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What if Blair Ended up with Dan Instead of Chuck?

Michelle Lee-Ann
3 min readOct 29, 2020

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Could a Waldorf really be with someone from Brooklyn?

photo from Canva

We all know that Blair and Chuck’s lovestory is one for the ages. We also know about Dan’s Gatsby-inspired obsession with Serena. What we didn’t know, at least in the beginning of the show, was that Dan and Blair would end up together…and happily so. So, what if they actually did end up together? As in, married with little designer clad writers running around? What would that look like? What would have happened if she had followed him to Rome, instead of falling into Chuck’s arms?

Blair would be intellectually happy

While Chuck isn’t stupid, Dan and Blair would often have intellectual conversations, even trying their hand at hosting their own salon when they broke out as a couple. Chuck and Blair were madly, head-over-heels, story-book romance in love with one another. With Dan? She was happy, content. They’d spend hours, not having Harlequin worthy sex, but talking. Watching obscure movies together, dissecting said movies, going to the theatre, to museums. They would feed off of one another’s love for great literature, art, and movies. At first I was horrified at Blair and Dan, but then it made more sense as the episodes went on. They’re similar in their intellectual mindset, if not their upbringing and wardrobe choices.

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Michelle Lee-Ann
Michelle Lee-Ann

Written by Michelle Lee-Ann

Recently published kid's book author, lover of all things Karl Lagerfeld, Golden Girls enthusiast, and finds happiness in books from Hemingway to Harlequin.

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