Society). After running into Bart, Blair discovers Chuck is in Monaco and begs him not to tell Nate about their sleeping together. He leaves her messages unanswered until Christmas morning, when he texts Blair a photo of him with Nate asking who he would tell (Roman Holiday).

At a pool party hosted by Serena, Chuck tells Blair that he's going to hold their sleeping together over Blair's head until he gets bored. As a result, Blair tries to distance herself from Nate, who seems to want to get closer to her. Later, the two argue and the whole thing is caught on tape by Vanessa Abrams, who is filming a documentary project. Chuck gives her ten thousand dollars, which she uses to create a charity for kids with genital herpes in his name. She gives the tape to Blair, who in turn pays her rent for a year. Also, Bart and Lily officially get engaged. (School Lies). When Blair thinks she's pregnant, Serena, thinking Blair only slept with Chuck, asks him for help getting her to take a test. When he confronts her about it, she says she has pushed whatever happened between them out of her mind. Angry, Chuck tips off Gossip Girl that Blair slept with both him and Nate in the same week. Blair's reputation is quickly ruined, as is his friendship with Nate. Nate assumes it's a lie until Jenny, who is sick of being looked over by Blair, confirms it. The two fight outside school and Nate tells Chuck to stay away from him, then breaks up with Blair. Feeling alone, Blair goes to see Chuck and tells him that his plan worked and he's the only one she can turn to. He informs her that she doesn't have him anymore, as she holds no more fascination for him anymore (A Thin Line Between Chuck and Nate).

During Spring Break, the Bass' and van der Woodsen's move in together. Chuck is particularly annoying to Serena, as he invades her personal space often and smokes marijuana in her bathroom, and becomes close with Eric van der Woodsen, whom he forms a brotherly relationship with. While having a tasting for wedding food, Serena receives a package that contains pornography and handcuffs. Everyone thinks Chuck sent it, though he ultimately denies it. As a result, Bart makes Chuck his best man but only if he behaves himself. Soon after, champagne in Serena's name is sent to Constance/St. Jude's and Chuck is blamed for that as well. Finally, Serena receives a bag of cocaine and at this point is past her breaking point. She informs Bart of what Chuck has been doing, who kicks Bart out of the family suite. However, it's later revealed that the presents were in fact not sent by Chuck, but by Georgina Sparks, one of Serena's old "friends" (The Blair Bitch Project). Upon her return, Georgina tries to get Serena to hang out with her and go back to their old partying ways. Serena has no interest in returning to that life, but is drugged by Georgina when she says no. She misses the SATs, but Chuck pays someone to take the test for her, as he also paid for someone to take the test for himself (Desperately Seeking Serena). After a downward spiral, Serena admits to Chuck, Nate, and Blair that Georgina is blackmailing her with a sex tape gone wrong that shows a friend of theirs dying on Serena's watch. Chuck reveals he lost his virginity to Georgina in the sixth grade, although he clarifies that he has been avoiding her ever since. At Bart and Lily's rehearsal dinner, he leaves with Blair to find Georgina and take her down for good (Woman on the Verge). Unable to find her, him and Blair stay up most of the night at her apartment and make a new plan instead. He writes his best man speech at the last minute. At the wedding, he sees Howard Archibald participate in a sketchy deal and informs Nate, who catches his father trying to leave town to avoid going to prison. They make up, and Chuck admits he loves Blair. Nate realizes Chuck really means it and decides not to stand in their way. During his speech, he gets inspired to speak from his heart and forgoes his note cards. In the speech, he talks of true love and the power of forgiveness and perseverance, inspired by his relationship with Blair. After, she forgives him for revealing she slept with Nate and the two enter into a relationship. He suggests they take it slow, and Blair finally believes that Chuck is a romantic at heart. Once Bart hears of their relationship, he is pleased and hopes Chuck will use it as a way to mature and abandon his childish ways. After hearing his father speak about how being committed will change him, Chuck is spooked and decides not to accompany Blair to Europe, as originally planned. Instead of meeting her, he seduces the Bass' new interior designer. Blair leaves for Europe believing Chuck will meet her there (Much 'I Do' About Nothing).

