Gossip GirlJenny Humphrey shared many of her brother’s traits. Like Dan, he had integrity, had great potential, and knew his place in the world from a young age. But Jenny was never as good at holding a grudge as Dan, which is why at the end of the show she was able to make amends with her biggest bully, Blair Waldorf.
But Jenny has also made some mistakes and there have been times when she has been irrational. But that doesn’t take away from the fact that Upper East Side residents relentlessly harassed and socially bullied her when she was just a child.
10 Teenager: when she missed the point of outshining Blair as queen
When Jenny successfully dethroned Blair, she simply takes over his mantle and resumes her toxic dominance instead of making changes. This is usually what a teenage B queen would do when given a chance to make people listen.
“There are no more hierarchies. MET steps will no longer be restricted to a certain crowd. No more Nairtinis, no more headbands … This is a new era! Let freedom reign! “She exclaimed. Rather than ditch the title entirely, she simply unleashed her own reign of terror, proving once and for all that she was no better than Blair, but simply jealous.
9 She knew beyond her years: she realized her fashion ambitions very early
Many teenagers aspire to be a part of the fashion industry, but Jenny Humphrey, despite not having too many A-lister or Upper East Side connections, manages to get a really stellar job before she even graduates from high school. This is really amazing because designers or creatives usually don’t start working professionally until they have at least enrolled in fashion school.
The fact that Jenny was so confident in her abilities and knew exactly what she wanted to do and had started working for a major designer and even understood the rigors of design, as a teenager, is pretty amazing.
8 Teenager: when he took Blair’s banishment seriously
Realistically speaking, Blair’s banishment had no real credibility and functionally it couldn’t do Jenny any harm if she didn’t respect it. However, Jenny was only a teenager and she was quite overwhelmed by how things had turned out with Chuck, it was quite natural for her to be scared.
However, as she grew older, Jenny might have really questioned the legitimacy of this so-called banishment, especially since so much time had passed. In season 4, he arrives in Manhattan, but it becomes very apparent that he is still well aware of his ban and this may have been his teenage anxiety that he simply never resolved.
7 She knew beyond her years: when she missed an art unveiling to fix Blair’s dress
Jenny was criticized by Alison for missing her art opening and going to Cotillion, but this was quite unfair. Jenny saw Blair’s dress rip during a fight between Nate and Carter. Blair promised to forgive Jenny if she stayed and fixed her dress, and this caused Jenny to miss the art unveiling.
Alison urges Jenny to think about the type of person she was becoming, but Jenny actually chose to be a decent person and helped someone who was in a crisis. So he was definitely being the mature and reasonable person because someone younger may have thought selfishly and just abandoned Blair.
6 Teenager: when he snuck into the masked ball
Any teenager would want to sneak into a classy masquerade ball, especially if they are told they can’t attend. In an episode titled “The Handmaid’s Tale,” Jenny, along with Vanessa, can sneak into the masked ball that Blair forbade her to attend.
Jenny exchanges masks with Serena and meets Nate Archibald, who mistakes her for Serena, professes his love for her, and kisses her. Although Jenny escapes, she tells Blair what she did and Blair, of course, attacks her.
5 She knew beyond her years: when she realized she was being exploited
Not all young creatives or designers realize that they are being exploited by their bosses and sometimes they just take advantage of it to be in their good books. But Jenny had a lot of integrity and believed in her own abilities. Jenny was working as an apprentice to Eleanor Waldorf and noticed that many of her designs appeared in the Eleanor line, although she was never allowed to meet buyers.
Jenny picked up on Eleanor’s tricks pretty quickly and decided to leave. She even took her signature creation with her, which Eleanor was about to show off to buyers and pass off as her own.
4 Teen: when he kissed Nate
Almost all teenagers at some point have fallen in love with their older brother’s friend or classmate. Jenny was no different, although she didn’t do it in an obvious way. She didn’t mindlessly fantasize about Nate or scribble his name in her books, and they had actually managed to cultivate a friendship.
And it was not unlikely that Jenny was attracted to Nate, but acting on that attraction, especially while Nate was staying in her and Dan’s loft, was quite irrational and boyish.
3 He knew beyond his years: when he tried all means to find investors
Finding investors for your fashion line is not something all teenagers deal with, but then again, they don’t usually have the talents of Jenny Humphrey. Jenny was a prodigy and was aware of her potential to be the next big thing in design. She didn’t want to waste time starting her own fashion line. She, of course, needed funding and in fact managed to come up with ingenious ways to get funders.
She blocks Bart Bass’s benefit and even steals Agnes’s client list after realizing that Agnes doesn’t take her future seriously at all. Although this may sound a bit vague, Jenny’s courage and determination were definitely admirable.
two Teen: lashed out at Nate for worrying about her
When Nate sees Jenny dancing in lingerie with another model and Agnes, he’s obviously worried that Jenny was still a minor and his best friend’s sister. Obviously, Nate felt somewhat responsible towards her and also wanted to keep her safe.
Nate basically takes Jenny out of Agnes’s lair, but Jenny yells at her that she’s mad at Nate for sticking her nose into her affairs. This scene had the cliché of ‘you’re not my dad’ where Jenny just acted like a distraught teenager because an older figure won’t let her behave recklessly.
1 She knew beyond her years: when she went back to work for Blair
The fact that Jenny agreed to work with Blair despite her bitter history is truly admirable, especially since she is entitled to harbor some tense emotions about how Blair banished her from Manhattan.
But Jenny decides to be the bigger person and really make amends. She had moved to London to pursue fashion at Central Saint Martin at the end of season 5, and in season 6, she is a newly minted designer who agrees to create a line with Waldorf Designs called J for Waldorf.
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