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Carrie Bradshaw’s love life is active again, or so it looks like it will be in season 2 of And Just Like That…, the HBO Max reboot of Sex and the City. It won’t be the first time fans watch the sex columnist date in New York City. For six seasons, fans watched Carrie date a nearly neverending line of men before settling down with Mr. Big for good. While some of those men were nice and felt like a good fit, there were just as many misses. These three boyfriends were never going to make Carrie Bradshaw happy. 

Wade Adams was an awful fit for the sex columnist

If we are looking for Carrie’s most mismatched relationship partners, we need to look no further than Wade Adams. Carrie met Wade in season 3 of Sex and the City and struck up a fun little romance. What started fun turned pretty strange when it became obvious that Wade wasn’t a grown man trying to make his entrepreneurial dreams come true; he was a man who had failed to leave the nest. 

Sarah Jessica Parker spirit animal
Sarah Jessica Parker on the set of ‘And Just Like That…’ in July 2021 in New York City | James Devaney/GC Images

Wade, a comic book store owner, was incredibly immature and had absolutely no interest in growing up anytime soon. He lived with his parents, spent his money on marijuana, and happily let his parents take care of all of his needs. Within just a couple of dates, Carrie began to turn into a teenager herself before reality finally caught up with her. Carrie left the relationship quickly, but we still consider Wade Adams, her most mismatched paramour. 

Carrie Bradshaw tried to turn a hookup into a boyfriend and failed 

It seems unlikely that you could know someone for years without realizing they were truly the most boring human being alive. That’s exactly what happened when Carrie attempted to turn a regular hookup into a potential boyfriend, though.  

Dean Winters wears a black jacket at the premiere of Knockaround Guys' in New York City
Dean Winters | Dimitrios Kambouris/WireImage

In season 2, Carrie decided to turn her hookup, John McFadden, into a potential love interest. John wasn’t particularly keen on the idea but went along with a date anyway. The duo had one dinner together. That’s all Carrie needed to realize that John was boring. That one dinner was painful enough for us to realize John was one of Carrie’s most mismatched lovers. We never saw him again. 

Dr. Bradley Meego was kind and stable, but a complete mismatch for Carrie Bradshaw

Carrie might have dated a lot of different men, but one type of man confused her more than others. Carrie had a really hard time when it came to dating stable, well-adjusted men. In season 2, Carrie met a man named Bradley Meego at a book signing. Bradley was “good on paper.” Carrie acquiesced that he seemed perfect, but something kept her from getting involved. While Carrie said she didn’t know what made her shy away from the cute doctor with a house in the Hamptons, we think we know. 

Patrick Breen appars at the 16th Annual GLAAD Media Awards. Breen portrayed Dr. Bradley Meego in one episode of 'Sex and the City'
Patrick Breen | Jeffrey Mayer/WireImage
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Dr. Bradley Meego was too uncomplicated, stable, and kind for Carrie. Carrie seemingly ghosted him, but that was her loss and Dr. Bradley Meego’s gain. The couple was terribly mismatched. We theorize that the seemingly well-adjusted doctor wouldn’t have been able to keep up with Carrie’s more chaotic lifestyle.