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A Ranking Of The Serious* Relationships Of Sex And The City

*serious = appeared in more than one episode. Like, of course not all of these will be serious, but neither are all relationships in life, right?

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17. Kevin

HBO

Actor: David Lansbury

Partnered with: Miranda

First episode: S2E14, “The Awful Truth”

Number of Appearances: 2

Let's just get this asshole out of the way. Technically, Kevin and Miranda "dated" for only one episode, but he reappears seasons later when she calls to inform him she has chlamydia. Turns out, he already has it, and never bothered to tell her! Plus, when they dated, he was a miserable prick. Boo.

16. Bill Kelley

HBO

Actor: John Slattery

Partnered with: Carrie

First episode: S3E1, “Where There's Smoke...”

Number of Appearances: 2

One of the more memorable breakups of the show, Bill started out alright (for a politician) when he agreed to take it slow with a heartbroken Carrie. However, once Bill began showing his true ~colors~ (namely, the color yellow - oops!), the relationship fizzled. But it was Bill's problem with Carrie's column that truly did it in for this guy. Enjoy the showers!

15. Ray King

HBO

Actor: Craig Bierko

Partnered with: Carrie

First episode: S4E3, “Defining Moments”

Number of Appearances: 2

Not to knock ADHD, as it was super unfair of Carrie to write this guy off due to his behavioral disorder, but Ray was super annoying. He was never smooth except when he played jazz, and the show never really sold their chemistry. One big gimmick of a relationship, TBH, though he gets points ditching Carrie for a banjo.

14. James

HBO

Actor: James Goodwin

Partnered with: Samantha

First episode: S1E12, “Come All Ye Faithful”

Number of Appearances: 3

Ah, James. So much promise, one major shortcoming. Samantha was happy with him for a while - long enough to last 3 episodes! - but the tiny elephant in the room eventually took over. A positive: the scene when she ditched him is one of the most iconic counseling scenes of all time. We all need a big dick, eh?

13. Walker Lewis

HBO

Actor: Robert John Burke

Partnered with: Miranda

First episode: S4E13, “The Good Fight”

Number of Appearances: 2

One of the two Miranda relationships that we all wish could have happened (sorry Steve). Walker was successful and sexy, plus he gifted Miranda with seriously hot sex before she had a child. And who could blame him for freaking out when he hears Brady crying while he and Miranda had sex? Wish we could have seen more of you, Walker.

12. Jack Berger

HBO

Actor: Ron Livingston

Partnered with: Carrie

First episode: S5E5, “Plus One is the Loneliest Number”

Number of Appearances: 8

Yep, this guy is worse than Skipper AND The Russian. Berger is whiny, jealous, and obnoxious, even from the beginning, when he leads Carrie on before dropping the girlfriend bomb. What was likable about this guy? And then, when they do date, he has the audacity to try to drop bad advice on Carrie's friends? And they have awkward, bad sex? And he has "big man" issues with the motorcycle and Carrie's successes? Girl, you should ditched this one and his baggage way before you did.

11. Skipper Johnston

HBO

Actor: Ben Weber

Partnered with: Miranda

First episode: S1E1, “Sex and the City”

Number of Appearances: 7

Sweet, naive, annoying Skipper. What a guy. We meet him in episode 1, as the not-cautiously optimistic geek who pursues Miranda. We see him a few more times, as the still-optimistic geek who breaks up with a girl while he's inside her to return to Miranda. Lovable, goofy, and ultimately exhausting. Sorry, but this wasn't one of the Miranda relationships to root for.

10. Aleksandr Petrovsky

HBO

Actor: Mikhail Baryshnikov

Partnered with: Carrie

First episode: S6E12, “The One”

Number of Appearances: 9

UGHHHHHhhhhh this guy. It's a bit of a shame that Baryshnikov had to be so cold, one-dimensional and detached, which are some truly ugly Russian stereotypes. Aleksandr never considered what Carrie wanted, he didn't bother trying to understand her, and when she ultimately changed her life for him he just couldn't be bothered to make any changes for her. Groan.

9. Maria Diego Reyes

HBO

Actor: Sônia Braga

Partnered with: Samantha

First episode: S4E3, “Defining Moments”

Number of Appearances: 3

It was easy to root for this relationship at the start, especially after Samantha's friends were a little (extremely) judgmental of her for experimenting with a woman. In this relationship we saw a different side to Samantha, watching her attempt monogamy and search for something outside her comfort zone. Ultimately, the flame died out, and Samantha had to (literally) sweep up the pieces afterwards.

