Top 10 Memorable Carrie Bradshaw Boyfriends
#10: Ray King
Aidan vs. Big: The Battle of Carrie Bradshaw's Boyfriends
While out on a date that isn’t really a date with Mr. Big, Carrie meets “the jazz man”, Ray King, at a club where he’s performing. What ensues is the most awkward cab ride of all time, as Ray makes it clear that he’s interested in Carrie even though Big is there. The most memorable part of their interaction is, of course, the incredible sex that they end up having, even though the two don’t actually have much in common - Carrie doesn’t care for jazz and he seems to be obsessed with it. In the end, she diagnoses him with attention deficit disorder and we never hear from him again, but he certainly made a lasting impression!
#9: Wade Adams
In a fan favorite season three episode, all four of the ladies are confronted with issues about youth. Carrie meets Wade at the comic book store where he works and eventually goes to see his gorgeous apartment with incredible views. How does Comic Book Guy afford such a nice pad? Well, he still lives with his parents, of course! The two end up having a youthful romance that involves smoking a lot of weed and throwing fried chicken off the balcony. He does something unforgivable though when he blames Carrie for bringing drugs into the house. At least she gets to take them as a parting gift!
#8: Sean
While some of the progressive ideas presented in “Sex and the City” still hold up today, other episodes admittedly make us cringe in horror at what’s going on on-screen. This is perhaps one of the worst ones, where Carrie dates a bisexual man, and the group tears into the idea of bisexuality, delivering some lines about it that surely everyone involved in the show regrets. Sean is a totally great and nice guy, but things don’t work out between him and Carrie because she is of a generation that apparently just can’t fathom such things. Her loss!
#7: Vaughn Wysel
When Carrie and Vaughn first got together, viewers were on the edge of their seats, thinking perhaps he was the one - he was even a writer! It seemed like they were perfect for each other, down to his quirky New York family who quickly welcomed Carrie with open arms. Unfortunately though, all that glitters is not gold and these two had problems in the bedroom. His performance issues wouldn’t have been the end of the world if Vaughn was willing to keep an open line of communication about them, but unfortunately, he’s not. In the end it didn’t work out, but we’d like to imagine that Carrie still kept in touch with his mom!
#6: Jeremy
By the show’s sixth season, Carrie had been through a lot of dates, some good and some awful. So it made sense that she was ready to retread some old ground and revisit a relationship that had ended long ago. David Duchovny plays Jeremy, a guy that Carrie dated in high school who she reconnects with many years later. Everything seems great - the only problem is that he’s actually undergoing treatment at a mental health facility. With years of perspective, and the changing social climate, this honestly seems like far less of a dealbreaker than it did when the show aired, especially considering how great Jeremy was.
#5: Bill Kelley
Top 10 Times Bill Hader Broke The SNL Cast
We never exactly imagined Carrie dating a politician, but when Carrie meets Bill Kelley at a charity event for the New York Fire Department, their chemistry is immediately obvious. Their courtship ended up spanning two episodes, which is pretty serious for the show, and Carrie easily slipped into the role of political partner. In the end though, Bill’s backwards views on Carrie’s sex column were totally incongruous with the fact that he was into golden showers. In retrospect, this has an even bigger ick factor than when we first saw it - that level of hypocrisy has only gotten uglier with age.
#4: Aleksandr Petrovsky
Now we’re down to the four men that Carrie dates most seriously throughout the show’s run. She meets artist Aleksandr Petrovsky half-way through the final season, and their relationship immediately gets serious, even though it’s obvious to pretty much everyone that they aren’t exactly a great match. He heartlessly kills mice, he is unsympathetic about Samantha’s cancer, and in one of the most memorable moments of the series, he even slaps Carrie in anger. While this relationship was significant because it ultimately brought Carrie and Big together, it’s clear in hindsight that it never could have worked.
#3: Jack Berger
Top 10 Times Samurai Jack Went Beast Mode
When Carrie met Berger and they started dating, viewers were led to believe that this might be it. He was a witty and sharp writer, just like she was, and they seemed to have tons in common. As both she and the viewer got to know him, however, the perfect image started to crumble. He was jealous of Carrie’s professional success, which is definitely not a good look, and let’s not forget the time he picked a fight with Carrie over a scrunchie. No matter what though, Jack Berger will go down in TV history as the guy who broke up with Carrie Bradshaw on a post-it.
#2: Aidan Shaw
What If Carrie Had Stayed with Aidan?
Ah Aidan, the guy that half of us totally wanted Carrie to end up with. What is there not to like about this charmer? He’s sweet, he’s sensitive, he’s a dog lover, he hates drama and he even managed to forgive Carrie for having an affair with her ex. Really, the only thing wrong with this relationship was Carrie! Obviously the two weren’t meant to be because she just wasn’t into it, but they shared many memorable moments from their very first date to both of their devastating breakups. And the fight they have over closet space? It remains one of the best scenes of the entire show. Before we unveil our top pick, here are a few honorable mentions. Patrick Casey Keith Travers Seth Sam Howie Halberstein
#1: Mr. Big
Top 10 Reasons Carrie Bradshaw Was the WORST
Of course, our number one spot had to go to Mr. Big. Not because he is our favorite necessarily, but because the show simply wouldn’t be the same without him. Carrie meets Big in the very first episode of “Sex and the City” and her relationship with him spans the entire series and beyond. Yes, he’s emotionally unavailable and constantly jerks Carrie around, but she clearly loves him and will do pretty much anything to make it work with him. We may not love him as much as she does, but you can’t deny their chemistry and the fact that in one way or another, they were meant to be.
