Gossip Girl's Jenny Humphrey shared many of her brother’s traits. Just like Dan, she had integrity, she had a lot of potential and she knew her place in the world from a very young age. But Jenny was never really as good as Dan at holding grudges, which is probably why at the end of the show she was able to make peace with her biggest bully, Blair Waldorf.
But Jenny has made some mistakes as well and there have been times when she has behaved irrationally. But that doesn’t take away from the fact that she was relentlessly bullied and socially intimidated by Upper East Siders when she was just a kid.
Teenager: When She Missed The Point Of Upstaging Blair As Queen
When Jenny had successfully managed to dethrone Blair, she simply takes over her mantle and resumes her toxic dominion instead of actually making changes. This is usually what a teenage Queen B would do when given a chance to actually make people listen.
“There is no more hierarchy. The steps of the MET 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. Instead of doing away with the title altogether she simply unleashed her own reign of terror, proving once and for all that she wasn’t better than Blair but simply jealous.
Wise Beyond Her Years: Realized Her Fashion Ambitions Very Early
Many teenagers aspire to be a part of the fashion industry, but Jenny Humphrey, in spite of not having too many A-lister or Upper East Side contacts, manages to accomplish some really stellar work even before she graduated high school. This is really quite staggering because usually designers or creatives don’t start working professionally until they have at least enrolled at fashion school.
The fact that Jenny was so confident about her skills and knew exactly what she wanted to do and had started working for a major designer and even understood the rigors of designing, as a teenager, is quite astonishing.
Teenager: When She Took Blair’s Banishment Seriously
Realistically speaking, Blair’s banishment didn’t have any real credibility and couldn't functionally do any harm to Jenny if she didn’t respect it. However Jenny was just a teen and quite overwhelmed at how things had turned out with Chuck, it was quite natural for her to just be scared.
As she grew up though, Jenny really could have questioned the legitimacy of this so-called banishment especially since so much time had passed. In season 4 she does come into Manhattan but it becomes very evident that she’s still very aware of her ban and this may have been her teenage anxieties which she simply never resolved.
Wise Beyond Her Years: When She Missed An Art Opening To Fix Blair’s Dress
Jenny was criticized by Alison for missing her art opening and going to Cotillion instead, but this was rather unfair. Jenny saw Blair’s dress ripping during a scuffle between Nate and Carter. Blair promised to forgive Jenny if she stayed and fixed her dress, and this caused Jenny to miss the art opening.
Alison urges Jenny to think about the kind of person she was becoming, but Jenny actually chose to be a decent person and helped out someone who was in a crisis. So she was definitely being the mature, reasonable person because someone younger may have thought selfishly and simply abandoned Blair.
Teenager: When She Snuck Into The Masked Ball
Any teenager would want to sneak into a super classy masked ball especially if they are told they can’t attend. In an episode titled "The Handmaiden's Tale", Jenny, along with Vanessa, is able to sneak into the Masked Ball that Blair forbade her to attend.
Jenny trades masks with Serena and runs into Nate Archibald, who mistakes her to be Serena, professes his love for her, and kisses her. Though Jenny gets away, she tells Blair what she did, and Blair of course lashes out at her.
Wise Beyond Her Years: When She Realized That She Was Being Exploited
Not every young creative or designer realizes that they are being exploited by their bosses and at times they just roll with it to be in their good books. But Jenny had a lot of integrity and she believed in her own skills. Jenny was working as an apprentice to Eleanor Waldorf and she realized that many of her designs were actually featured in Eleanor’s line although she was never allowed to meet the buyers.
Jenny caught on to Eleanor’s tricks pretty fast and decided to leave. She even took her signature creation with her which Eleanor was about to show the buyers and pass off as her own.
Teenager: When She Kissed Nate
Almost every teen has at some point had a crush on their older sibling’s friend or classmate. Jenny was no different, although she didn’t go about it in an obvious way. She didn’t mindlessly fantasize about Nate or doodle his name on her books, and they had actually managed to cultivate a friendship.
And it was not unlikely for Jenny to be attracted to Nate, but acting on that attraction, especially while Nate was staying at her and Dan’s loft, was quite irrational and juvenile.
Wise Beyond Her Years: When She Tried Every Means To Find Investors
Scouting investors for their fashion line is not something every teenager busies themselves with, but then again they don’t usually have Jenny Humphrey’s talent. Jenny was a prodigy and was aware of her potential to be the next big thing in design. She wanted to waste no time starting her own fashion line. She, of course, needed funding and actually managed to devise crafty ways of getting financiers.
She crashes Bart Bass’ benefit and even steals Agnes’ list of clients after she realizes Agnes isn't serious about their future at all. Though this may sound a bit sketchy, Jenny’s grit and determination were definitely admirable.
Teenager: Lashed Out At Nate For Worrying About Her
When Nate sees Jenny dancing in her lingerie with another model and Agnes, he is obviously concerned because Jenny was still a minor and his best friend’s sister. Nate obviously felt somewhat responsible towards her and also wanted to keep her safe.
Nate basically drags Jenny out of Agnes’ lair but is yelled at by Jenny who's angry at Nate for poking his nose in her affairs. This scene had the cliché ‘you’re not my dad’ vibe where Jenny simply behaved like an angsty teen because an older figure won’t let her behave recklessly.
Wise Beyond Her Years: When She Came Back To Work For Blair
The fact that Jenny actually agreed to work with Blair despite their bitter history is really admirable, especially because she is entitled to harbor some fraught emotions over how she was banished from Manhattan by Blair.
But Jenny decides to be the bigger person, and actually make peace. She had moved to London to pursue fashion at Central Saint Martin at the end of season 5, and in season 6, she’s a newly minted designer who agrees to create a line with Waldorf Designs called J for Waldorf.