Jennifer Tallulah Humphrey

Jennifer Tallulah "Jenny" Humphrey was a season regular in the hit TV series Gossip Girl and the book series of the same name. The television character was portrayed by actress, singer and model Taylor Momsen. Jenny was a main character until she was banished at the end of Season 3. Since then she has been a recurring character.

Personolaty
Jenny remains determined and self-conscious the entire way through the seasons but she matures and changes as more and more things happen to her. In Season 1 Jenny is shy, quiet and trusting. She wants to be one of the girls that she admires and will do anything to become one of them, going as far as to steal and sell all of her stuff. She is artistic and very fashionable managing to make her own clothes and design clothes for other people. In Season 2 Jenny has become ignored and an outsider just like her brother Dan, but she has also become hard-working and honest. She works for Eleanor Waldorf Designs and loves having a job which she is very good at. She remains to be a good sister, she always looks out for Dan and is ecstatic when he gets back together with Serena. As the season progresses she becomes more independent, ditching Eleanor and then Agnes in an attempt to become a better fashion designer. In Season 3 Jenny has gone through a huge transformation, she starts the Season her normal self but she soon becomes bitchy, dishonest, disrespectful and horrible. She hurts the people she loves until eventually she realises she isn't herself anymore. When she leaves she vows to be herself again away from all the mean girls of the Upper East Side. When Jenny returns it is quickly shown she has no want to be her old self again, in fact she agrees to stay in her apartment and not go against Blair. This is quickly diminished when she makes team Brooklyn again with Juliet and Vanessa, they take down Serena and break up Blair and Serena's friendship. She decides she hasn't changed, apologizes to Blair and temporarily earns her forgiveness before going back to Hudson to live with her mom once more.

It Girl Novel
The main character of The It Girl, Jenny Humphrey arrives at Waverly Academy after having been expelled from the Constance Billard School for Girls. Jenny is eager to reinvent herself as 'New Jenny,' a more confident and more popular version of her former self, and to make an impression on her new classmates. Described as being short, with curly brown hair and large brown eyes, Jenny's otherwise innocent appearance is marred by her double-D breasts. Jenny is excited to discover that her two new roommates—Callie Vernon and Brett Messerschmidt—are two of the most popular girls at Waverly.

Although Jenny gets off to a rocky start at Waverly, the attention she receives from the other students generally gets more positive as the series progresses. In the first book of the series, it is noted that Jenny seems to share certain traits with Tinsley Carmichael, who, prior to Jenny's arrival, was the most popular girl at Waverly before getting expelled before the beginning of the series. Despite being a new student at Waverly, Jenny lands herself a string of boyfriends - namely, Easy Walsh, Julian McCafferty and Drew Gately. Jenny's relationships are often short-lived, with each boy she dates showing up unexpectedly in her life just as her previous relationship is winding down. In the final novel, Julian unexpectedly shows up to her car and ask that they maintain contact over the summer. Jenny agrees and gives him a hug before leaving, implying that they will become a couple again. Jenny gets off on the wrong foot with Tinsley Carmichael when she returns to Waverly and despite Jenny's attempts to get Tinsley to like her, it is clear that Tinsley is jealous and annoyed that Jenny is taking her spot as Waverly's most popular girl. The two of them are frequently involved in some form of conflict, with Tinsley's main goal of turning the other students of Waverly against Jenny.

Jenny is very artistic and in fact got into Waverly on the strength of her art portfolio. She takes advanced art classes despite being a sophomore. She joins the field hockey team and proves to be a good player despite having no previous experience. Throughout the semester she keeps in close contact with her father, often e-mailing and texting him about her classes at Waverly.

Season 1
Desperately trying to fit in with Blair's clique, Blair makes fitting in difficult for her as she subjects 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 that entails further cruelty on Jenny. However, when Blair's affair with Chuck Bass is exposed, Nate approaches Jenny and rumors of 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, but her low self-confidence that stems from not having the same privileged financial status as the other girls, provokes her to sell her sewing machine and barter 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 full circle. Jenny retaliates by bringing Nate with her to Blair's victory party and persuades the girls to her side. Jenny and Blair then struggle for the position of Queen Bee. When Jenny thinks she's found true love with Asher Hornsby, 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 put the rumors of him being gay to rest, and as long as she pretends it's true, he'll give her privileges that Upper East Side can offer. However, 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. Jenny Humphrey is introduced in season one. She is a cute, blonde freshman at Constance Billard.

