Jenny Humphrey might just be one of the most divisive characters in Gossip Girl — and considering there are quite a few of them, that's saying a lot. She enters the show as the picture of innocence, a girl from Brooklyn without the wealth of the families she's coming into contact with. Her severe lack of connection to the world and how often she feels ostracized makes fan sympathize with her on many occasions.
But as the show progresses and she becomes more entrenched in a world she claims she doesn't want to become, she does some pretty terrible things too. Sometimes, it's to fit in; others, it's to get ahead. But there are definitely some moments when fans really despise her and can't understand why she's done these horrible things.
Felt Bad: Entering The Upper East Side
It's impossible not to feel bad for Jenny when she first steps onto the scene. She's very out of place, doesn't have the money to afford the fashion that would make her liked at school, and she's very much bullied by Blair Waldorf as she attempts to fit in and befriend some people. She's completely judged on her lack of extravagant wealth, which isn't at all fair.
Hated Her: Becoming More Like Blair
As she begins to settle into the Upper East Side though, she ends up becoming more like Blair.
Initially, it's small things, like trying to fit in by being sneaky. Pretty soon, it becomes horrible. She makes Eric sit on the step below her because it's bad for her image to have him seen as an equal, and even dumps yogurt on Blair's head to make a point. These the kind of things expected from the mean girls of the school, which Jenny is slowly becoming.
Felt Bad: Being Taken Advantage Of By Eleanor
When Jenny gets an internship with Eleanor Waldorf Designs, it's her dream — besides the apprehension of working with Blair's family. But very quickly it becomes obvious that the job isn't easy, and she spends a horrific amount of time being taken advantage of. She plays along with it, because she wants a letter of recommendation and to become known in the fashion industry, but it eventually goes as far as Eleanor actually stealing her designs. Jenny eventually walks out, but not before being strung along on false promises for letting someone else take credit for her talent and work.
Hated Her: Ruining Her Relationship With Rufus
It's hard to watch her become so involved with the fashion world that she makes bad choices that ultimately ruin her relationship with her father.
Rufus isn't exactly the perfect parent, but it's clear that he loves Jenny and is trying. Jenny, however, is just determined to leave school and it goes as far as her asking for emancipation. It's hard to imagine the hurt of your daughter taking legal action so that you aren't her father anymore and as much as Rufus wasn't handling anything well, this hurt to watch.
Felt Bad: Watching Her Spiral
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.
Hated Her: Sleeping With Chuck
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.
Felt Bad: When She Was Forced To Leave New York
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.
Hated Her: Pursuing Nate
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.
Felt Bad: Her Disastrous Party
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.
Hated Her: Conspiring Against Serena
She conspires with Juliet and Vanessa against Serena, and it all goes too far when Serena ends up actually drugged. Jenny may never have expected it to get this far, but what did she expect from conspiring with a woman she barely knows, in a world that can be all too dangerous? She feels bad afterward, but Serena is put in a lot of danger.