Jenny Humphrey

 '''Jennifer Tallulah Humphrey is a character derived from the Gossip Girl series and is played by Brittany. She is portrayed by Taylor Momson. She is a seventeen year old human being that prefers to go by the name Jenny Humphrey. Gossip Girl has nicknamed her Little J. Jenny is a straight female and is currently single.'''

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Jenny is the fashion-obsessed daughter of Rufus Humphrey, an ex-rock star and Alison Humphrey, an artist who ran off with a European aristocrat. She has an older brother named Dan Humphrey who is an aspiring writer. With their mother Alison out of the picture, Jenny and dan resided in Brooklyn with their father for much of their high school lives, though attend a very prestigious high school on the Upper East Side as their father wishes to give them everything that he had been denied at their age.

Jenny Humphrey is a pretty, blonde freshman in high school who was always desperately trying to fit in with Blair Waldorf's clique of popular, rich and beautiful socilaites though 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 that her boyfriend Nathaniel "Nate" Archibald has lingering feelings for Blair's best friend Serena Van der Woodsen and Jenny's interest in Nate quickly entails further cruelty on Jenny. However, when Blair's affair with Nate's best friend Chuck Bass is exposed by Jenny, 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 their Manhattan high school.

Being one of the school's most popular 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 and was only trying to hide his homosexuality by dating her, stating that there is no other reason why someone would date a girl from Brooklyn. 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 Van der Woodsen (Serena's brother) announce Asher's homosexuality 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". At the end of her first year of high school, Jenny receives an internship at Blair's mother Eleanor Waldorf's fashion designing company.

Jenny spends her summer working hard as a new intern for Eleanor Waldorf designs. She apologizes to Eric for her behavior (competing with Blair). He forgives her and invites her to the White Party in the Hamptons where he introduces her to Tinsley Mortimer, one of America's most famous socialites, and where she proves her worth to one of Eleanor's supervisors.

Feeling more bold after proving herself to one of Eleanor's supervisors, Jenny makes a bold move and makes a critical remark to Eleanor about one of her dresses during a citywide blackout. Eleanor fires Jenny, though soon after, realizes her talent and hires Jenny once again, though 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 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 while working rogue as a fashion desinger. 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 Van der Woodsen (Serena's mother) and Bart Bass (Chuck's father) who went from dating, to becoming engaged and eventually married.

The show is a big success but Vanessa Abrams (Dan's longtime best friend) witnesses her kissing Nate, thereby straining their friendship and Rufus tries to get her arrested to teach her a lesson 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.

Soon after, Bart passes away, elaving Lily widowed and single, giving she and Rufus the oportunity to salvage their romantic relationship that ended decades ago. During this time, Lily legally adopts Chuck as her son upon his father's passing to allow him, rather than his biological uncle, to inherit his father's multi-billion dollar empire, Bass Industries, officially uniting the Van der Woodsen's, the Humphrey's and the Bass' once Lily and Rufus marry a short year after Bart's death.

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, and after a little persuasion from Eleanor and she returns home.

During the Snowflake Ball, Jenny learns that Vanessa and Nate were dating, even though Vanessa was aware of Nate's feelings for Jenny. Nate breaks up with Jenny upon attempting a relationship with her after she helps to humiliate Vanessa at the ball. Jenny returns to high school and is forced to contend with Blair’s minions once again. 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 their high school while she leaves for university.

After Jenny fails to bring about egalitarianism at her high school, 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 his boyfriend Jonathan 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 friendship.

Chuck introduces Jenny 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, Nate and Chuck's rival. 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 from 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.

Jenny returns to New York 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.

It isn't until Jenny learns that her family is leaving Manhattan to search for Lily and Rufus' biological child from their early twenties that they had given up for adoption that Jenny returns home long enough to pack her things and welcome a journey to Livorno, Italy to find the missing member of their family.