### Season Two

In the season two premiere Summer Kind of Wonderful, we learn Blair has stayed in Europe over the summer while being angry at Chuck for abandoning her. Because of his fear of commitment, Chuck has stayed in the Hamptons trying to get over Blair by sleeping with a different girl every day. When she returns, he realizes that he regrets his actions; however, it is too late, Blair has begun a relationship with Marcus Beaton, a British Lord whom she met while in Europe. At the Vitamin Water White Party, while Blair is waiting for Marcus to pick her up, Chuck reveals that he was afraid that if they spent the entire summer together, she might see who he really is. Blair then says that she will belong to him and him only, if he tells her he loves her. He ultimately can't expose himself in that way and Blair leaves with Marcus. Chuck begins to have sexual performance problems due to being rejected by Blair, and eventually asks her to have sex with him; which she initially refuses. During a blackout, the two end up kissing while he pretends to be Marcus (The Dark Night). Dan, on a snooping writing assignment, pretends to become close to Chuck and he reveals that his mother died in childbirth and he feels responsible for her death. After he discovers Dan was writing about him, he lies that his mother died in a plane crash. A guilt ridden Dan sends what he wrote to Bart, who admits to Chuck that he never blamed him for his mother's death and he has trouble being close to him because he sees her in Chuck (The Serena Also Rises). While visit Yale University, Chuck is kidnapped by a secret society who offer to let him in if he gives them Nate, who they hate because of losing money due to Howard Archibald. However, Chuck decides not to and sets up Dan instead. When Nate finds out, he ends his friendship with Chuck and begins to befriend Dan (New Haven Can Wait). In Chuck In Real Life, Blair makes a deal with Chuck to seduce Vanessa to humiliate her, but he decides to help her for real. Bart finds out that Chuck was planning to buy the bar she wants to save, and tells him again that he is a disappointment. Meanwhile, Blair sees that Chuck is willing to help Vanessa and ends the deal; meaning he won and can have sex with her. Before they can, he asks her to tell him she loves him. When she can't, he leaves. After Bart's death (It's a Wonderful Lie), Chuck begins a downward spiral and ends up buying Lily's biggest secret from his PI Andrew Tyler. Saddened at how Chuck is behaving, Blair finally tells him she loves him but he rejects her. He eventually comes around and after she calms him down, he leaves her a note saying he's leaving because she deserves better (O Brother, Where Bart Thou?). Chuck's uncle Jack Bass brings him back to New York (In the Realm of the Basses), and Bart's will is read. It's revealed that he left Chuck the majority of shares in Bass Industries. Angry, Jack sets Chuck up to show the board that he isn't suited for the job and he succeeds (Gone with the Will). Wanting to get Jack out for good, Chuck teams up with Lily to get rid of him. They are unsuccessful until Lily has the idea to finish her and Bart's original plans and adopt Chuck; thus becoming his legal guardian and able to take over the company. While high on cocaine, Jack attempts to rape Lily but is stopped by Chuck in time. Afterwards, he decides to move back into the VDW's penthouse (You've Got Yale!). Meanwhile, Blair and Nate get back together (Remains of the J), causing Chuck to retaliate by sleeping with Vanessa. When Serena begins dating a con artist, Gabriel Edwards, he teams up with Blair to fix things. This causes Nate to become jealous and confront Chuck about his proximity to Blair, and tells him to either make it work with her or let her go (Southern Gentlemen Prefer Blondes). While on a mission to catch Poppy Lifton, the real con artist, Blair asks Chuck to reveal her true feelings for her. Feeling he can't make her happy, he tells her that she was just a game to him, and she cries and walks away. Soon after, he sabotages her prom plans to follow the Prom Scrapbook she made as a child, making sure she has the perfect night. He also votes for her about a hundred times to make sure she wins prom queen (Valley Girls). In the season finale The Goodbye Gossip Girl, Gossip Girl puts a hit on everyone and it's revealed he slept with Vanessa and that Blair slept with Jack. Hurt, Chuck tells her that the hurt and lies are for nothing now and runs away to Europe. A week later, he returns and tracks Blair down. He admits that she caught up with him everywhere, and that he brought her gifts from all her favorite places in Europe. Finally, he tells her he loves her too and they passionately kiss, entering a relationship.

### Season Three

When season three returns with Reversals of Fortune, Chuck and Blair are happy and very much in love. They are not a traditional couple, and play a game all summer. Chuck seduces a girl at random and, before anything can actually happen, Blair appears, plays the "scorned woman" and humiliates the girl. They do this in order to ensure that their relationship stays exciting. Blair was very content with this game, until Serena causes her to question it. Blair tells Chuck she no longer wishes to play this game, and Chuck easily complies telling her that he only wants her to be happy. Chuck begins to be immersed in his work, including not spending a lot of time with Blair. Wanting to buy a hotel club from Sean McPherson, Chuck is told to buy a particular photo up for auction at the Sotheby's auction. However, Blair is also wanting the photo to secure a position with a society club. Serena ultimately wins the photo, and gives it to Blair. Wanting Chuck to succeed, she gives it to him. However, they deduce that Georgina set it up and he ends his interest in schmoozing McPherson. He decides to think bigger and cashes out all of his shares of Bass Industries to purchase The Empire Hotel (The Lost Boy). After Blair's failures to conquer NYU, he confronts her and tells her that she was able to make him an honest man and is someone special. He also sets her up with a paparazzi to make her feel good (Dan de Fleurette). In Enough About Eve, wanting to give the Freshman Toast at The NYU Parent's Dinner, Blair sets Chuck up to kiss Josh Ellis in exchange for being able to. His plans get canceled, so he shows up at the dinner and gets a little too much info from one of Blair's new minions. Then he sees Blair and the man he kissed talking and laughing and he realizes something is definitely up. Blair's plan is revealed when Vanessa hides a microphone in her purse, and her nasty rant about Vanessa is aired to the entire audience, including how she used Chuck to get the speech. Blair goes over to Chuck's to apologize but he needs time to think about it. When it's time for his club to open, he leaves Blair out of the planning due to still feeling like he can't trust her. She has Jack send over a liquor license to help but eventually finds out it was a fake. She tells Chuck, who already figured out, and they use it to their advantage to garner maximum press (How to Succeed in Bassness).

