Gwendolyn Sherwood/Relationships

Character
Gallery
**Relationships**
Outfits
Quotes

* The Roseweld Family
* The Rabbot Brigade
* The Wakeman Family
* The Carbunkle Family
* The Sherwood Family

Katherine Milton
Gwendolyn is quite close to her adoptive mother Katherine, the head matriarch of the Roseweld family. Katherine is a strong and confident woman who is always supportive and encouraging of Gwendolyn's decisions, let alone a sweet and generous mother that doesn't rais her voice at anyone, unless if needed.

Gretchen Milton
Gwendolyn has an excellent relationship with her adoptive mother's mother, Gretchen. They are often seen going shopping together, playing games, and attending events as an aunt/middle daughter combination. While Gwendolyn looks up to Gretchen’s adventurous and fun-loving nature, Gretchen also gives Gwendolyn a lot of advice when needed.

Glacier the Hedgehog
Glacier, Gwendolyn’s adoptive step-aunt, has a strong bond with her oldest niece. She is affectionate and caring, and always looks out for Gwendolyn’s best interests. Gwendolyn loves spending time with Glacier, and values the wisdom she shares with her.

Blizzard the Hedgehog
Gwendolyn has a good relationship with her adoptive fatherly figure (now father, as of Katherine Gets Married!), Blizzard. While Gwendolyn sometimes acts without considering the consequences of her actions, Blizzard is able to provide a calm and collected voice of reason.

Blitz the Chao
Blitz is Gwendolyn’s older cousin of the family and happens to be his girlfriend, and the two share an exceptional bond. Gwendolyn and Blitz are frequently seen helping each other out and confiding in one another, and for fun, she calls him "Jell-O shot", due to him being red, and also calls him her "sweet baboo", due to her loving him a lot as his girlfriend.

Penelope Atchison
Gwendolyn is close friends with Penelope, the oldest daughter of Rachel Atchison. She often confides in Penelope, knowing that her friend will always listen and offer her advice.

Zooey Fitzpatrick
Gwendolyn and Zooey have been friends and best siblings since they were small when they were first adopted by Katherine. Zooey is always willing to help out Gwendolyn when she's in need, and Gwendolyn trusts Zooey with her deepest and darkest secrets.

Amelia Wilberson
Amelia is Gwendolyn's youngest adopted sister and friend. When they first met, they weren’t the best of friends, but over time they formed a strong bond. Amelia is a great source of comfort and understanding, being able to sympathize with Gwendolyn's struggles and help her to face them with courage.

Kate Anderson
Kate is Gwendolyn's little friend on her friend’s side of the family. Kate is a fun and supportive person who always puts Gwendolyn first. She is always understanding of Gwendolyn's needs and is always willing to lend an ear or provide some words of wisdom for her.
Mandy Maynard
Gwendolyn and Mandy are close friends and strong-bonded adopted sisters. They typically get along like sisters, and are always there for one another. Mandy has become a dependable person in Gwendolyn’s life, which makes their friendship all the more meaningful.

Maxine Atwood
Maxine and Gwendolyn are good friends and adopted siblings. They frequently share fun and endearing memories together, and Gwendolyn always values Maxine’s witty insights and general quirky nature.

Kamiko Yokoyama
Kamiko is one of Gwendolyn’s closest friends and adopted sister overall. She values Gwendolyn’s honesty and trustworthiness, and knows that Gwendolyn will always be there for her.

Addison Schneider
Addison is Gwendolyn's friend within the Rabbot Brigade and adoptive sister, let alone a valuable member of the crew. She's always supportive of Gwendolyn, and is always willing to offer help when required. Addison is a great friend who can make Gwendolyn laugh, and is always willing to listen when Gwendolyn needs to talk.

Samantha Hopkinson
Samantha is Gwendolyn's best friend and smartest adopted sibling since her inception, when she was originally a robot that looked like a table. The two have been through everything together and share a very strong bond of friendship. Gwendolyn loves spending time with Samantha, and they often find themselves at the Roseweld family estate together, where they can explore and have fun.

Allison Vineyard
Allison is Gwendolyn's closest friend within the Roseweld family. Gwendolyn first met Allison when she was invited to a family dinner way back when she was a crudely made robot, and they hit it off right away. The two are close, with Allison typically looking out for Gwendolyn and offering her advice.

