Carrie Bradshaw writes about relationships for a living, so it comes as no surprise that her own love life is difficult to keep track of. Over the course of Sex and the City, she has numerous flings and a handful of serious relationships, with each lover bringing his own challenges that Carrie must overcome. Although only one of these relationships works out in the end, the boyfriends and flings that Carrie has on the show all teach her something different about love and she brings all that information together in her columns.
The main romantic players in Carrie’s life are John James ‘Big’ Preston and Aidan Shaw, followed by Jack Berger and Aleksandr Petrovsky. In between these men, she also has a few shorter flings with the likes of Bill Kelley and Ray King. Check out Carrie’s relationship timeline below!
15 Carrie’s Relationship With Kurt Harrington Was Purely Physical
In the pilot episode, Carrie tests out the theory that women can have sex like men. She meets up with Kurt, who is later identified as her “sleeping” buddy. Carrie learns that sleeping with men the way they often sleep with women doesn’t leave her feeling fulfilled. Kurt returns later in the season, but this relationship has no potential outside the bedroom.
14 She First Dates Big In Season 1
Carrie meets Big in the pilot and eventually starts dating him for the first time a few episodes later. From the very beginning, Big is emotionally unavailable and refuses to be what Carrie needs him to be. Their relationship ends when she finally catches on that he’s not going to be emotionally available for her anytime soon.
13 Carrie Sabotages Her Potential Relationship With The Flawless Ben
Over the course of the series, Carrie dates a lot of questionable guys. Ben is one of the few who is perfectly fine. In this instance, it’s actually Carrie who has the problem. She’s so paranoid that there’s something wrong with him that she snoops through his private belongings in his home when he’s not there.
12 Carrie Gets Back Together With Big In Season 2
Despite having decided Big was too emotionally unavailable for her, Carrie starts seeing him again in the second season. This time, their relationship comes to a screeching halt when Big announces that he’s going to Paris indefinitely and he wasn’t going to mention it to Carrie until the last minute.
11 After Breaking Up With Big Again, Carrie Dates Author Vaughn Wysel
After Carrie moves on from the heartache that Big causes her again, she begins dating Vaughn Wysel, another writer. Vaughn has a few problems in the bedroom, but Carrie is reluctant to break up with him because she gets along with his family, and particularly his mother, so well. But he doesn’t end up sticking around for very long!
10 She Dates Bill Kelley In Season 3
At the beginning of the third season, Carrie starts dating congressman Bill Kelley, who we find out has a few fetishes that Carrie isn’t cool with. He dumps her when she tells him that she’s not comfortable playing out his fantasies, but she gets him back by throwing shade at him in her column.
9 Carrie Only Dates Sean Briefly Before Realizing She’s Not Easy-Going Enough
Sean doesn’t last very long in the series, but he’s one of the most memorable flings that Carrie has. Carrie soon decides that she’s not interested in pursuing a relationship with Sean because, although he is fun and easy-going, he is bisexual, which she realizes is a deal-breaker for her.
8 Aidan Comes Into Carrie’s Life In Season 3
Aidan first comes into Carrie’s life in Season 3 and ends up leaving the biggest impact, after Big of course. She decides to give up smoking for him (although she ends up smoking in secret), and freaks out because the relationship goes too smoothly and he doesn’t want to be intimate with her straight away.
7 The Disastrous Carrie-Big Affair Sends Aidan Packing
Carrie’s relationship with Aidan disintegrates when she has an affair with Big, who’s now married to Natasha. They manage to keep their renewed relationship a secret in the beginning, but soon Natasha catches Carrie in her apartment and Carrie decides to fess up to Aidan (on Charlotte’s wedding day no less).
6 Big Is Jealous When Carrie Dates Ray King
After Aidan leaves her and her relationship with Big ends (for the time being), Carrie starts seeing a jazz musician called Ray King. She first meets him when she’s out with Big as a friend, leaving him feeling a little jealous. Ultimately, Ray has too much energy for Carrie, who can’t deal with his ADD.