8. Trey McDougal

HBO

Actor: Kyle MacLachlan

Partnered with: Charlotte

First episode: S3E7, “Drama Queens”

Number of Appearances: 23

Finally, we reach one of Charlotte's two (yes, that's really it) repeat relationships throughout the series. At the start, Trey was the whole package - until Charlotte discovered, in an untimely fashion, that this package came with some added baggage. This was one of the first SATC relationships that truly ran its course, and while Trey clearly loved and was good to Charlotte, by the end you just wanted him gone.

7. Richard Wright

HBO

Actor: James Rennar

Partnered with: Samantha

First episode: S4E10, “Belles of the Balls”

Number of Appearances: 12

Okay, so Richard had his flaws (sushi, anyone?). But, at least at the beginning, Richard worked harder than any man to convince Samantha to give him a shot. He loved her and cared for her, even if he couldn't keep his tongue to himself. Plus, he's pretty nice to look at, even though Samantha was able to overlook that and everything else for the sake of her own happiness. Always the inspiration.

6. Dr. Robert Leeds

Actor: Blair Underwood

Partnered with: Miranda

First episode: S6E9, “A Woman's Right to Shoes”

Number of Appearances: 5

Phew, what a fine specimen. Robert was not only crazy hot (and we got to see his butt!!), but he was also a DOCTOR and super-sweet to Miranda. This was the other Miranda relationship we were rooting for. If it weren't for her baby daddy, it's not hard to think these two would have gone further. But the only thing wrong with Robert, in the end, was that he wasn't Steve. Sad!

5. Aidan Shaw

Actor: John Corbett

Partnered with: Carrie

First episode: S3E5, “No Ifs, Ands, or Butts”

Number of Appearances: 22

Oooookay, so there will be some flack for this, but someone had to be #5. Aidan was sweet yet rugged, a guys-guy yet sensitive. But did he ever truly understand Carrie? He tried, painfully hard at times, but he never really got her. And, hot take coming through: he was a little boring and lacked a critical awareness of the relationship he was in. He was comfortable, which can be great, but if he and Carrie stayed together longer the thrill would be gone. And Carrie lives for the thrill. That's why the painful cheating arc needed to happen, to prove that Aidan was never the right fit for Carrie, and was the last one to figure that out for himself. Sorry, Aidan. We still love you.

4. Steve Brady

HBO

Actor: David Eigenberg

Partnered with: Miranda

First episode: S2E8, “The Man, The Myth, The Viagra”

Number of Appearances: 41

Aw, Steve! He was such a goober, and couldn't be more polar opposite to Miranda. But their relationship was realistic - probably the most realistic of all the serious relationships on this show. Their story took natural highs and lows, with their breakups being about their differences and changes that they each needed to make for the other. Plus, they were excellent parents to Brady even when they were separated, which is saying something. After all the shenanigans of the other storylines on this show, Steve and Miranda were refreshing and real to watch. All hail!

3. John James Preston (Mr. Big)

HBO

Actor: Chris Noth

Partnered with: Carrie

First episode: S1E1, “Sex and the City”

Number of Appearances: 41

Whatever, haters. You have to admit, this show would be nothing without Big. The drama, the dips, the dashing looks - this guy was nearly as pivotal to SATC as the girls themselves. But he doesn't get #1 status because at his worst, Big was a jerk with some serious emotional unavailability issues and he overall could have treated Carrie better. But once he tapped into what he really wanted, there was no denying he was the one for Carrie. He understood her, and that's why nobody else - sorry not sorry, Aidan - was right for her in the end.

2. Smith Jerrod

HBO

Actor: Jason Lewis

Partnered with: Samantha

First episode: S6E2, “Great Sexpectations”

Number of Appearances: 18

For a long time, Smith would have topped this list. He's impossibly attractive, with a heart as big as his downstairs (presumably) and a maturity that surprised even Samantha, a woman surprised by nothing. With all its flaws, the final season of Sex and the City and the following movie gave Smith and Samantha the story they both deserved. Their breakup was 100% the most devastating of all, considering all these two had been through. The sole reason he isn't #1 was because for his first few episodes of season 6, Smith was a pretty flat character and didn't click with Samantha. She seemed bored with him, until all the mucky Richard stuff. Otherwise, this man is flawless.

1. Harry Goldenblatt

HBO

Actor: Evan Handler

Partnered with: Charlotte

First episode: S5E6, “Critical Condition”

Number of Appearances: 18

So sue me, I like an underdog. When it comes to the guys on this show, and especially when it comes to Charlotte, Harry was certainly an underdog. But the show let him prove himself, and he ended up being everything Charlotte needed and deserved. Plus, he shaved his back for her! And he put her needs first and foremost with all the baby stuff! And he came back to her after she said those horrible things about him! Harry wasn't Charlotte's fantasy, but he ended up being the perfect man for her, and the perfect man in this series. Fin.

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