‣ JENNIFER ‘JENNY’ HUMPHREY | SHE/HER | 19 | BROOKLYNITE | TAYLOR MOMSEN
+ resolute, creative, challenging
- self-centered, envious, dramatic
“ who you are it’s not what you did, you’re still an innocent. ”
If she had had her choice, Jenny would not have been born and raised in Brooklyn, and she definitely wouldn’t have chosen the last name Humphrey. Last names were supposed to open doors and grant opportunities, but hers held no power, no bravado, no value. In fact, the only thing that the Humphrey name had ever awarded her was a backstage pass whenever her dad’s one hit wonder of a band, Lincoln Hawk, would play a reunion concert. But that wasn’t the life that she wanted. As a child, she would dream of far off lands with princesses, crowns, and castles. And at fourteen, she learned that those lands weren’t so far off. In fact, the ultimate dreamland was just a train ride away where the princesses were socialites, the crowns were headbands, and the castles were penthouses with a view of Central Park. Sure, she had been to Manhattan before then, even the Upper East Side to visit parks and museum mile, but the idea of American Royalty didn’t actually hit her until she was thrust into the world of Manhattan’s elite, and told to sink or swim.
When she first started at Constance-Billard School for Girls, Jenny was the picture of naïveté. From her department store accessories to her hand made versions of designer dresses, Jenny had no idea what she was getting herself into. She was deemed a project the second she walked through the doors, Blair and her merry minions immediately seeing the potential in her - a rarity for a Brooklynite. So when she was asked to use her calligraphy skills to address the invitations for the infamous Kiss on the Lips party, she couldn’t say no. That one event brought her from obscurity and gave her the tiniest taste of life on the Upper East Side, a taste that she wouldn’t soon forget. It was the life that she had yearned for, a life that she would go to any lengths, including lying to her father and stealing from her friends, to get.
From there, her life on the Upper East Side became a whirlwind. Jenny, or Little J as she was so affectionately referred to as on Gossip Girl, went from trying to please Blair, to trying to be her, and then to trying to dethrone her. And though some of her schemes for rising to the top were more successful than others, the crown for Constance Queen was not solidified on Jenny’s blonde head until after Blair’s graduation, when she handed the crown over willingly. But up until that moment, things were not easy for Jenny. She made and lost friends, she learned that money and notoriety were valued above all else, and she learned that sometimes you have to give everything up in order to pursue your dreams. Which is exactly what she did her sophomore year at Constance. She had already lost all of her so-called friends, and the only thing she could turn to was fashion and her internship with none other than Eleanor Waldorf, Blair’s mother. Jenny put everything she had into her internship and wanted so badly to impress Eleanor, that she even allowed the fashion designer to take credit for one of her own designs.
She ended up quitting school and convincing Rufus to homeschool her in order to work for Eleanor, but she soon realized that the world of fashion wasn’t all it was cracked up to be. With the pushing of her new model friend Agnes, Jenny quit Eleanor’s, left home, and attempted to partner with Agnes on creating their own line. They gained attention with a guerilla fashion show, but quickly lost it when buyers realized how immature Agnes was. And when Jenny tried to go out on her own, Agnes ensured that all of her hopes and dreams went up in literal flames, forcing Jenny to play the part of the prodigal daughter and return home and Constance.
When back in school, Jenny attempted to take down the mean girls who had made her life a living hell the previous year, but learned that Constance thrived on a hierarchy, and they didn’t know how to function without one. So after refusing to lead the mean girls, she faded into the background. But when news of her father and Lily van der Woodsen-Bass dating broke, she was forced back to the forefront of the conversation. And upon their engagement and her new approval from Blair, Jenny’s fate as the queen of Constance was finally sealed and she adorned the crystal embellished headband that declared her title to all of Manhattan’s elite.