In The Debarted it is the anniversary of Bart's death and Chuck wrestles with the dilemma of following his conscience or that of his father. All day he is very agitated with everyone, especially Blair who wants to comfort him and thinks he should visit his father's grave. He even has visions of his father, who berates Chuck for being soft and not having the keen business sense that he has. When on the way to a big business meeting, he learns that Serena has been in a car accident. He turns his limo around and goes to the hospital much to his father's ghost's dismay, and he finally blows up, causing the ghost vanishes. When he enters the hospital, he is overcome with emotion and is reminded of when he came to see his father right before his death. Blair finds him sitting in the hospital floor. She tells him that everyone is there and comforts him, telling him that he has become a man in ways that his father never was and pulls him back up. Later, while visiting his father's grave he sees a mystery woman lying yellow roses, his father's favorite flower, on his gave. She also drops a locket, engraved with the letter *E.* In The Hurt Locket**,** Chuck learns that the woman's name is Elizabeth Fisher and she may be his mother. He spends a lot of time and resources, including using his private investigator to find out who she is, and bribes several hotel employees to get more information about her. She eventually reveals that she is his mother, and after a brief falling out when Chuck believes she just wants his money, they become very close (The Lady Vanished). In The Sixteen Year Old Virgin, Chuck is slapped with a sexual harassment lawsuits involving employees from The Palace Hotel. At the same time, Jack arrives in town. Chuck worries that his mother will think less of him as a result of the slander, but she is supportive. When he invites her to a benefit for his father, she declines due to fears of running into his Jack. When he brings up Elizabeth when talking to Jack later, Jack tells Chuck that he was there when his mother was buried, and that she's playing him, causing Chuck to test the DNA on a glass she had drank from to find out for sure. When Chuck's lawyer tells Chuck that a Christian organization is planning a boycott against the Empire as a result of the sexual harassment lawsuits, he advises that Chuck sign over the company to a family member until things quiet down. Jack interrupts and nominates himself, but Chuck refuses him, as well as Lily, because he doesn't want it to seem that Bass Industries is bailing him out. When the DNA results come back positive, Chuck decides to sign over the hotel to his mother. It's revealed that Elizabeth, Jack, and the lawyer were working together to steal the hotel from Chuck. The next day, Chuck is removed from his penthouse and Elizabeth admits she signed the hotel over to Jack. In a last ditch attempt to save the hotel, he makes a plea to her, and she confesses that she is in love with Jack. Elizabeth, disgusted with what she has done, tells Chuck that she lied to him, and isn't his mother, and leaves New York for good, although a conversation with Jack before she leaves suggests that she really is Chuck's mother (The Empire Strikes Jack).

