Sex And The City: Carrie’s 10 Worst Flings, Ranked

For six seasons, the ladies of Sex and the City provided their fans with complex relationships, laughs, heartbreak, and some really good fashion choices. It also provided some of the best scenes that will live rent-free in fans’ heads for years to come, and while some involve the best relationships in the series, there are others that feature some of Carrie Bradshaw’s more questionable flings.

Some of the best episodes involve these Mr. Wrongs, and the situations Carrie Bradshaw (Sarah Jessica Parker) gets into with them. Everyone has their own quirks, but these guys are on a whole different level.

Carrie Bradshaw has had a lot of dates through the Sex and the City series, but in the episode, “The Freak Show,” she ponders the idea that all men in the city might be “freaks.” Carrie goes on a trio of dates throughout the episode, and one of them happens to be a perfectly capable man who decides to steal things for the sake of it. This might be giving insight into a deeper issue and Carrie catches wind of it.

She decides that everyone might have a little “freak” in them after she goes through another date’s apartment looking for a flaw that isn’t there.

Even though Carrie has a date with fellow writer, Jack Berger, she tries her hand at dating “simultaneously,” after getting advice from the girls. She meets Willie Applegate, played by Wallace Langham, a seemingly nice man, but his nerves and obsession with a possible stye in his eye have him acting extremely awkward.

What follows is a string of uncomfortable events, such as Wallace getting balsamic vinegar in his eye and a pigeon landing on his head. It’s safe to say this is one of Carrie’s clumsiest dates. At this point, Carrie might be better off dating someone who she really wants to date, instead of putting herself out there just so she can date multiple people at the same time.

While doing a bit of cardio, also known as “shopping” for Carrie, she runs into her friend Amalita and her new boyfriend. Amalita’s life is extravagant with trips and rich men, and while she’s in town, she invites her to dinner. Later on, Carrie meets an architect named Gillies, who she is immediately attracted to. She decides to spend the night with him at his hotel, and after a fun-filled night, she wakes up to find Gilles has left and a stack of money is left instead.

Apparently, Amalita is a sex worker and Gilles assumed that Carrie was too. It might’ve been a miscommunication, but it was still incredibly shocking for Carrie to wake up to that.

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