Unfortunately for Me, Dan and Blair Had Gossip Girl’s Most Natural Romantic Build-Up
It is a difficult day for me personally because the evidence has become impossible to ignore: Dan Humphrey and Blair Waldorf were cute.
I said cute, not destined. Nobody needs to confiscate my Gossip Girl membership card yet. But after rewatching the show with slightly more developed judgment, I fear Dair may have had the most natural romantic build-up of them all.
Dan and Serena started beautifully. Their early relationship had everything a high-school romance needed: longing glances, dramatic misunderstandings and Dan behaving as though travelling from Brooklyn to Manhattan required a passport. Serena could escape the person everyone expected her to be, while Dan finally became visible to the girl he had admired from a distance.
Then the series spent years breaking them up, giving them new partners, turning them into stepsiblings and, for its grand finale, revealing that Dan was Gossip Girl. Serena learned that her boyfriend had secretly run the website that publicly humiliated her and her friends for years, then married him anyway. Even Penn Badgley admitted the reveal made no sense.
Serena did not simply marry Dan. She married the blog. Very modern of her, I suppose.
Chuck and Blair are harder to dismiss because their chemistry was absurd. One look across a ballroom and suddenly everyone forgot the last four restraining-order-worthy plotlines. They understood each other’s ambition, darkness and love of making a minor inconvenience everyone else’s emergency.
But chemistry cannot do all the administrative work in a relationship.
Chuck used Blair as collateral in his deal with Jack for the Empire Hotel. Later, he punched through glass near her and a shard cut her face, a scene the Los Angeles Times described as making their relationship look abusive. Those are not romantic complications. They are harm. The show repeatedly wrapped their worst moments in dramatic music, expensive coats and the promise that their love was simply too powerful to behave normally.
Then Dan and Blair appeared with the radical suggestion that two people could speak to each other before declaring themselves soulmates.
Their relationship grew through small, ordinary moments. They went to films, argued about art and competed for the same internship at W. An Entertainment Weekly recap from season four described them as two snobs who finally had something useful in common. They challenged each other because they respected the other person’s intelligence, even if Blair would rather have worn last season’s headband than admit it.
Their friendship also developed away from Serena and Chuck. Nobody arranged a grand gesture. There was no limousine, royal wedding or hotel negotiation. They simply kept choosing to spend time together.
The most convincing example is their Rosemary’s Baby movie night. They watch from separate places while talking on the phone, which is essentially a highly pretentious version of falling asleep on FaceTime. The writers allowed their friendship to grow slowly, and critics noticed that pacing at the time. Dan comforts Blair when she is hurt. Blair begins trusting him with the parts of herself that are not performing for an Upper East Side audience.
Even Leighton Meester recently revisited their first kiss and called the moment “cute,” specifically remembering the banter and secrecy leading up to it. I regret to inform the Chair committee that Queen B herself has entered evidence for the defence.
Dair were not a perfect couple. Dan remained judgmental, Blair continued treating Brooklyn like a communicable disease and their first attempt at sex was so disastrous that both of them briefly reconsidered the entire concept of attraction. Once they officially started dating, the writing became shakier. Dan’s insecurity about Chuck followed them everywhere, and Blair’s romantic feelings never received the same depth that Dan’s did.
Their build-up was better than their actual relationship. That distinction matters.
Dan and Blair worked because they became friends before the show remembered it was a teen drama and demanded another love triangle. He liked her mind before she liked him at all. She respected his talent before she could tolerate his hair. They discovered that beneath the money, insults and borough-based warfare, they genuinely enjoyed each other’s company.
Perhaps Chuck was Blair’s great love. Perhaps Serena was always Dan’s first choice. But Dair was the relationship that grew without needing destiny to explain it.
The real scandal was never their kiss. It was how much sense it made.