In the Inglourious Bassterds**,** Jack says he will give back the hotel to Chuck under one condition: he wants to have sex with Blair, so that Jack could have everything that Chuck has ever wanted. Jack follows Blair to a boutique and makes his offer. After Chuck makes it clear to her that Jack will never give back the Empire, and is going to sell it off to someone else, she decides that she has to sleep with Jack to save Chuck's hotel. Blair goes to Chuck's old suite to meet Jack, wearing the dress Jack sent her earlier, and tells him that her one condition is that he sign a contract stating that he will never tell Chuck what happened and that he will sell the Empire back to him so he's not suspicious. Jack kisses Blair, and then tells her that Chuck did know and that he knew that Blair would want to do whatever it takes to help him, and set her up. Hurt and disgusted, Blair cries and tells Chuck that she can't believe he would do this to him, but Chuck tells her that she was the one who cheated on him, despite the fact that he orchestrated it. She breaks up with him, and upon his return to his suite, he discovers the contract. Realizing how bad he messed up, he offers to throw a very pregnant Dorotea Kishlovsky and Vanya a wedding. While Blair really wants for them to get back together, she refuses because of the disgust she feels for still loving him even after the way he acted. She feels it is not right to go as far as she did to help a person, no matter how much you love them; considering what she did for Chuck, she couldn't live with herself if she stayed with him. After seeing how happy Dorota and Vanya are together, she ends the relationship for good and he decides to revert to bedding any woman who is willing to cope with the pain (The Unblairable Lightness of Being). After Lily is diagnosed with cancer (Dr. Estrangeloved), Chuck avoids seeing her, as he's afraid of losing her. However, he's convinced to see her after Blair tells him he shouldn't close his heart to Lily. After seeing her, he becomes suspicious at her diagnosis due to how healthy she looks. Blair is also accepted into Columbia University after Chuck applied for her, knowing she had too much pride to admit NYU was a mistake (It's a Dad, Dad, Dad, Dad World). He teams up with Jenny to discover what William van der Woodsen is hiding.After a long night, they figure out that Dr. van der Woodsen and Dr. Holland Campbell have been working together to make Lily believe that she has cancer in order for him to get closer to Lily and break her and Rufus up; the antibiotics mimic the symptoms of the cancer she is supposed to have. Later that evening, Chuck and Blair have to find some way to stall Holland, so they do what they do best: role play. Acting like a couple they spill out all their relationship issues, from Blair sleeping with Jack to Chuck selling Blair out for his hotel. But when Dan signals to them, they accuse her of prescribing medicine to Lily. When they return to the Van Der Woodsen's apartment to find William, he is gone. Chuck waits with Blair for Cameron, her new friend, to come pick her up and tells her that he will be waiting for her the next day at the top of the Empire State Building at 7:00 PM and if she isn't there by 7:01, he is closing his heart to her forever. In the season finale Last Tango, Then Paris, Blair spends the day trying to avoid meeting with Chuck, but ultimately decides to meet him and continue their relationship. But before she can go, Dorota goes into labor and Blair escorts her to the hospital. She ends up being too late, but finds the flowers Chuck left in a trashcan. At the same time, a devastated Chuck sleeps with Jenny wanting to quell the pain. Blair shows up after and confesses her love for him. They get back together, and both Blair and Chuck are over the moon. They decide to go see Dorota at the hospital and on their way in, he begins to propose to Blair. Halfway in, Dan interrupts to punch Chuck. It's revealed Chuck slept with Jenny, and Blair ends their relationship again. A week later, Chuck is seen wandering through an alley in Prague. He is mugged by two men. They find the engagement ring that was supposed to be Blair's, but Chuck does not want to give it up, telling them he has money to give and that he is rich, but he has to keep the ring. As he tries to take back the ring, Chuck is shot by one of the men. The last shot is of him left bleeding in the alleyway.

