When Gossip Girl started, Dan Humphrey (Penn Badgley) was just a lonely boy using thinly veiled code names like "Charlie Trout" to write fiction about his classmates. (And, apparently, nonfiction, too, as we'd later learn from the nonsensical identity reveal of our titular narrator.) There was no reason for Dan to end up dating any of the women he knew in high school, let alone marry one of them, but he did — unfortunately, it was the wrong one.
Gossip Girl's introduction of Dan and Blair's (Leighton Meester) relationship was a bold move. They'd spent ages being enemies before eventually interning at W magazine together. But against all odds, the Upper East Side princess and Brooklyn hipster had great chemistry.
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Blair and Dan brought out each other's intellectual sides — they could talk about classic movies and visit art exhibits together. When she was spending time with Dan, Blair was reading New York magazine and had NOVA documentaries in her Netflix queue! And aside from their intellectual similarities, Blair and Dan were always just twisted enough to work with each other. They're both manipulative, but neither of them was ever straight-up evil.
Dan also seemed capable of getting over his Serena (Blake Lively) hangup when he was with Blair (though she was never fully over Chuck, even when she was with Dan). He even wanted to help Blair raise her baby! They could have helped each other move on from unhealthy relationships, which would have been better for everyone; instead, they both ended up in questionable marriages. (Also, Dan and Serena have a half-sibling! Remember Scott?)
When Claire Willett made her (impressively well thought-out) Twitter thread about why Rachel and Joey should have been endgame on Friends, her argument was undercut by the fact that many of her pro-Joey arguments were really just digs at Ross. Ross was objectively terrible, but does that mean Rachel should be with Joey? I'm pointing this out because Blair and Dan should be together because they have a deep connection, not just because Chuck (Ed Westwick) is horrible — but it's worth noting, that, yes, Chuck is horrible.
Chuck tried to rape two people in the Gossip Girl pilot, something the show seemed to wish viewers would forget by the time his "fairytale" wedding to Blair rolled around. He also infamously "traded Blair for a hotel" by manipulating her into sleeping with his uncle Jack (it's a whole thing). That's definitely worse than being Gossip Girl.
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Plus, on a not-insignificant note, Dan and Blair being together would leave room for Rufus (Matthew Settle) and Lily (Kelly Rutherford) to be with each other. These two have a history, okay? There's so much chemistry between them in each of their scenes, but they abandoned their obvious love for each other so that their kids could be together. That's true self-sacrifice, but it's also messed up! They were in love first! And Rufus' apparent endgame relationship with Lisa Loeb was baffling and out of nowhere — Lily is his true love. Clearly.
Dair for life, end of story.
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