Ranking The 107 Men Of “Sex And The City”

Carrie, Miranda, Charlotte, and Samantha dated and slept with more than 100 different men over six seasons. Here’s a ranking of all of them based on dateability: the good, the bad, and The Turtle.

107. The Turtle (Tim Wheeler)

HBO

Paired with: Samantha
First appearance: Season 1, Episode 9, “The Turtle and the Hare”
The verdict: The Turtle was Samantha’s PR project. She was determined to turn one of New York’s richest but most repugnant bachelors into someone dateable. And it worked — so well, in fact, that he decided to move onto someone new.

106. Len Schneider (Robert Lupone)

HBO

Paired with: Samantha
First appearance: Season 3, Episode 8, “The Big Time”
The verdict: Unctuous Len was an act of desperation, someone Samantha turned to when she thought she was going through menopause. Once she got her period, she bailed.

105. William (Robert Montano)

HBO

Paired with: Samantha
First appearance: Season 2, Episode 4, “They Shoot Single People, Don’t They?”
The verdict: William was a total sleaze who promised to take Samantha on expensive vacations and turned out to be full of shit. But that should have been immediately apparent based on that smile alone.

104. Buster (James Urbaniak)

HBO

Paired with: Charlotte
First appearance: Season 2, Episode 12, “La Douleur Exquise!”
The verdict: Buster and Charlotte didn’t really date — he just let her try on some very expensive shoes for the chance to be close to her feet. It was a fine arrangement for a while, until it got too creepy.

103. Ed (Bill McHugh)

HBO

Paired with: Samantha
First appearance: Season 2, Episode 8, “The Man, The Myth, The Viagra”
The verdict: Ed was just too old for Samantha. Sure, he lavished her with gifts, and — thanks to his Viagra — was able to perform. But still.

102. Kevin (David Lansbury)

HBO

Paired with: Miranda
First appearance: Season 2, Episode 14, “The Awful Truth”
The verdict: Miranda thought Kevin was a little bossy and uptight, but his combativeness was part of being a high-powered attorney. It turned out he was really just an asshole and super unpleasant to be around.

101. Jim (Dominic Fumusa)

HBO

Paired with: Miranda
First appearance: Season 3, Episode 16, “Frenemies”
The verdict: Jim was actually Carrie’s ex, but he turned out to be another asshole Miranda dated as well. Even though Carrie warned Miranda about how awful Jim was, she didn’t see the extent of his dickishness until he started attacking Carrie in front of her.

100. Dominic (John Shea)

HBO

Paired with: Samantha
First appearance: Season 2, Episode 11, “Evolution”
The verdict: Samantha really wanted to teach Dominic a lesson for all the times he had screwed her over. Naturally, that backfired and he ended up screwing her over again. Best laid plans.

99. Jon (Kohl Sudduth)

HBO

Paired with: Samantha
First appearance: Season 1, Episode 4, “Valley of the Twenty-Something Guys”
The verdict: Samantha’s twentysomething wasn’t nearly as exciting as Carrie’s (who lands in a far better position on this list). To top it off, he was dumb enough to comment on her barely existent neck wrinkles, which made Samantha feel old. What a waste.

98. Kevin (David Lee Russek)

HBO

Paired with: Charlotte
First appearance: Season 1, Episode 11, “The Drought”
The verdict: Kevin seemed like a catch, but he couldn’t have sex. Like, at all. That’s because he was heavily medicated for anger management problems, so even if he went off the Prozac, he’d have some issues. Such a handsome guy, but a lose-lose situation.

97. Luke/Manhattan Guy (David Wike)

HBO

Paired with: Miranda
First appearance: Season 2, Episode 3, “The Freak Show”
The verdict: Things were doomed from the start with Luke, who quickly outed himself as Manhattan Guy and sneered at Miranda’s trip to Connecticut. Yes, Manhattan is a great place, but it’s not the only place on Earth.

