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‘Sex and the City’: The Best One-Episode Boyfriends

Charlotte York, Miranda Hobbes, Carrie Bradshaw, and Samantha Jones tired out plenty of relationships during ‘Sex and the City’s’ six-season run. Most of those relationships didn’t last past a single episode. Charlotte, Carrie, and Miranda all passed on perfectly eligible men during their dating careers. So, who were the best of the discarded men the ‘Sex and the City’ ladies dated? That’s easy.

The ladies of Sex and the City did a ton of dating. Over six seasons Carrie Bradshaw, Miranda Hobbes, Samantha Jones, and Charlotte York collectively dated more than 90 men. Not all those men lasted more than an episode. In fact, most of the men who appeared on Sex and the City only spent a single episode with the girls. That doesn’t mean they were all bad, though. A few of those short-lived boyfriends seemed to have relationship potential. So, who were the best one-episode boyfriends?

Carrie Bradshaw dated Sean, an open-minded 20-something, for one episode in season 3 of Sex and the City 

Carrie had some seriously bad taste in men. Still, she managed to find a few good ones during her dating career. In season 3, Carrie dated a guy by the name of Sean. Sean was kind, caring, and progressive. Theoretically, he was the exact type of guy Carrie should have loved dating. Initially, his age was the only issue. They probably could have worked through that, but then he revealed that he was bisexual. His admission, which shouldn’t have been a big deal, was a huge deal for Carrie. 

Kristin Davis, Sarah Jessica Parker, Cynthia Nixon and Kim Cattrall pose for promotional photos for 'Sex and the City' season 3
The cast of ‘Sex and the City’ | HBO/Newsmakers

Carrie’s inability to deal with Sean’s sexuality led to her ditching him at his friends’ party when one of his friends prompted her to kiss a woman during a game of spin the bottle. Sean seemed like a good guy who any woman or man would be lucky to date. When you think about it, Carrie did him a favor. She was way too close-minded to get seriously involved with Sean. 

Charlotte York dumped Stephan for being too in touch with his feminine side 

Charlotte should have been jumping for joy when she met Stephan. The pastry chef was incredibly sweet and straightforward. He made his interest in Charlotte known and treated her well. Stephan was, technically, exactly what Charlotte claimed she wanted. Still, Charlotte managed to find something wrong with him. 

Kristin Davis as Charlotte York and Sarah Jessica Parker as Carrie Bradshsaw sitting on a bench in Central Park during a scene for 'Sex and the City' in 2001
Kristin Davis as Charlotte York and Sarah Jessica Parker as Carrie Bradshaw in ‘Sex and the City’ | Tom Kingston/WireImage

After spending a night together, Stephan decides to make Charlotte breakfast. His efforts were interrupted when the couple realized a mousetrap served its intended purpose. Both were terrified of the rodent, but Stephan’s inability to deal with it led Charlotte to break up with him, claiming that he was too “feminine” for her tastes. Charlotte was too judgmental to realize musophobia (or the fear of mice and rats) is not a “feminine” trait. Hundreds of thousands of people, including men, deal with the common phobia. Things probably turned out better for Stephan without Charlotte, though. He needed to be with a woman who didn’t adhere to such outdated gender roles. 

Miranda Hobbes let her own insecurities ruin a potential relationship with Detective Stevens 

Carrie’s bad karma after ruining Mr. Big’s marriage resulted in some good luck for Miranda. Carrie had her shoes stolen, and Miranda scored a date with an incredibly attractive detective. Detective Stevens seemed like a good guy. He was interested in Miranda and appeared to have eyes only for her, despite all eyes being on him. The two would have made a great couple if only Miranda didn’t let her insecurities ruin everything. 

Cynthia Nixon as Miranda Hobbes and Sarah Jessica Parker as Carrie Bradshaw chat while sitting on a bench in New York City during the filming of 'Sex and the City'
Miranda Hobbes and Carrie Bradshaw | RJ Capak/WireImage

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Miranda believed Detective Stevens was too good-looking to be interested in her. To mask her insecurities, she drank copiously during their date. Her drinking concerned the detective so much that he left her apartment quietly, but not before he suggested she seek help for her drinking. Miranda never saw him again.