Kaitelynne Dougherty
Gwendolyn and Kaitelynnehave grown close, thanks in part to their shared love of adventure and exploration. Despite being the same age between the two of them, Gwendolyn and Kaitelynne hit it off right away. With Kaitelynne being the same age as Gwendolyn, she is often highly-reliant on her middle sister for moral support and guidance in her life. This is something Gwendolyn is constantly providing, despite the fact that the two of them go on many wild outings and adventures together. The two of them can regularly be seen pulling out their gear on any given weekend and heading to unknown places full of intrigue and mystery.

Isabella Callahan
The relationship between Gwendolyn and her younger adopted sister, Isabella, has had its ups and downs, ever since Isabella's inception when she was built by Katherine. Their relationship grew from a bond of tween and teenage rivalry and mischief to one of deep friendship. The two of them frequently reached out to one another for support and comfort when needed. Gwendolyn has been especially supportive and protective of Isabella, despite their minor spats growing up. Despite this, firecracker nature and optimistic attitude quickly stole Gwendolyn's heart, and the pair were practically inseparable. They were two of a kind, both with goofy personalities and an endless ambition to explore and create. Gwendolyn was often drawn to Gwendolyn's fearless outlook on life, while Gwendolyn was inspired by Gwendolyn's depth and determination. Despite the age difference, the two are constantly pushing each other to follow their dreams and explore their passions.

Andrea Hatfield
The relationship between her and Andrea had a bit of a rather very rocky start, due to their initial lack of connection. Even though the two of them quickly became friends and shared interests when they were adopted firsthand, there were still times when tension was high. Over time, though, Gwendolyn and Andrea have realized that their vastly different personalities don’t have to be a hindrance and have instead become a source of strength and understanding. They even openly admit that they learn a lot from each other, whether it be in the classroom or out in the world.
Jenny Wakeman
Gwendolyn and Jenny have been friends since Gwendolyn was very young and when Gwendolyn was still a robotic hedgehog. They often have silly adventures together, and Gwendolyn trusts Jenny with her deepest secrets. The two are practically inseparable and are typically seen goofing around and having fun.

Nora Wakeman
Nora has been a friend and relative of the Roseweld family since Gwendolyn was nothing more than a ripoff of herself. She has been a strong supporter of Gwendolyn, typically encouraging her to go on adventures with Jenny and welcoming her into her home dimension. She has also been understanding and supportive of some difficulties Gwendolyn has had, such as when she was a ripoff of her own self.

Glenn Wakeman
Glenn and Gwendolyn have been close since Gwendolyn was a young little child. Glenn frequently visits Gwendolyn's home via dimension hopping, and the two have conversations about life, family, and their relationships of their families together. Likewise, Glenn does his best to listen to Gwendolyn and give her sound advice, which she greatly appreciates.
Brad Carbunkle
Brad and Gwendolyn have been friends since Gwendolyn started dimension hopping when Gwendolyn was still a robotic hedgehog years ago. They have shared many adventures together and often talk about their hopes and dreams. Brad is a good listener and often offers advice to Gwendolyn when she's going through a hard time.

Tuck Carbunkle
The two may not get along very well due to their differences, but Tuck does see her as a big sisterly figure.
Molly Sherwood
Molly and Gwendolyn have a strong and loving relationship as mother and oldest daughter, and Gwendolyn is typically found snuggled up in Molly's ample arms, and sometimes, on her ample bust. Gwendolyn had an unusually close relationship with Molly Sherwood, Gwendolyn, and Melody’s mother. Molly is a very large woman, weighing a little over four-hundred pounds, which caused her to occasionally get stuck in door frames at some times. As a joke, Gwendolyn found a way to include her weight into her nickname for her and affectionately called her “Molly Sherwood the Flabbit”.
However, despite her immense size, Molly never wanted to be defined by it and that’s where Gwendolyn stepped in. Gwendolyn had a very real and loving relationship with Molly, and the two enjoyed many evenings of laughter and frivolity together. Molly was a huge source of comfort and kindness that Gwendolyn had never had before, and even though she was technically an adult, Gwendolyn saw her as a role model and a source of moral guidance.
According to Gwendolyn, Molly is a very nurturing person as well, which could often be seen when it came to her daughters, Gwendolyn and Melody. Molly appreciated the way Gwendolyn looked out for them and never wanted to do anything to make Gwendolyn uncomfortable or leave her out. Gwendolyn saw this and, in turn, developed a great respect and fondness for Molly. The two shared a lot of the same values and beliefs, which helped build a strong bond between the two.
The relationship between Molly and Gwendolyn is best described with major parent qualities. Molly treated Gwendolyn with respect and understanding, which was something Gwendolyn had been missing in her life before. Even when Molly would scold Gwendolyn and Melody, she would do it in such a loving and gentle way as if she were talking to a family member.
Molly showed Gwendolyn the same level of respect and appreciation in return. She would often inquire about what was going on in Gwendolyn's life, sharing both stories of joy and stories of difficulty, although she would usually end with a positive message or a life lesson. Molly was also very helpful when it came to giving dating and life advice. Throughout their time together, Molly helped Gwendolyn learn many valuable skills, such as how to handle relationships, boundaries, decision-making, and emotional intelligence.