96. Kurt Harrington (Bill Sage)

HBO

Paired with: Carrie
First appearance: Season 1, Episode 1, “Sex and the City”
The verdict: Kurt was the impetus for the whole “have sex like a man” philosophy that began the series, as Carrie decided to treat a past mistake like a piece of meat. So, yeah, Kurt’s one defining characteristic is that he’s a douche.

95. Mr. Cocky (John Enos)

HBO

Paired with: Samantha
First appearance: Season 2, Episode 18, “Ex and the City”
The verdict: Too big for Samantha, and that’s saying something. Mr. Cocky’s confidence was sort of charming, but since sex with him was literally impossible, it was all kind of lost on Sam.

94. Brad (Ross Gibby)

HBO

Paired with: Charlotte
First appearance: Season 3, Episode 5, “No Ifs, Ands, or Butts”
The verdict: Brad was a horrible kisser. Just the worst. And while he may have had good qualities outside of that, the impression he left was of someone who couldn’t figure out how to make out without licking Charlotte’s face. Sorry, Brad.

93. Siddhartha (Anthony DeSando)

HBO

Paired with: Samantha
First appearance: Season 1, Episode 11, “The Drought”
The verdict: That whole tantric celibacy thing would be fun for a while, but come on. Siddhartha absolutely refused to have sex with Samantha, even when he got an erection in her presence. Way too frustrating.

92. Greg (Anson Mount)

HBO

Paired with: Charlotte
First appearance: Season 2, Episode 17, “Twenty-Something Girls vs. Thirty-something Women”
The verdict: Greg was so young that Charlotte felt compelled to lie about her age. He was totally cute, but he also gave her crabs. So, probably not worth it.

91. Sam Jones (Jacob Pitts)

HBO

Paired with: Samantha
First appearance: Season 3, Episode 17, “What Goes Around Comes Around”
The verdict: Aside from the narcissistic thrill Samantha got from sleeping with someone also named Sam Jones — and taking his virginity! — Sam was just too young and needy to be taken seriously.

90. Harrison (Marc Kudisch)

HBO

Paired with: Samantha
First appearance: Season 2, Episode 3, “The Freak Show”
The verdict: Hey, to each his own. But Harrison’s instant transition from lawyer to BDSM freak was a little much for Samantha to take. Not to mention presumptuous!

89. Thomas John Anderson (John Benjamin Hickey)

HBO

Paired with: Miranda
First appearance: Season 1, Episode 12, “Oh Come All Ye Faithful”
The verdict: Talk about issues. Thomas John Anderson may have been a brilliant playwright, but his sexual hang-ups were too much to endure. When Miranda called him on his Catholic guilt, Thomas lost it and kicked her out.

88. Bram Walker (Kevin J. Flynn)

HBO

Paired with: Charlotte
First appearance: Season 2, Episode 16, “Was It Good for You?”
The verdict: Bram fell asleep during sex. Yeah, he had clocked in long hours at work, but regardless, that was totally unacceptable.

87. Shmuel (Glenn Fleshler)

HBO

Paired with: Charlotte
First appearance: Season 1, Episode 6, “Secret Sex”
The verdict: Apparently, Charlotte had a great time with this Hassidic folk artist, but they were from two different worlds, and neither would tell anyone about the other. If only he’d known Charlotte would eventually convert.

86. Dick Cranwell (Michael De Vries)

HBO

Paired with: Samantha
First appearance: Season 2, Episode 5, “Four Women and a Funeral”
The verdict: Samantha fooled around with this rich philanthropist in exchange for a donation — a noble cause, until his wife walked in and temporarily ruined Sam’s reputation.

85. Barkley (Gabriel Macht)

HBO

Paired with: Samantha
First appearance: Season 1, Episode 2, “Models and Mortals”
The verdict: Grossly obsessed with models and a total sleaze, Barkley gets points for being a sexy artist. He made Samantha feel lousy, however, when he refused to film her during sex.

84. Harvey Terkell (James McCauley)

HBO

Paired with: Samantha
First appearance: Season 2, Episode 10, “The Caste System”
The verdict: Ah, the thrills of sleeping with a man who has his own servant! Unfortunately, Harvey’s servant was very much in love with Harvey and treated Samantha like shit because of it. So much for being pampered.

