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Although Gossip Girl is full of rivalries — some very highschool, others more serious — one that remains constant throughout the seasons is that between Blair Waldorf and Jenny Humphrey.
RELATED: Gossip Girl: 5 Times We Felt Bad For Blair (& 5 We Hated Her)
At first, Jenny doesn’t seem like much of a threat to Blair. She’s a young girl from Brooklyn who’s pretty shy and just wants to fit in at school. But as time progresses, she becomes more forward and is willing to do more to fit in, and that threatens Blair. The two of them become rivals and over the course of six seasons, they each do some pretty terrible things to the other.
10 Blair: Almost Got Jenny Arrested
In the very first season, Blair almost gets Jenny arrested by staging a break-in. She’s actually pretty impressed when Jenny shows up at her penthouse unscathed, considering she was likely to get in a lot of trouble with the police. Luckily, Jenny has the idea to lie and say she’s Blair, and that lets her escape the situation.
Still, she could have gotten Jenny in a lot of trouble.
9 Jenny: Took Over As Queen
Taking over as queen of the school isn’t malicious within itself, but it dethrones Blair who sees this as the ultimate insult. Blair’s entire self-worth revolves around her reputation at the school and when she isn’t queen and Jenny Humphrey from Brooklyn is, she’s humiliated. It may seem petty to those fans who’ve long since left highschool, but it deeply affected Blair and was the worst thing that could be done to her at the time.
8 Blair: Got Jenny Caught Stealing A Dress
Jenny does something awful by stealing a dress from her friend’s mother when she needs an expensive one to wear and can’t afford it. Blair throws her a malicious party, and it’s a happy accident when the dress is discovered.
Jenny manages to get out of this later, but it’s a truly humiliating moment and it does a lot of damage to her relationship with Rufus too.
7 Jenny: Tried To Use Blair’s Mother Against Her
There are times when Jenny tries to use Blair’s mother against her while working for her, whether it’s reminding Eleanor of something Blair has done wrong or directly rubbing her in Blair’s face.
RELATED: Gossip Girl: 10 People Chuck Could Have Been With (Other Than Blair)
It’s a pretty damaging thing to do considering Blair has a complicated relationship with her mother, involving a lot of pressure and some terrible fights. Eleanor Waldorf isn’t exactly the ideal mother in many senses of the term.
6 Blair: Told Jenny’s Dad She Was Skipping School
Blair shows up at Jenny’s house to announce to Rufus Humphrey that Jenny has been skipping school to work with Eleanor. While it’s absolutely true, it’s pretty much the breaking point for Jenny and Rufus’ relationship and Blair is utterly ruthless in the damage she causes. She doesn’t care how devastating it is to Jenny.
5 Jenny: Threw Yoghurt On Blair
One of the most humiliating moments Jenny causes for Blair is when she throws yogurt on her at school. Blair has already been dethroned, so there’s very little need for this, and even Nate seems pretty disgusted by Jenny’s behavior — someone who has been watching Blair operate for a long time. It’s done out of pure spite considering there’s no message that needs to be sent at this point. Jenny just wants to cement her place as queen and, frankly, make Blair feel bad.
4 Blair: Tried To Sabotage Her Job
Blair often tries to sabotage Jenny’s job with her mother, going as far as to send models home from a catwalk show. She’s not only ruthless enough to try and ruin Jenny’s job, but willing to take her mother’s entire show down with her.
That’s what Blair’s like, and who Jenny becomes by rivaling her. They’re people who don’t care about collateral and who’s getting caught in the crossfire, which is what makes their rivalry dangerous.
3 Jenny: Sent A Gossip Girl Blast About Blair
Jenny sends Gossip Girl blasts about Blair which are damaging, but the worst thing comes from knowing exactly who Gossip Girl is in the final season. It turns out Jenny was actually conspiring with Dan all those times she sent in blasts herself, and probably had a huge hand in it every time Blair was humiliated by the website.
2 Blair: Made Her Leave Manhattan
Blair decides to banish Jenny from Manhattan. It seems like a huge decision and not one that’s enforceable, considering all Jenny’s friends and family are on the island, but it seems to work since Jenny disappears without a trace and doesn’t return until much later. Blair can make good on her threats, so it’s understandable Jenny stayed away — and it’s not surprising this was Blair’s reaction to what Jenny did.
1 Jenny: Slept With Chuck
What did Jenny do? Sleep with Chuck.
It was mostly Chuck’s fault, but it seriously hurt Blair since she couldn’t trust Chuck for a long time and tried to erase him from her life. She was unsuccessful and eventually forgave him, but it’s quite possibly the most hurt we see Blair in the whole series.
NEXT: Gossip Girl: 5 Worst Things Nate Did To Blair (& 5 Worst Blair Did To Him)
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Staci is a politics/psychology graduate from Scotland who went on to work in neither of those fields in the end. It happens. She’s a freelance writer who contributes to various Valnet sites and, when not working or travelling, spends most of her time watching horror movies, wasting an unreasonable amount of hours on the PS4 (despite being a Nintendo girl at heart), and trying to force her cat to love her.
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