### Season Four

In the first episode Belles de Jour, it's revealed Chuck is alive and was reduced by a French woman named Eva Coupeau. Wanting to forget who he is, he creates a fake identity for himself named Henry Prince. Worried at the prospect of him being dead, Serena tracks him down and discovers he's going to abandon being Chuck Bass and sell everything, including The Empire and Bass Industries. On his way out of Paris, he is stopped by Blair who tells him that while she no longer loves him, she does care about him. He reveals his true identity to Eva and they head back for New York (Double Identity). After he returns to New York (The Undergraduates), he becomes kind and charitable thanks to Eva's influence. In Touch of Eva, a jealous Blair finds out Eva is a former escort and reveals it to Chuck. Having already been told by Nate, he isn't fazed. Blair then spots an envelope holding Chuck's passport and information, and places it inside Eva's suitcase to make it look like Eva knew who he was from the very beginning. Angry, he breaks up with Eva until he discovers Blair set them up. He begs Eva to take him back, but she refuses saying she knows he still has feelings for Blair. Chuck then declares war on Blair and sabotages various aspects of her life by making her lose a teacher assistantship (Goodbye, Columbia), and inviting Jenny back to town to spar with her (Easy J). After Jenny reveals to everyone she was banished due to sleeping with Chuck, they make a truce and agree not to fight. In War at the Roses, wanting to make it official, Nate and Serena have a contract drawn up. Dan, upset that Jenny can't return to the city for Rufus and Lily's first anniversary party, steals the contract and sets Blair up at her birthday party to be humiliated by a drunken video of her. She assumes Chuck leaked it until Dan comes forward. After the party, they announce to each other that they hate each other but end up having sex. This begins a sexual relationship between the two. After hooking up for awhile, they finally confess that they love each other. They kiss at his Saints and Sinners party, but Blair finds she will lose the chance to become the face of the Girl's Inc. foundation and Chuck will lose business on not being a bad boy anymore. They decide not to get back together, but that if it's meant to be, it will be (The Witches of Bushwick). Old Bass enemy Russell Thorpe and his daughter Raina come to New York, intending to destroy Bass Industries (The Kids Are Not Alright). Chuck begins dating Raina, and while their relationship begins as a business only sexual one, it eventually becomes something real. While on assignment for W Magazine, Blair discovers that Chuck's feelings for Raina are real and she's devastated. As a way to prove loyalty to him, Russell asks Chuck to kick Lily off the board of Bass Industries. He does, and the two engage in an argument in front of Raina, who considers family to be very important. She breaks up with him, angry at how little it means to him (It-Girl Happened One Night). He tries to win Raina back by using Nate as a wingman, but Raina ends up developing feelings for Nate instead (While You Weren't Sleeping). While throwing a party, Russell and Chuck have a confrontation and Russell reveals Bart killed his wife, Avery (Empire of the Son) in the fire he set to collect insurance money (as explained in Bonfire of the Vanity, in season two). After, he decides he misses Blair and wants her back, but she is ignoring his attempts. During a Modern Royalty photoshoot, he asks her old boss Epperly to find out. Epperly hires Blair and finds out she had a life changing kiss. Chuck eventually figures out she kissed Dan and sets him up to show Blair that he isn't a part of their world. This set up causes Blair, who was ready to finally be with Chuck too, to move on, citing that she knows Chuck isn't ready for a real relationship (The Kids Stay in the Picture). Meanwhile, Blair's prince Louis Grimaldi has arrived from Monaco to see her, and the two begin to date (Petty in Pink). In The Princesses and the Frog, Chuck finds out they might get engaged, he crashes the ball where Blair is being presented to Louis and drunkenly tells Louis' mother Sophie that he is the love of Blair's life. He is kicked out of the party, and Blair comes to see him at The Empire later, where she reveals Louis proposed. Angry, Chuck smashes a window pane and terrifies Blair into running away. The next day in Shattered Bass, Jack arrives in town, courtesy of Raina wanting to use him for revenge, and Blair goes to warn him. Jack meets with Russell, and agrees to help him get rid of Chuck. As part of their plan, he arrives at the site of Chuck's new hotel and has him taken away by nurses of a psychiatric hospital. He leaves the keycard for Russell to get into Chuck's suite. While he's there, Nate, Jack, and Chuck walk in and it's revealed the three of them were working together to get Russell. They discover Russell was stealing evidence from the night of the fire, and they decide to watch the tape. On it, they discover that Bart wasn't responsible for Avery's death; Russell was. Russell begs them not to tell Raina and offers to leave New York in exchange for silence. Chuck agrees, and tells Russell to leave and never return. He does, and it's all going well until Nate reveals to Raina that Russell killed her mother. She calls him in tears, and Russell assumes Chuck told her. Wanting revenge, he fakes a call to Blair that Chuck is about to jump off a building but when she arrives. He's waiting, ready to burn down Chuck's new hotel site with her in it. In The Wrong Goodbye, the episode picks up right after Russell has trapped Blair. She manages to secretly call Chuck so that he can hear what is going on and discover where she is. Chuck, Nate and Raina come to the hotel and Chuck rescues Blair from Russell. Raina confronts her father and Russell is subsequently arrested. After Blair is rescued, Chuck apologizes to her and offers to buy her a drink to calm her down. They end up at a bar mitzvah party and begin dancing. After awhile, they end up having sex. On the way back to the Constance party Louis is back, Blair admits that she will have to tell Louis that it's over. Chuck asks if she loves Louis, and Blair says she does, but not like she loves Chuck. She explains that with Louis, her love is lighter, more simple and makes her happy, but with Chuck it's intense and all-consuming. When they get to Constance, Chuck is surprised to find Louis still waiting. Louis says that he believes in Blair and knows she will figure it out and arrive. At that moment, Blair appears as Chuck left his jacket. She turns to Louis and says they need to talk, but Chuck interrupts and says the pair have his blessing and he is pleased they are getting married. Later, Blair finds Chuck and asks him why he did that. He explains that she deserves to be happy and says there is a difference between a great love and the right love. He points out that at the Empire State Building he didn't wait for Blair, but Louis waited for her all night. He asks how she feels about the night, and when Blair admits that she feels terrible, Chuck tells her that she is feeling guilty. He admits that he feels guilty too and suggests he is growing up. Blair says she didn't want to give Chuck up yet but he kisses her on the forehead and announces that she is the most powerful woman he knows. He says they need to let each other go and the pair tell each other that they will always love each other.

Some time later, at the VDW's, Blair is preparing to spend the summer with Louis in Monaco, but is civil when she says goodbye to Chuck. When Nate and Chuck return home, Nate sees that Chuck is really hurting over Blair and Chuck admits that Blair shines when she is with Louis, whereas he just brings out her dark side. He says she should be with Louis. Nate asks Chuck does he still love Blair and Chuck answers that he does. Nate is impressed that he is maturing and suggests that they spend a lost summer together.

