Throughout Jenny's time in New York, she had a hard time making friends. While some of Jenny's antics were questionable, her "friends" refused to show her sympathy and would turn their backs on her at the drop of a designer bag. Even Agnes, Jenny's supposed best friend and roommate, betrayed Jenny by burning her original dresses in a trash can.
Agnes not only ruined Jenny's months' worth of work but also ruined their friendship. Even though Jenny did her fair share of backstabbing, it was a direct result of a lack of healthy friendships in her life.
Maybe if Jenny had made good friends, she would've learned how to be a better one herself. Whether it was for sex or fabric patterns, Jenny was often used by other characters as a pawn. In fact, Eleanor Waldorf, Blair's mother and famous fashion designer, used Jenny constantly: eventually attempting to take Jenny's design as her own without crediting the Constance sophomore. Eleanor also made Jenny work extremely hard with little to no reward in the professional world.
This led to Jenny's outburst and termination from Eleanor Waldorf designs. However, after the way she was treated, who could blame her? Jenny was also used by Chuck as a means of feeling less alone. After seemingly losing Blair, Chuck turned to a depressed—and teenage—Jenny for company.
After taking her virginity, Chuck kept his one-night affair with Jenny a secret and got back together with Blair minutes afterward. However, once Blair found out, she forced Jenny to leave New York for good: Chuck didn't even step up to defend her. This was one of the lowest and most sympathetic moments for Jenny, she was left with nothing and no one. Even though Jenny had a supportive brother and father, it was hard for her to feel understood in her home.
After Jenny began acting out, Rufus showed little sympathy and seemed to forget that he was dealing with a teenage girl. He neglected to talk to Jenny about why she was acting out and instead chose to villainize her. In the later seasons, Jenny begins dealing drugs in order to impress her crush, Damien.
Jenny herself wasn't using, she was simply trying to gain Damien's affection. However, once her family finds out, Jenny is instantly painted as the villain without anyone caring to hear her side of the story. At the same time, Blair works with Rufus to plan an embarrassing party for Jenny; where it's revealed that she stole Hazel's mother's dress. While the girls are angry at first, they decide to forgive Jenny rather than give power back to Blair.
However, she quickly realizes she made a big mistake after Asher reveals that he is gay and only using her as a beard. At a joint party Asher and Jenny throw together, Blair and Eric reveal Asher's sexuality to everyone. After finding out, Jenny's friends become angry at her for lying about sleeping with Asher and kick her out of the group All About My Brother.
After Jenny spends an entire summer interning at Waldorf Designs, she is briefly fired by Eleanor in The Dark Night but gets her job back the same day.
After school begins and Jenny becomes worried about Blair's clique targeting her she begins to skip school to work at the atelier. However, Blair quickly figures out what Jenny is doing and alerts Rufus; who attempts to put a stop to it. When he confronts Jenny about it she tells him that she isn't planning on returning to Constance The Serena Also Rises.
Soon after, Nate moves into the Humphrey loft after Dan and Jenny discover that he is living off the bare minimum in his house. At the same time, Jenny is taking on more responsibilities at Waldorf Designs and befriends a model, Agnes Andrews , who convinces her to quit letting Eleanor rip off her designs and start her own clothing line. Later that day she hangs out with Agnes and ends up dancing with her shirt off while Agnes' boyfriend, Max, takes photos. Nate escorts her home but kisses her on the way out.
They successfully do so, and Dan kicks Nate out of the loft after he witnesses him kiss Jenny. However, Rufus is angry with Jenny for sabotaging an event and almost has her arrested. Afterwards Jenny moves out to stay with Agnes. In Bonfire of the Vanity Jenny becomes increasingly annoyed with Agnes' cavalier behavior towards the future of their line.
After she blows an important meeting, Jenny steals her list of contacts and begins to meet with them secretly. When Agnes finds out she burns all of Jenny's dresses and kicks her out of her apartment. Jenny then goes home to ask Rufus to sign papers giving permission for her to start her own line. He refuses and Jenny goes to stay at the art gallery.
The next day, she meets with a potential investor who suggests she emancipate herself to get the ball rolling on next steps. Lily finds Jenny's emancipation papers and immediately calls Rufus to tell him. She arranges a meeting between the two and Rufus tells Jenny that if she really truly wants him to sign the papers, he will. She mulls it over before ripping the papers up and tells Rufus that she doesn't want to not be his daughter.
At Thanksgiving dinner, Vanessa finds a letter Nate wrote to Jenny where he admits he has feelings for her and she steals it before Jenny can see it.
Jenny makes her a dress with zero lining, rendering the dress see through, and they arrange for Vanessa to have a spotlight shown on her. When Nate finds out what Jenny did he tells her he has no interest in her anymore It's a Wonderful Lie. In Gone with the Will it's revealed that Jenny, Dan, Serena, and Eric share a half sibling due to Rufus and Lily having had a son before any of them were born.
In Dan de Fleurette Jenny officially begins her reign as new queen of Constance. However, Blair is unsatisfied with the way she is running things and steps in. After this, Jenny begins to take her new role more seriously and becomes much like the way Blair was.
Soon after, Jenny is tested when she chooses being queen over her friendship with Eric and the two begin to fight How to Succeed in Bassness. He brings Jenny onto his operation and the two become close, eventually beginning to date in The Lady Vanished. However, since Damien is older than Jenny, he becomes interested in wanting to have sex with her. Jenny is onboard until she realizes her virginity is a bigger deal than Damien made it out to be, so the two break up The Sixteen Year Old Virgin.
Meanwhile, Jenny begins crushing on Nate and works to break up his relationship with Serena. In Inglourious Bassterds she learns Serena has left the state to find her father, William van der Woodsen , with Carter and chooses not to tell Nate the information. She uses his anger toward Serena to advance her intentions toward him but he rejects her Dr. Later that night, while researching Lily's cancer, Jenny realizes that the medicine William is prescribing her is not effective at healing.
Her whole spiral from innocent young girl to true Upper East Sider is hard to watch but sometimes, it invokes some real sympathy. For example, she goes as far as to steal a dress and as much as it's an awful thing to do, she's ultimately humiliated when Blair discovers this and outs her to all her friends.
Her model friend also burns her dresses out of spite when their business together doesn't work out, because Jenny put too much trust in the wrong person.
Chuck deserves far more hate than Jenny for this one, but fans still resented Jenny when she crawled into Chuck's bed and slept with him. It was the beginning of a huge downward spiral for the couple loved by fans everywhere, and although Jenny was clearly upset, in a bad place, and taken advantage of, fans weren't very sympathetic towards her bad decision. Blair certainly doesn't take it well though.
She has Jenny banished from New York, going as far as to tell her that if she steps foot on the island of Manhattan again, she will regret it.
As fans know by now, Blair always follows through on her ominous promises, so this was no idle threat and left Jenny forced to stay away for quite a while. She pursues Nate when he's with Serena and it's uncomfortable to watch. Nate genuinely doesn't seem to reciprocate her feelings but it doesn't dissuade Jenny, who even kisses him when he's clearly not consenting.
It throws up huge problems for him and Serena too. Granted, Jenny has just been through a horrible ordeal and is acting out, but this is not okay. Serena thinks she's doing a nice thing by throwing Jenny an awesome sixteenth birthday party, but it's clearly a misfire in judgment when Jenny doesn't love the idea.
To be fair to Jenny, she's pretty upfront about what she wants and Serena goes against her anyway, so it's no surprise to fans when she's blatantly uncomfortable despite it seemingly being a surprise to Serena.
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