Jennifer Tallulah Humphrey is one of the characters in both the Gossip Girl and The It Girl series of novels by Cecily von Ziegesar. She is portrayed by Taylor Momsen in the Gossip Girl television adaptation on The CW.
Novel series
Gossip Girl
Jennifer Humphrey is the daughter of Rufus Humphrey, an editor of Beat poets who has never been published himself, and Jeanette Humphrey, who ran off with a European aristocrat. She has an older brother, Dan Humphrey, an aspiring writer. Jenny is a student at the Constance Billard School for Girls, a small, elite, all-girls school on the Upper East Side that Serena van der Woodsen and Blair Waldorf also attend. In the book series, Jenny is described as a short, well-endowed brunette, but the television show depicts her as tall, skinny and blonde.
In the Gossip Girl prequel It Had to Be You, Jenny is noted for having a rather flat chest until she begins taking breast enlargement supplements, which are the cause of her DD cup size.
The It Girl
Jenny is the protagonist of the book series The It Girl, which shows her new life after she gets expelled from Constance Billard and starts at Waverly Academy in upstate New York. In The It Girl, Jenny tries to reinvent herself as a "popular and sophisticated city girl" and leave behind the person she was at Constance. When Jenny arrives at Waverly, she finds the students even more attractive, athletic, and intimidating than she had imagined. Jenny then meets her two new exceptionally beautiful and popular roommates: lithe and blonde Southern girl Callie Vernon, and red-headed, green-eyed, sophisticated New Jerseyan Brett Messerschmidt. She quickly learns that she has replaced their old best friend, the extremely attractive and notorious Tinsley Carmichael. Jenny can't help but feel that sleeping in such a lucky bed must rub off.
TV series
Season 1
Jenny Humphrey is introduced in Season 1. A pretty, blonde freshman at Constance Billard, she tries desperately to fit in with Blair's clique, but Blair makes it difficult for her, subjecting Jenny to the rules of high school hierarchy. A possible friendship ends when Blair discovers Nate's lingering feelings for Serena and Jenny's interest in Nate, entailing further cruelty to Jenny. When Blair's affair with Chuck Bass is exposed, Nate approaches Jenny and Blair's affair is made public. Blair's friends shun her for her hypocrisy and establish Jenny as the new Queen Bee of Constance Billard. Despite being one of the school It Girls, she is driven to prove herself. Lacking self-confidence because she is not as rich as the other girls, she sells her sewing machine and barters an expensive dress she stole from one of her friends. When Blair throws her a surprise birthday party, the other girls discover that Jenny stole the dress, bringing Blair's scheme to fruition. Jenny retaliates by bringing Nate with her to Blair's victory party and winning the girls to her side. Jenny and Blair then struggle for the position of Queen Bee. Jenny thinks she's found true love with Asher Hornsby, but their romance is short-lived when she discovers that he is gay. He convinces her to say that she lost her virginity to him in order to dispel the rumors that he is gay, promising that as long as she pretends it's true, he'll give her privileges that the Upper East Side can offer. But Blair and Eric out Asher at his own party, and Jenny confesses that she lied about having sex with him. Blair's clique abandons her once again, and she later finds Blair to tell her that she's won as it's "not worth it". In the season finale, Jenny receives an internship at Blair's mother Eleanor's company.
Season 2
At the beginning of season 2, Jenny spends her summer working hard as a new intern for Eleanor Waldorf Designs. She apologizes to Eric for her behavior the previous season. He forgives her and invites her to the White Party in the Hamptons, where he introduces her to Tinsley Mortimer and she proves her worth to one of Eleanor's supervisors.
Eleanor fires Jenny after a critical remark about one of her dresses, but during a citywide blackout, Eleanor realizes her talent and hires Jenny. After constant harassment by Blair's minions, Jenny decides to skip school to pursue a future in fashion.