### Season Five

After spending the summer traveling with Nate, the two end up in Los Angeles where Serena is working (Yes, Then Zero). While there, he gets into a motorcycle accident and discovers that he is unable to feel pain, or really anything. Upon returning to New York (Beauty and the Feast), he hires two men to beat him up in the hopes he can feel it. Dan discovers what he did, and researches ways to help him start to feel again. Meanwhile, Blair finds out she is pregnant but does not know who the father is. After taking a paternity test, she discovers it's Louis'. Right after, she goes to see Chuck at The Empire. He introduces her to his dog, Monkey, and she reveals her pregnancy. This news causes him to be able to feel again (The Jewel of Denial). He begins to see a therapist, who is able to convince him to let go of Blair by returning the engagement ring he bought for her (The Fasting and the Furious). However, it's revealed that Louis was paying Chuck's therapist to drive him into a rage to scare Blair away forever. He exposes this, which causes Blair to want time away from Louis. He goes to Blair's and apologizes for everything he did wrong in the years that they have known each other, and he's going to take care of himself from now on (I Am Number Nine).

As she's trying to pull Louis from the dark place he has been as a result of his jealousy of Chuck, Blair spends a day with Chuck to see if Chuck really has become a good person. As they are in therapy, Chuck tells Blair that he returned the engagement ring to Harry Winston. Chuck later tells her that she was the lightest thing that ever came into his life and that he just wants Blair to be happy, although he wishes that she could be happy with him (Rhodes to Perdition). In Riding in Town Cars with Boys, Blair asks Chuck if he would consider being a father to her baby, but wanting her to be happy, tells her to stay with Louis. After seeing how upset this makes her, Dan sets up a secret room at Ivy (as Charlie Rhodes)'s party to allow them to be together. In the room, Chuck says he only said what he said to not be selfish and that he wants her back. The paparazzi show up and they quickly depart in a car, inside which they decide to get back together and make plans to run away, but get into a serious car accident.

After a slight time jump, Chuck admits to Louis that Blair has cut him out of her life and he doesn't know why. Meanwhile, Blair tells Serena that in a desperate move to save Chuck's life after the accident, she made a deal with God to keep her vow to marry Louis if he can live (The End of the Affair?). In G.G., it's Blair's wedding day and Chuck plans to stay away until Eleanor comes to see him. She tells him that she knows he is the one for Blair and asks him to stop the wedding. When he arrives, Blair confesses that she loves him more and more everyday. Georgina catches their conversation on tape and it ends up on Gossip Girl, and plays during the ceremony. Blair flees and confronts Chuck, who tells her that Serena told him about her pact with God and that while he didn't send the tape, they can be together. She decides to marry Louis anyway, but at the reception, learns she made a terrible mistake when he reveals he doesn't love her anymore. When Blair turns up missing from the reception after leaving with Dan in The Backup Dan, Chuck teams up with Serena to find her. They eventually do, at an airport hotel. Sophie also tracks Blair down, and threatens her with the dowry in the prenup; which is so much money it will bankrupt the Waldorf's. Chuck offers to pay it to they can be together, but Blair tells him she wants to fix it on her own. She leaves for her honeymoon with Louis. After he finds out Dan sent the video (Cross Rhodes), he attempts to tell Blair at CeCe Rhodes' wake, but instead learns that Blair has feelings for Dan and doesn't care that he released the video. He also discovers that after the car accident, he needed a blood transfusion and Jack provided it (The Princess Dowry). Wanting to thank him, he invites Jack back to town where he is planning to open a hospital wing in his honor. While planning the event, he discovers that Jack has Hepatitis C and cannot donate blood. He figures Elizabeth donated the blood, and intends to thank her (Con-Heir). However, Andrew Tyler finds out Elizabeth was in a monastery as the time and couldn't have given Chuck the blood. Chuck instructs him to keep looking, as he wants to know. Meanwhile, Blair's divorce papers have come and she finds out Chuck paid her dowry. She confronts him about it, saying that he only did it to buy her back, but Chuck says he only wanted her to be free (It-Girl Interrupted). In Salon of the Dead, Chuck finds out that Diana Payne is his mother, but Nate emails Elizabeth and asks her for clarification. When she replies, she attaches a photo of herself pregnant with Chuck and a man's arm wrapped around her. Chuck recognizes the tattoo and wonders if Elizabeth is his mother and Jack is his father, not Bart (Despicable B).

In Raiders of the Lost Art he convinces Blair to help him find out what Diana hiding and how it links with Jack, and Nate, Lola, and Serena also join. They're able to crack her code and end up a brothel (the same brothel Chuck mistakenly attended in Carrnal Knowledge in season two). While there, Chuck discovers that Bart is alive. In The Fugitives, Bart explains that he faked his death to protect Chuck and Lily from a Bass competitor. Wanting to save his father, Chuck and the gang prepare a scheme to blackmail the competitor out of hurting Bart. After a series of mishaps, it's revealed that Andrew Tyler was in on it and turned on Bart to protect himself. He is arrested, and Bart becomes free to come out of hiding. Meanwhile, Gossip Girl begins to post excerpts from Blair's diary; in which she asks herself what to do if she never loves anyone the way she loves Chuck.

