Some Gossip Girl couples should have never happened. Several pairings have fans scratching their heads, wondering what the show writers were even thinking!

While it’s obvious that Serena was always going to end up with Dan and Blair was always going to end up with Chuck, some of the other relationship pairings that went down truly made no sense at all.

Blair and Dan should have never been together.

After so much time spent building up Blair Waldorf’s hatred for Dan Humphrey, the fact that they ended up in a relationship is still mind-boggling to tons of Gossip Girl fans, even though the relationship was temporary.

Blair becoming the star of Dan’s novel was certainly an interesting plot twist in the show, but their relationship was extremely confusing to viewers across-the-board when it suddenly took root.

Blair spent so much time critiquing every single detail about Dan leading up to their super random romance. Her Upper East side vibe never quite meshed with his Brooklyn energy.

Jenny and Chuck should have never hooked up.

Jenny and Chuck never officially dated as boyfriend/girlfriend, but they did definitely hookup.

In fact, the night they hooked up was the night Jenny lost her virginity. This hookup was especially problematic for a slew of reasons.

First, Chuck tried to force himself on Jenny in an attempted sexual assault back in Season 1.

Second, Chuck had plans to propose to Blair the same evening he smashed Jenny, which meant his heart was clearly in a different place.

Chuck and Jenny only hooked up because they were both feeling depressed and lonely, but the entire situation was a hot mess.

Georgina and Dan should have never dated.

Why the hell did Dan ever date Georgina Sparks? When he first met her, she was pretending to be someone else and it was understandable that he was into her because he was being fooled by her lies.

But then later on, he dated her knowing exactly who she was!

It was extremely bizarre that Dan would give her a chance, knowing what a manipulative liar she was.

It definitely caused him some problems down the line when she pretended he was the father of her child knowing full well that he wasn’t.

Serena never should have given Trip van der Bilt a chance.

Serena dated around and had a lot of boyfriends along the way on Gossip Girl, but none of them were as bad as Trip van der Bilt.

First of all, he was MARRIED when they met. Serena was giving mistress side hoe energy with this one.

And then after getting into a car accident, he moved her body into the driver’s seat and abandoned her in the middle of the road.

He truly couldn’t have cared less if she lived or died.

Rufus and Ivy should have never gotten romantically involved.

The romantic pairing between Rufus and Ivy is arguably the worst Gossip Girl couple to ever exist.

It was disturbing seeing Rufus get so affectionate with someone who was the same age as his young adult children!

It was also extremely disturbing that he abandoned his relationship with Lily to pursue something so awkward, inappropriate, and gross with someone as mentally unstable as Ivy.

Which of these Gossip Girl relationships was the most cringeworthy in your eyes? Let us know in the comments!