Jennifer 'Jenny' Humphrey
Jenny is the little sister of Dan and is a very innocent girl in the beginning. She tries to have Blair Waldorf as her friend and is used by Blair and her friends several times. But slowly Jenny begins to fight back and tries to be equal to Blair. She fails, when Blair finds out that Jenny's boyfriend Asher is gay and has a secret affair with Eric van der Woodsen, one of Jenny's friends. She is embarrassed and tries to be different from Blair, saying to her that she finally found out that she never wants to be anything like her. Jenny is also a very talented young designer and gets the chance of her life, when she gets an internship by Eleanor Waldorf.
While working there, the people and Eleanor herself get impressed by Jenny's designs. The young designer leaves school then to work full time. When Eleanor uses accidentally a dress from Jenny in one of her fashion shows and gets because of it a positive buzz for her line. Jenny begins to think that she doesn't need Eleanor anymore and can make herself a name in the fashion industry. She meets the model Agnes, who acknowledges her talent and wants to help her. While Jenny is about to become a star in the fashion world, her family is less excited. Her father Rufus doesn't like that she left school and Dan isn't the biggest fan of her latest steps either. When she finds in Nate someone who is believing in her, the two grow closer together. Nate helps Jenny out wherever he can and rescues her from a dangerous situation when she is about to pose half naked for a photographer. Jenny wonders about his behavior and wants to know why he cares so much about her. Nate can give an answer, when Jenny kisses him. She regrets it the second after and wants to leave, but Nate holds her back and the two fall into a passionate kiss. While Nate is realizing that he has feelings for Jenny, Dan finds out about them and is not happy at all. With all the problems Nate and Jenny decide to go their separate ways. Nate writes Jenny a letter in which he confesses his feelings for her, before he leaves town for awhile. But because of Vanessa's jealousy, Jenny doesn't get the letter and wants revenge on Vanessa when she finds out that she and Nate are together. With her scheme she leaves Nate disappointed and the two seem to be thrown apart.
Jenny tries to get back to things how they used to be and concentrates herself on school. When Blair's graduation's day is coming, it's all about crowning a new Queen Bee. Jenny doesn't want to join the race in the beginning, but when she sees that everyone else but her would make the life at school for many others miserable she rethinks her decision. In the end, Blair tells Jenny with a friendly advice that she is her queen and then crowns her in front of the entourage.
Rufus Humphrey - Father
Alison Humphrey - Mother
Dan Humphrey - Brother
Scott Ronsson - Half brother
Asher Hornsby (dated)