In the season finale The Return of the Ring, Blair goes to see Chuck at the Empire after an excerpt where she calls him a monster is released. He tells her that the blast doesn't matter, because it was a year ago, and that they have been through so much since then and made amends. Chuck asks her if she is still with Dan, and when he finds out that she is, he tells her that he's tired of this game and that he needs to move on. Later, Bart is questioning Chuck about his relationship with Blair. He says that he made a lot of mistakes when Bart left, including ruining things with Blair. Bart encourages Chuck to win Blair back and gives him the engagement ring that Chuck returned. At a press conference, Bart announces that he is cutting Chuck out of the company. After a confrontation, Bart stands by his decision and leaves Chuck on the roof. Right after, Blair comes and tells him that she wants to be with him and not Dan. He decides not to get back with her, not wanting to be in her shadow. At the end of the episode, Chuck goes to Monte Carlo with Jack to try and garner enough money to buy their way back into the Bass Industries game. While at a casino, Blair shows up and tells Chuck that she's all in for making it work between them.

### Season Six

The season premiere Gone Maybe Gone begins with a flashback of Blair and Chuck having sex in Monte Carlo. It's also revealed that they made a deal where Chuck defeats Bart and Blair succeeds at Waldorf Designs, and then they can be together forever. It's also revealed that Blair has the engagement ring on a chain around her neck. Chuck brings Bart's former translator Amira to Manhattan in the hopes of rattling Bart, who pays her ten million dollars to leave town. After Chuck discovers she and Bart had an affair, he takes her money and tells her she can't leave until she writes down everything she did with Bart, including locations and people. Bart fakes a text from Blair to distract Chuck and has Amira leave while he's gone. After she's left, she sends Chuck a letter telling her not to contact again and encloses a surveillance photo of herself and Bart entering a building with another man in a suit behind them (High Infidelity). After Blair becomes dehydrated and cannot plan her fashion show, Chuck takes over for her and his results please Blair highly. Afterwards he tracks down the man in the photo, who turns out to be Bart's former body guard. He pays the man to tell him that he drove Bart to a meeting with someone named Lady Alexander (Dirty Rotten Scandals). While trying to find her, Chuck and Blair discover Lady Alexander is a horse. They head to a horse show being held outside the city, where they discover Bart's friend is dead but his daughter Aman is there. Bart also shows up, and it's shown that Aman is very close to Bart; and even refers to him as uncle. Blair advises her to look into what Bart did to her childhood horse, and Aman decides to help Chuck. She comes to see Chuck later, and explains that her father was in the oil business. Chuck then figures out Bart's secret: that he was breaking federal law by conducting oil deals (Portrait of a Lady Alexander). With the help of Nate, Chuck figures out that the records for the oil deals are hidden behind a painting at the VDW's. However, that same painting Lily puts up for auction and ends up being sold to Ivy and Rufus. Chuck offers to buy it for twice what she paid for it, but is angry when he discovers that someone took the evidence before he acquired it (Where the Vile Things Are). Meanwhile in Save the Last Chance, Nate commits fraud by lying about how well The Spectator is and begins to be blackmailed by Bart. Ivy, wanting to destroy Lily, announces she stole the records and will give them to whoever ruins Lily's life first. Bart blackmails Nate into revealing Chuck's plan, and goes to see Ivy himself. Ivy reveals that she wants to take photos to pretend she slept with Bart to humiliate Lily but when he asks for the records, they've come up missing. It's revealed that Rufus took them from Ivy and gave them back to Lily. Chuck walks in on Bart and Ivy and receives a text from Dan, telling him Lily has the records. Chuck races to get them but gets there in time to see Lily burn them. He then tells Blair that he failed at his deal and can never be together. In It's Really Complicated, Blair brings Chuck out of his depression and the two search for a way to tie deaths related to the deal together. They successfully show Lily that Bart is a murderer, and a scared Lily leaves town for a spa. Over Chuck's games in The Revengers, Bart threatens Blair's safety and then tells Chuck that the only way to keep everyone he loves safe is to leave for Russia forever. Chuck and Blair have a emotional farewell, and Chuck gets on the plane. Later that night at Bart's party, it is revealed Chuck's plane crashed, and Chuck is presumed dead. Blair is devastated until Chuck arrives and announces to everyone that Bart tried to kill him. Afterwards, the two Bass men get into a fight on the roof which ends with Bart hanging off the side begging Chuck to save him. Wanting to end the struggle, Chuck and Blair allow Bart to fall to his death. In the series finale New York, I Love You XOXO, Blair and Chuck flee the scene and head to a bed and breakfast outside the city. The next day, Jack finds them and suggest they get married to obtain spousal privilege, since the cops are looking for them. Chuck finally proposes to Blair, and she immediately accepts. When they're in a court house trying to get married, Chuck says to Blair that he doesn't want to start their life this way and that they needs to be surrounded with the people they love. The wedding takes place in Bethesda Fountain in Central Park, with Serena, Nate, Jack, Dan, Eleanor, Cyrus, Lily, and Georgina in attendance. Meanwhile, two girls spot them and decide to call the police. While Cyrus is performing the ceremony, everybody hears a distant police siren. The do and end up marrying and kissing before the police arrive. When they do, they ask Chuck and Blair to come with them. Afterwards, they return to the Waldorf penthouse and explain that due to lack of evidence, Bart's death will be ruled as an accident. In the time jump, Blair is a success at Waldorf Designs and Chuck is assumed to continue being successful at Bass Industries. It's also shown that they have a son named Henry Bass.

