Jenny Humphrey starts out as the baby minion to Blair but eventually becomes “queen” in her own right at Constance St. Jude, the school all the girls attend in Gossip Girl. She takes on Blair for the role of expert schemer and defies her parents in ways most 15-year-olds would never dream of doing.
Eventually, Jenny goes back to Hudson to live with her mother, having been beaten down by the Upper East Side one too many times. Until that time (and even a few times after she left), Jenny plans and manipulates with the best. Along the way, there are many things she did that definitely wouldn’t fly today.
10 Was Bullied By Blair, And Took It
The beginning of season 1 shows Jenny as Blair’s youngest minion. Blair has her doing all kinds of grunt work to gain her favor and it is implied that if Jenny doesn’t comply, her connections in the Upper East Side will go flat.
Jenny is constantly pressured and obligated to do things that are uncomfortable for her and some that are illegal. When her father Rufus finds out that Blair is bullying his daughter, he doesn’t do much to stop it and neither does anyone else.
9 The 14-Year-Old Party Girl
In her attempt to fit in with the Upper East Siders, Jenny gets herself invited to (or crashes) several parties where there is drinking, drugs, and a lot of people that are much older than her. She stays the course and follows along with everyone else, even when it means doing drugs or drinking herself.
The adults in Jenny’s life find out about the partying and she is grounded, but no one does a thing to stop the parties or at chaperone them, at the very least.
8 Let Eleanor Take Advantage Of Her
As an intern, Jenny is supposed to be responsible for doing a ton of work with only "experience" as compensation. But she wore her own original designs to work and let Eleanor rip them off. She also let Eleanor take credit for the finale dress in the fashion show, which got a ton of praise.
In today’s world, letting this happen, without a word, would never fly, especially with all the other people that knew the designs belonged to Jenny.
7 Her Drug Dealer Phase
In season 3, Jenny and Damien Dalgaard are in a relationship and his “profession” is selling illegal prescriptions to the elite teens of the Upper East Side. Jenny gets in on the action in order to fund her reign as Queen of Constance and buy her minions extravagant gifts that keep them loyal.
In today’s world, a teenager suddenly having that disposable income would raise every red flag, and in today’s opiate crisis culture, dealing drugs would be shut down fast.
6 Pursued Nate
While Nate is still with Serena, Jenny gets it into her head that he has to be hers. She pursues him relentlessly and it was a story that the fans hated. She wanted the best of the best for her boyfriend and she didn’t care that Nate was her brother’s best friend or that he was old enough for their coupling to constitute assault.
Jenny’s single-minded pursuit would never fly today and someone, especially Nate, would have stopped her along the way.
5 Jenny The Runaway
When Rufus refuses to let Jenny live her life the way she wants, Jenny runs away with just her designs and her sewing machine to keep her warm. She partners with her wild friend Agnes, who proves to be unstable when they try to start a business promoting Jenny’s clothing designs.
Jenny considers emancipation but, before that, there are several adults who know where she is, including Agnes’s mother, who doesn’t send her home.
4 Banished From New York City
Jenny’s schemes and plans blow up in her face in the end and she is banished from New York City by Blair. Jenny takes the directive and goes to her mother’s house in Hudson, but the directive itself is something that would never fly today.
Jenny moves away from most of her family and the only life she knows because a young woman barely out of high school tells her to leave. She doesn’t go to her father or the police. She just leaves.
3 Lost Her Virginity To Chuck Bass
Jenny’s first interaction with Chuck at Blair’s Kiss On The Lips party followed with Chuck attempting to assault her, but he’s never officially accused or charged. After all her schemes, Jenny turns to Chuck to get back at Blair later on in the series, just before she’s banished from NYC.
She lets Chuck take her virginity, but she’s still only 16 and Chuck is an adult. Blair knows about this incident and others find out but Chuck is never charged with this either. These incidents would never fly today without some kind of consequence .
2 The Tim Gunn Interview
After Jenny is banished from NYC, she lands an interview for Parsons School of Design with famous designer Tim Gunn. The interview is sabotaged when Blair gets her minions to steal Jenny’s dresses and ruin them. Jenny knows that it was Blair, who practically confessed to the crime.
Jenny doesn’t charge Blair with the destruction of her property, and as original designs, they’re irreplaceable. There are ways to get proof of what Blair did, but Jenny simply lets it go.
1 Helped Juliet Sharp Get Revenge
Juliet Sharp is Ben’s sister, who was sent to jail on a lie told by Serena’s mother. Juliet lets everything get personal, and as a result, is shunned when everyone finds out what she’s done. Ben is released from prison and gets to start a new life with his name cleared. Juliet doesn’t want to let Serena get away with this and Jenny helps her concoct a plan that alienates Serena from her friends and family and leaves her out in the cold.
Juliette takes it a step further and forces drugs into Serena to the point where she’s almost dead when she is found. That wasn’t Jenny’s intention and Juliette is punished for what she did, but Jenny faces no legal consequences for her complicit actions. She set Juliette in motion and gave her the information she needed to make her plan happen. Today, not facing consequences for this would not fly.
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July 09, 2020 at 09:30PM
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