83. Ned (Kurt Deutsch)

HBO

Paired with: Charlotte
First appearance: Season 2, Episode 5, “Four Women and a Funeral”
The verdict: Sweet, sensitive Ned was just the kind of open-hearted guy Charlotte was looking for. But the guy had baggage, namely a very recently deceased wife. And he was looking for comfort with a variety of women, not just Charlotte.

82. Doug (Jim Gaffigan)

HBO

Paired with: Miranda
First appearance: Season 4, Episode 3, “Defining Moments”
The verdict: Doug’s major flaw was that he insisted on no bathroom privacy. Not a big deal when he just wanted to pee next to Miranda, but as soon as he pooped in her presence, Doug was a goner.

81. Derek aka The Bone (Andrea Boccaletti)

HBO

Paired with: Carrie
First appearance: Season 1, Episode 2, “Models and Mortals”
The verdict: OK, so it turns out The Bone wasn’t really interested in boning Carrie — he just wanted to talk. And while that’s obviously disappointing, it’s nice to know there’s a thoughtful guy to go with that face.

80. Lew (Sam Seder)

HBO

Paired with: Miranda
First appearance: Season 3, Episode 14, “Sex and Another City”
The verdict: While he wasn’t the miserable guy Miranda remembered, Lew still had issues. For one, he was way too L.A. for Miranda to deal with. Also, he had a pretty serious eating disorder.

79. Lance Bloom (James Villemaire)

HBO

Paired with: Miranda
First appearance: Season 3, Episode 15, “Hot Child in the City”
The verdict: Love Miranda, love her age-inappropriate braces. Yes, she looked ridiculous with food stuck in them, but couldn’t Lance have given her a break? He seemed like a nice guy otherwise.

78. Jack (Will Arnett)

HBO

Paired with: Miranda
First appearance: Season 2, Episode 12, “La Douleur Exquise!”
The verdict: Sexy and adventurous, Jack would have been a great match for Miranda — he also loves historical biographies! — if not for his “getting caught in the act” fetish. Fine in a taxi, not so much in front of his parents.

77. Don (John Dossett)

HBO

Paired with: Samantha
First appearance: Season 2, Episode 13, “Games People Play”
The verdict: A good lay, to be sure, but Don could only get it up when his team won. That’s a bit too limiting for Samantha.

76. Howie Halberstein (Bryan Callen)

HBO

Paired with: Carrie
First appearance: Season 6, Episode 8, “The Catch”
The verdict: Harry’s best man was such a nice Jewish boy, he felt like a good fit for Carrie. He ended up being terrible in bed (and a little painful, leaving Carrie with “a sex sprain” on Charlotte’s wedding day), but hey, at least he looked good in a tux.

75. James (James Goodwin)

HBO

Paired with: Samantha
First appearance: Season 1, Episode 12, “Oh Come All Ye Faithful”
The verdict: James was the perfect man for Samantha — she was finally in love! But his penis just wasn’t big enough for her. While many women can overlook that sort of thing, Samantha is just too phallocentric to let it slide.

74. Keith Travers (Vince Vaughn)

HBO

Paired with: Carrie
First appearance: Season 3, Episode 14, “Sex and Another City”
The verdict: He was a handsome publicist who swept Carrie off her feet, but it turned out Kevin wasn’t being all that honest about his living or professional situation. (He was actually Carrie Fisher’s personal assistant, who tried to pass off his boss’ place as his own.) Still, this was Vince Vaughn in his prime. And everyone lies a little in L.A.

73. Ethan Watson (Rob Campbell)

HBO

Paired with: Miranda
First appearance: Season 2, Episode 6, “The Cheating Curve”
The verdict: Ethan needed to watch porn in order to have sex with Miranda. It’s not that unusual: Lots of men and women use porn to get in the mood. But every time? That’s a deal breaker.

72. Harris Bragen (Clark Gregg)

HBO

Paired with: Miranda
First appearance: Season 3, Episode 12, “Don’t Ask, Don’t Tell”
The verdict: He wasn’t really a doctor. But then, Miranda wasn’t really a stewardess. Since they were both in the wrong, it’s kind of a draw.