## Appearance and Style

Chuck is described as being incredibly handsome in a men's aftershave commercial kind of way. Women, and even a few men, can hardly resist him. He has dark brown hair and dark chocolate eyes. His hair is always perfectly styled, his skin has a natural tan, and he is always well dressed, often wearing stylish, colorful, well-tailored suits. Chuck is acknowledged as a fashion icon for men's wear, and is known for wearing a lot of purple in his outfits. Throughout the first season, he's known for wearing a printed scarf everywhere.

## Personality

Chuck is very sleazy, self centered, and has a horny sense of humor. However, he is also shown to be very loyal to the select few he deems worthy, such as offering a loan for Nate and Anne Archibald and paying Blair's dowry. Throughout the first season he displayed a variety of near-sociopathic tendencies including attempted rape but in later seasons has matured into a respectable young adult. He is extravagant and often times throws around money but it seems to come from deeply rooted insecurities which were most likely instilled by his demanding father. He is also very witty and quick to verbally spar, showing that he is quite intelligent. His narcissism is apparent, often quoting **"**I'm Chuck Bass**"** after someone asks him a question on why he is deserving of such things (e.g Ivy League education).

## Relationships

### Family

* Blair Waldorf (Wife)
* Henry Bass (Son)
* Bartholomew "Bart" Bass (Father; deceased)
* Elizabeth Fisher/Evelyn Bass (Mother)
* Lillian "Lily" van der Woodsen (Adoptive mother/stepmother)
* Serena van der Woodsen (Adoptive sister/stepsister)
* Eric van der Woodsen (Adoptive brother/stepbrother)
* Dan Humphrey (Adoptive brother-in-law)
* Jack Bass (Uncle)
* Scott Rosson (adoptive half-brother/stepbrother)

### Romances

* Blair Waldorf Bass (Wife)
* Vanessa Abrams (One night stand)
* Jenny Humphrey (one night stand)
* Eva Coupeau (Ex-girlfriend)
* Raina Thorpe (Ex-girlfriend)

## Memorable Quotes

"I'm Chuck Bass." -On multiple occasions

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"Judge away. Shame turns me on."

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"Well, let's catch up. Take off our clothes. Stare at each other." -Pilot (1x1)

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"Don't mock the scarf, Nathaniel. It's my signature" -The Wild Brunch (1x2)

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"Look, Nathaniel, I care about three things: money, the pleasure money brings me, and you." -Dare Devil (1x5)

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"Let's take it slow this time. Do it right." -Chuck

"Chuck Bass is a romantic, who knew?" -Blair

"Now you do, and that's all that matters." -Much 'I Do' About Nothing (1x18)

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"I was a coward running away again. But everywhere I went, you caught up with me. So I had to come back." -The Goodbye Gossip Girl (2x25)

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" I am so sorry for the pain I've caused you. And I know I can't take it back, but I want to try and make it up to you. Even if it takes me the rest of my life." -Last Tango, Then Paris (3x22)

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"If two people are meant to be together, eventually they'll find their way back." -The Witches of Bushwick (4x9)

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"People like me don't write books. We're written about." -Yes, Then Zero (5x1)

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"I'm sorry for losing my temper the night you told me Louis proposed to you. I'm sorry for not waiting longer at the Empire State Building. I'm sorry for treating you like property. I'm sorry I didn't tell you I loved you when I knew I did. Most of all, I'm sorry I gave up on us and you never did." -I Am Number Nine (5x6)

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"Just because Louis is the father of your baby does not mean you should be with him,you should be with me. Because I'm going to love your baby as much I love you." -Riding in Town Cars With Boys (5x10)

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"I just wanted you to be free. Who you choose to love with that freedom is up to you." -It-Girl Interrupted (5x19)

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## Trivia

* His voicemail says "Leave me a message and I might listen to it."
* He lost his virginity in sixth grade to Georgina Sparks.
* He had a Latvian maid named Brigita.
* He is an atheist.
* He and Bart used to play squash when he was growing up.
* His dog, Monkey, was likely named as a tribute to his pet monkey in the novel series.
* He loves ice cream.
* In It Girl, Interrupted, Chuck mentioned that he spent a night with the Australian women's softball team resulted in a fractured rib and a tattoo of a kangaroo that he didn't know about for a month.