Season 2
At the beginning of season two, Jenny spends her summer working hard as a new intern for Eleanor Waldorf designs. She apologizes to Eric for her behavior in the previous season. He forgives her and invites her to the White Party in the Hamptons where he introduces her to Tinsley Mortimer and where she proves her worth to one of Eleanor's supervisors. Eleanor fires Jenny after a critical remark on 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. When Blair and Serena have another fight concerning Serena's growing popularity, Jenny is dragged into their fight during Eleanor's fashion show and is subject to Blair's torture when she changes the seating arrangement that Blair had initially planned. Blair informs Rufus that Jenny has been skipping school and he confronts her. Blair attempts to sabotage Jenny’s work in the show but Jenny improvises, proposing that Serena and the socialites walk the runway. In an effort to ruin Serena, Blair switches the final dress with one that Jenny made, drawing Eleanor's ire. Despite this, the dress is a huge hit with the audience and the fashion show is a big success. Jenny realizes Blair's frustrations regarding her friendship with Serena, commenting that they have worked hard for what they’ve wanted and Serena just glides through. Eleanor later praises Jenny Humphrey for her work. Rufus eventually agrees to Jenny being home schooled after seeing how committed and good at her job she is. At work, Jenny befriends a model named Agnes Andrews, who convinces her to start her own fashion line. Realizing that working for Eleanor won't help her develop as a designer and that Eleanor herself has begun to take advantage of Jenny's talents in fashion, Jenny leaves.Jenny also begins a short relationship with Nate when they share a passionate kiss after he rescues her from being taken advantage of by an older photographer. Jenny and Rufus argue over her quitting Eleanor’s and Jenny moves out of the Humphrey’s apartment and moves in with Agnes, who suggests that they plan a guerrilla fashion show at the charity gala honoring Lily and Bart.The show is a big success but Vanessa witnesses her kissing Nate thereby straining their friendship and Rufus tries to get her arrested but was stopped by Lily. Due to Agnes' fiery temper and their growing disagreements over the clothing line, the pair have trouble closing a business deal. Jenny steals Agnes’ contact list, attempting to make a deal by herself. Upon learning of Jenny’s betrayal, Agnes burns all of her dresses and kicks her out of her apartment, leaving her with nothing. Upon learning that she is too young to start her own business, she attempts to file for emancipation but Rufus refuses. On Thanksgiving, Lily finds the papers after discovering that Jenny has been hiding in their apartment with Eric, and warns Rufus. Rufus and Jenny reconcile their relationship, after a little persuasion from Eleanor and she returns home. During the Snowflake Ball, Jenny learns that Vanessa and Nate are back together even though Vanessa was aware of Nate's feelings for her. Nate breaks up with her after she helps to humiliate Vanessa at the ball. Jenny returns to Constance and is forced to contend with Blair’s minions. During the season finale and Serena’s hunt down for Gossip Girl, Jenny decides to compete to be the next Queen Bee after Blair leaves. She almost drops out, but Blair gives her a touching speech about keeping her eye on the prize. In the end Blair chooses Jenny and crowns her Queen of Constance.