Melody Sherwood
She and Melody, who have an age difference of only 3 years, have a high level of respect for each other and Melody frequently mimics her big friend. Melody’s loyalty and admiration to Gwendolyn have also inspired her to bake for charity. Melody has used her baking skills as an avenue for gratitude and has baked countless batches of delicious confectionary goods for those who require the extra lift. Each treat is carefully crafted with love and care, and with a little note from Melody and from Gwendolyn’s inspiration.
As can be expected, Gwendolyn is greatly touched by this gesture, and even more so when she discovers that the movement and the motivation behind it all were inspired by her. For Gwendolyn, this gesture and the friendship formed between them are truly a reminder that as long as one puts in the effort, together they can accomplish so much more.
This is precisely the kind of friendship that Gwendolyn and Melody share. No matter where they are, they know that together they can make a difference.

Dorothy Sherwood
She's Gwendolyn and Melody's aunt who weighs in at a whopping 500 pounds, making her the largest woman in the Sherwood family overall. She is a kind, caring woman who is always eager to please. Gwendolyn has a good relationship with her, mostly because of her own large size and eagerness to please. She often helps out with the family's daily affairs, and is always amused by Gwendolyn's jokes. Gwendolyn and Dorothy have a very close friendship bond due to their mutual affront to 'skinny-shaming' and other forms of size-based discrimination. Dorothy's deep understanding and love for Gwendolyn helped her learn to love herself more, while Gwendolyn enjoyed just having someone to talk to who understood her struggles.
Overall, Gwendolyn has a complicated yet nurturing relationship with the Sherwood family. While her relationship with Trevor remains distant and strained, the strong bonds she has with Molly, Melody, and Dorothy make up for it. She is always greeted with open arms by the Sherwood family, and they are always willing to help her in any way they can. On the plus side, Gwendolyn has been in close contact with all three of them since she was a young child, as their families were all close. They've all been through good and bad times together, but through it all the relationship between them has remained strong. She, Dorothy, Melody, Molly, and Gwendolyn have a very solid relationship, and Gwendolyn has gotten to experience all sorts of things with them.
Dorothy and Gwendolyn appear in many episodes featuring Gwendolyn, sometimes as antagonists, sometimes as allies. Of all three characters, Gwendolyn seems to get along the best with Dorothy, since Dorothy gives her the same down-to-earth advice and support she gives Gwendolyn. Gwendolyn has had her fair share of arguments with Dorothy over the years before being adopted, though. Sometimes, it's always ending up with Gwendolyn screaming things like “Get off, Dorothy!”, while Dorothy sits on Gwendolyni with her immense size, but they resolve their differences and remain close.
When it comes to Gwendolyn, and Melody's aunt, Dorothy, Gwendolyn and her are also on good terms. Gwendolyn admires her immense strength, wisdom, and courage and has realized what an amazing woman she is. Dorothy tends to give Gwendolyn similar advice that she gives Gwendolyn, which can get annoying at times, but it's been proven to be helpful and Gwendolyn respects her for it.
When times are tough for the trio, Gwendolyn's usually the first to come to the rescue and make sure everyone's okay. She's always known to come up with practical solutions to help solve problems, and can tell when one of her friends is really in trouble. Even when Dorothy's not around, Gwendolyn's still willing to look after Gwendolyn as if she were her own family, showing how strong their relationship really is.

Trevor Needell
Trevor Needell, Gwendolyn's divorced father, is the least liked and involved in their family. He is frequently absent and rarely interacts with the family, especially not Gwendolyn. He dislikes her greeting him with her usual large smile and always has a scowl ready for her when she visits. As a result, Gwendolyn keeps her distance and does not interact with him much.
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