The 10 Saddest Things About Jenny, Ranked


When Gossip Girl kicked off, Jenny Humphrey was a junior at Constance Billard. Above all else, she wanted to feel like she belongs there, even though both she and her brother Dan were branded as outsiders. After all, they lived in Brooklyn and didn’t have filthy rich parents. She started off as a nice and naive girl, but the cruel environment soon shaped her into a cold and dismissive goth girl.

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Jenny left New York after the season 3 finale. Considering she was the youngest of the main characters, one would think that someone would take extra care of her, but she had no such luck. It’s really not fair that she had to endure so much suffering. 

10 She Was Desperate For Validation

Blair Waldorf Jenny Humphrey Gossip Girl

Just like other 14 year-olds, Jenny was desperate for validation. In her mind, she wasn’t worth anything unless she was a part of the high society, consisting of Blair Waldorf and her dim-witted squad. They judged her just because she wasn’t as wealthy as they were, which was outright cruel.

If only Jenny knew her worth should come from within, she would save herself a lot of trouble. Everything that happened to her in Gossip Girl can be traced back to her need for validation.

9 She Was Branded With The “L” Word

Blair and her pack of friends branded Jenny with the “L” word: liar. They made it seem like it was the biggest deal ever, even though that’s what everybody does on a daily basis in their school.

Jenny was lying to get their approval. If they really cared about her, they would’ve reassured her, not make her feel even worse about herself.

8 She Has No Real Friends

Jenny tried to fit in so badly that she was willing to do anything to gain some friend. She was willing to lie, scheme and pretend she is someone she is not. She got into Blair’s close circle eventually, but those girls weren’t her real friends. Eric was the closest thing she had to a friend, but she didn’t really respect him all that much.

Real friends would accept Jenny as she was. She had a lot to bring to the table: she was a creative designer, she always rocked amazing outfits, and she was really mature for her age.

7 She Was Arrested Because Of Blair

Blair and Jenny were the perfect frenemies. Blair has done pretty bad things to Jenny, but Jenny knew how to return the punch and challenge the self-proclaimed Queen B. Blair was organizing a sleepover and before turning in for the night, she urged Jenny to go in her mother’s shop and steal a jacket. It was a prank: Blair set her up, so the alarm went off and Jenny was caught by the police.

Jenny put her lying skills to use and talked her way out of this mess. Blair went too far here; getting the police involved is no joke.

6 She Was Bullied

Jenny was bullied by both Chuck and Blair. When Jenny had a date over at the penthouse and they played monopoly, Chuck tried to humiliate her by saying: “What a shock, the girl from Brooklyn’s a renter.” He also assured her that if she hears creams coming out of his bedroom, that it’s fine. Talking about creepy …

Blair, too, bullied Jenny – actually, there isn’t a single person she didn’t bully at some point. It’s no wonder Jenny turned into the biggest and baddest bully herself. Curiously enough, Blair was hailed a strong independent woman when she was being mean, while Jenny got so much hate for the exact same behavior.

5 Her Parents Failed Her

Rufus deeply cared about his daughter. In “The Blair B*tch Project”, they had one of the first major fall-outs. Jenny told him that she sold some of her stuff in order to better fit in at her school. Rufus (correctly) told her that she doesn’t have to do those things, but it’s like he is forgetting that he is talking to a teenage girl.

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Jenny was a very difficult child, but what she needed most was guidance and support. Rufus was frantically trying to draw boundaries, which only pushed Jenny further away from him. Meanwhile, her mother wasn’t even in the picture. Luckily, everything turned out fine. Jenny even went to live with her mother.

4 Agnes Slipped Drugs Into Her Drink

agnes drugged jenny

In “The Empire Strikes Jack”, Agnes roofied Jenny after her fashion show. Then, she was dropped of in some creepy bar where a bunch of guys were taking shots. Luckily, Nate went looking for her and saved her. Jenny deserved to celebrate her success with those who cared about her, but instead she almost got assaulted. No one deserves what Jenny went through.

Since we are talking about drugs, let’s mention another drug-related storyline: Jenny was forced to sell drugs for Damien Dalgaard.

3 Eleanor Took Credit For Her Work

The highly-esteemed Eleanor Waldorf took advantage of the young designer and never gave her any credit for it. The woman was outright stealing her designs. She should have been a mentor to Jenny, but she bullied her just like her daughter did. We felt very sorry for Jenny during her internship, but at least she stood up for herself and walked away.

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Many fans haven’t noticed this small detail about Jenny: regardless of her past with the Waldorfs, she was still rocking Waldorf bags and even agreed to do her very own line for this family who was nothing but unkind to her. It doesn’t really add up, but the show is filled with all kinds of character inconsistencies.

2 She Was Assaulted By Chuck

Chuck and Jenny kiss

In the pilot episode, Chuck tried to hook up with Jenny, even though she was just fourteen years old at a time. He lured her to somewhere private so “they could talk.”

She actually thought he really just wanted to talk and was visibly uncomfortable with him kissing her. Luckily, he stopped pretty fast, but then made her drink champagne. Fast-forward to the last we see of Little J, she just lost her virginity to Chuck. She felt alone and deserted.

1 She Was Banished By Blair

After Jenny had sex with Chuck, Blair banished her from the city. First of all: no New York-based teenager in all human history had the power to banish people, but let’s just pretend that’s something that can happen in the Gossip Girl universe.

Second of all, why was Jenny punished for sleeping with Chuck? She was the victim here and it’s really messed up how the show pushed the narrative of Chuck and Blair being couple goals, while ignoring the fact that he is a sexual predator.

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Updated: December 6, 2020 — 1:00 am

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