Season 3
After Jenny fails to bring about egalitarianism at Constance, she resolves to rule as Queen Bee with her own group of minions. With her new position and wealth, Jenny’s social climbing persona resurfaces and she begins to erase her former Brooklyn self, throwing away her homemade clothes and sewing machine. Worried that Jenny is turning into another regular Queen Bee, Eric and Jonathon attempt an intervention but as a result are humiliated by Jenny and her clique. Eric teams up with Blair to take down Jenny at the Cotillion Ball by sabotaging her escort. The plan backfires however and Jenny instead secures none other than Nate to escort her, winning her the respect of the other Queens at every other prep school on the Upper East Side. As a consequence of Eric’s scheming, Jonathan breaks up with him and a rift emerges in Jenny and Eric’s relationship. Chuck introduces her to Damien Dalgaard, son of the Belgian ambassador who works as a drug dealer to make his own money. Jenny liking his wild lifestyle, eventually strikes up a relationship with him and aids him in supplying drugs to his customers while sharing in some of the profit, even stealing some of Lily’s “headache pills”. Eventually Lily and Rufus find out about the drugs, which Damien covers up with a story about his father. Against Rufus’s will, Jenny continues her relationship with Damien who seems interested in taking it further. Jenny, who is a virgin, backs out at the last minute causing Damien to break up with her, leaving her to face her family. On Rufus’ suggestion, Eleanor reemploys Jenny to help out with her upcoming fashion show. Jenny is happy to be back, but is shocked to learn that one of the models she’ll be working with is her old friend Agnes, who, after the show finishes, takes revenge on Jenny by drugging her and leaving her in a bar to be taken advantage of. Jenny is rescued by Nate, however before anything happens to her. Because of this though, Jenny’s feeling towards Nate reawakens and she aspires to win him over. She tries to kiss him but he resists her advances because he sees her only as a friend and because he is dating Serena. Jenny attempts to sabotage Serena and Nate’s relationship by lying to Serena and implying to Nate that she is having an affair with Carter Baizen. Jenny’s attempts fail, and her relationship with both is left tenuous after Nate kicks her out of his apartment. At a gala event where Serena’s recently returned father William van der Woodsen is making a speech, a former client of Damien’s approaches Jenny, angrily telling her the drugs she sold her (Lily’s cancer medication, as was recently revealed) gave her a yeast infection. Rufus overhears this and grounds Jenny to the Humphrey apartment in Brooklyn. During her punishment, Jenny researches Lily’s medicine and informs Chuck via telephone that there is something very wrong about the medication that Serena’s father is prescribing her. It is discovered that, William has lied to Lily about her condition and has been giving her drugs that in fact make her sick in a plot to win her back off Rufus. Seeing an opportunity to break up Rufus and Lily and return her family to the way it was before, Jenny attempts to sabotage Blair, Chuck and Nate’s plan to unveil William’s deception. When William is about to be held accountable, she quickly runs to William and warns him, telling him that the police will be coming to get him, and urges him to escape. Back at the van der Woodsen penthouse she reveals that it was she who warned Dr. van der Woodsen and that she wishes her family can go back to normal stating "When I lived in Brooklyn, I may have had to ride the subway to school, and make my own clothes, but at least our family was happy". Rufus says that the only thing that needs to return to normal is Jenny. Eric is hurt by Jenny's attempt to leave the family, and says that if she wants out, no one is forcing her to stay. Jenny hits rock bottom after sending a picture of Dan and Serena in bed together to Gossip Girl, jeopardizing Dan and Nate’s friendship, Dan and Vanessa's relationship, and breaking up Nate and Serena’s relationship. Blair confronts Jenny telling her that “Nate loves Serena, Dan loves Vanessa -god knows why- and Chuck loves me. But you Jenny? No one loves you, except your daddy. And after what you pulled yesterday, who knows if that's even true anymore?” Emotionally distressed, Jenny goes to Nate’s apartment but instead finds Chuck devastated over his break-up with Blair and in her state of vulnerability, Jenny loses her virginity to Chuck. However, afterwards, Blair arrives willing to take Chuck back and Jenny sneaks out. She breaks down in tears to Eric, telling him that everyone hates her and that she slept with Chuck. Eric tells Dan, who confronts Chuck just as he is about to propose to Blair. Jenny, in tears, leaves with Rufus and Lily. A week later, she says her goodbyes to her family and leaves to finish out high school with her mother in Hudson.

Season 4
Jenny has been living in Hudson with her mother since May due to the troubles that occurred in "Last Tango, Then Paris", where she caused an uproar with Serena and Dan when she sent a picture of the two of them in bed together, which lead to the breakup of both Dan and Vanessa, and Serena and Nate. Later as she was upset she went to Chuck’s apartment and slept with Chuck, which lead to Blair breaking up with Chuck and banishing Jenny from New York City. The end of episode "Goodbye, Columbia" shows Chuck talking on the phone to Veronica (a woman who works with Tim Gunn) regarding an interview with Gunn for a returning Jenny. Jenny returns to New York in the episode "Easy J" and has a fight with Blair. Tired of Blair's schemes she sends a Gossip Girl blast to everyone about losing her virginity to Chuck and reveals the secret that both Chuck and Blair wanted to hide. She then returns to Hudson after telling Chuck and Blair that if their vindictive games towards each other continued, they would destroy each other. Later, Jenny lies and says she has a test to study for and that is why she can't make it to the Upper East Side for Lily and Rufus' anniversary. Eric and Dan know that she is afraid to come home because she is afraid of Blair and Chuck and of turning into the person she used to be. So Dan tries a few schemes himself but realizes that he is turning into Blair and Chuck as well. Jenny later becomes involved in a scheme with Juliet Sharp and Vanessa in order to bring down Serena and turn everyone against her. But when Serena ends up in the hospital after being drugged by Juliet, Jenny tells Juliet that she is going to come clean with everyone about their scheme, but Juliet warns her that she will be going down alone. When Jenny appears at the hospital, Vanessa has already penned the entire scheme on her and unable to defend herself, she leaves, showing up at Blair's later that night, telling her that Juliet was behind everything and that she and Vanessa were merely accomplices. To prove her story, she hands Blair Juliet's masquerade mask and has temporarily earned Blair's forgiveness. After confessing to Blair, she says that she would love to help her take down Juliet, but she should instead return to Hudson, rather than become involved in another scheme.