Life as a queen wasn’t all is was cracked up to be.. When Jenny fails to unite the school and disband the monarchy, she realizes that it’s be the cruel queen everyone expects, or give up the crown for someone who will be. She, of course, chooses the former and manages to alienate herself from her original friends, mostly NR 28, who had been the only person who had truly accepted Jenny when she was still known as just a Brooklynite. She ruled with an iron fist and made sure to attack others if they dared challenge her rule. She made her societal debut with none other than Nate Archibald, and it made her practically untouchable to everyone else. And her rule is only strengthened by Lily and Rufus’s wedding, finally giving her access to the funds necessary to keep her minions in line and an Upper East Side address to keep her from being questioned as a foreign queen.
But her dreams coming true didn’t magically make her life easy or fun. People tried to challenge her and push her buttons, but her true unravelling began at Damien Dalgaard and ended in Chuck Bass’s bed. Damien turned the once sweet and innocent Jenny into a drug dealer who wasn’t afraid to alienate her family and friends until she had nothing left, including Damien himself, who left as soon as she wouldn’t give him her virginity. And in her anger, desperation, and failed scheming, she ended up sleeping with Chuck, a move she immediately regretted. She wanted to be alone, and he was the only person who didn’t hate her. And, of course, once Blair found out, Jenny was exiled from the city altogether, forcing her to pack her bags and move to Hudson with her estranged mother.
Though she was upset at first, Jenny quickly began to see the move as a positive one. She could reinvent herself, be the Jenny that she always wanted to be. And with her new spot at Waverly Academy, she could do just that. She didn’t want to be Blair, anymore. Being Blair had nearly crushed her. No, she wanted to be the blonde bombshell who could seemingly do no wrong. She wanted to be Serena. And it was simple. The students at Waverly didn’t know her, so with a few carefully crafted lies, she turned the Humphrey name into a notable one, earning notoriety with the only caveat being to keep up with her own lies for a year in which time she would graduate and go back to Manhattan a changed person. She would enroll in Parsons, avoid the bitches of the UES, become a world renowned fashion designer, and then live happily ever after.
But, of course, Manhattan never promised anyone a happy ending. And though she did return to the city a couple of times - once for her infamous interview with Tim Gunn, and the other to help take down Serena van der Woodsen once and for all - both times she ended up back on a train headed upstate with the realization that she too easily fell into the schemes of the Upper East Side, and that she could never win. From then, she vowed to get herself together and not be tempted with lures that came with being UES royalty. But now that she’s graduated Waverly with an acceptance letter to Parson’s and a summer internship with Dennis Basso in the Hamptons, Jenny’s not sure how long she’ll be able to keep her vow.
‣ SIGNIFICANT CONNECTIONS
—NUMBER 28 [former friend]: before things spiraled out of control for jenny, she and NR 28 used to be very close friends. NR 28 didn’t care about the fact jenny was a scholarship holder from brooklyn, and jenny appreciated that, especially because she knew how almost every single girl at constance was a wolf in sheep’s clothing. but once jenny got blair’s attention and started hanging out with her more and more, she and NR 28 began to drift apart until. long phone calls to chat about cute guys turned into sparse texts, and soon enough, they didn’t talk to each other anymore. jenny misses NR 28 and the friendship they once had, but she’s pretty sure that the other girl is mad at her for disappearing, so she still hadn’t made a move to try and fix their friendship.
— NUMBER 01 [friends]: NR 01 was the first person – aside from her brother – that jenny saw when she arrived in the hamptons. she spotted the girl standing in a corner, looking as lost as she was about a year ago. jenny didn’t think twice before making her way to NR 01 and introducing herself, only to be greeted with a warm smile from the other girl. the two hit it off right away, bonding over multiple things and discreetly making fun of people’s outfits.
— ERIC VAN DER WOODSEN [close friends / step siblings]: jenny and eric met through their siblings, and despite the fact that they didn’t have much else in common, they became fast friends. eric took on a protective role of her, but the more jenny got caught up in the world of the elite, the less contact she had with eric. despite all that, the two kept in touch while jenny was away, often sending texts and emails to keep each other up to date on their lives. eric is one of the people she missed most while she was away, and especially now that their parents have gotten married, she sees him as part of her family, and as someone she can rely on.