While Jim initially came across as a decent enough guy, it was soon revealed that Carrie broke up with him for a good reason โ he's awful. Carrie repeatedly warned Miranda he was not a good guy and that they ended on bad terms.
However, Miranda tried to convince Carrie that maybe he'd changed and that they should all get together. While the three grabbed drinks, Jim began hurling digs at Carrie, saying she "walked all over him" while they were in a relationship, among other pointed insults. Carrie slept with Kurt Harrington in the first episode of the series to prove that women can "have sex like men" without emotional attachment. It's clear they'd been sleeping together on and off for years, but no relationship had ever formed.
Aw, Willie. I'm sure he was a sweet guy, but that date couldn't have gone worse. Between the horrible pick of a date spot, knocking the table over, and going on and on about his stye, it's not surprising that he and Carrie didn't go any further than the first date.
Howie Halberstein initially came across as funny, charming, and good-looking. However, Carrie was only looking for a "fling" while he was in town for Harry and Charlotte's wedding, and he apparently was looking for more.
After a night of horrible sex, causing Carrie to be hunched over in pain the next day, she told him she was just looking for a bit of fun. He completely lost his head, drunkenly called her a b in his best man's speech, and said she "used him for sex" in front of everyone at the wedding. Wade made Carrie feel like she was in high school again, between his old Styx albums and his affinity for a Razor scooter.