71. Joe (Nick Scotti)

HBO

Paired with: Samantha
First appearance: Season 5, Episode 4, “Cover Girl”
The verdict: Not exactly marriage material, but Joe the Worldwide Express delivery guy was at least hot. And his brief fling with Samantha felt like something straight out of a fantasy — or cheesy porn.

70. Alexander Lindley (Christopher Orr)

HBO

Paired with: Charlotte
First appearance: Season 3, Episode 6, “Are We Sluts?”
The verdict: Look, calling someone a “whore” or a “slut” during sex is fine as long as it’s consensual. But, for all of his charm, Alexander couldn’t stop shouting these words at Charlotte. And he didn’t remember doing it, so…issues.

69. Ted (David Aaron Baker)

HBO

Paired with: Miranda
First appearance: Season 1, Episdoe 6, “Secret Sex”
The verdict: Really into spanking. Fine for some, but not everyone’s cup of tea. Certainly not Miranda’s.

68. Chip Kil-Kenney (Victor Webster)

HBO

Paired with: Samantha
First appearance: Season 6, Episode 1, “To Market, to Market”
The verdict: So hot. So going to prison for insider trading. But at least he gave Samantha some hot stock tips before he got taken away by the FBI. And that body!

67. Arthur (Brad Beyer)

HBO

Paired with: Charlotte
First appearance: Season 3, Episode 1, “Where There’s Smoke…”
The verdict: Arthur seemed like Mr. Right from the get-go — he was Charlotte’s knight in shining armor. But it soon became clear that he really just liked picking fights with people, which is a less attractive quality.

66. Caleb MacDougal (Ritchie Coster)

HBO

Paired with: Samantha
First appearance: Season 3, Episode 12, “Don’t Ask, Don’t Tell”
The verdict: Accents are hot, until you actually can’t understand what the other person is saying. Oh, well. Samantha didn’t need to be able to decipher Caleb’s speech to sleep with him.

65. Chivon Williams (Asio Highsmith)

HBO

Paired with: Samantha
First appearance: Season 3, Episode 5, “No Ifs, Ands, or Butts”
The verdict: Chivon and Samantha could have made it work — they definitely looked damn good together — if Chivon’s family hadn’t instantly disapproved of the union. Or if Chivon had been willing to stand up to his bossy sister Adeena (Sundra Oakley).

64. Wylie Ford (Brian Van Holt)

HBO

Paired with: Charlotte
First appearance: Season 2, Episode 10, “The Caste System”
The verdict: Charlotte got to be part of hunky actor Wylie’s entourage, which was thrilling for a while. The fact that he was looking for a fan more than a partner made this an ultimately unsatisfying match.

63. Bill Kelley (John Slattery)

HBO

Paired with: Carrie
First appearance: Season 3, Episode 1, “Where There’s Smoke…”
The verdict: The problem with handsome politician Bill wasn’t his pee fetish (well, OK, that might be a deal breaker for some); it’s the fact that he dumped Carrie because her column reflected poorly on his candidacy. Not cute.

62. Vaughn Wysel (Justin Theroux)

HBO

Paired with: Carrie
First appearance: Season 2, Episode 15, “Shortcomings”
The verdict: Ugh, this would have been so great — Vaughn was a writer like Carrie, and he came from this wonderful, artsy New York family (Valerie Harper played his mom!). But he couldn’t have sex (or even come close) without prematurely ejaculating. Sigh.

61. Martin Healy (Mike Dooly)

HBO

Paired with: Charlotte
First appearance: Season 2, Episode 7, “The Chicken Dance”
The verdict: Charlotte enjoyed a whirlwind romance with Martin at a friend’s wedding. The only problem was that his dad turned out to be a creep — and Martin took his side over Charlotte’s.

60. Ricky (Michael Lombardi)

HBO

Paired with: Samantha
First appearance: Season 3, Episode 1, “Where There’s Smoke…”
The verdict: Dumb, uncouth, but totally ripped, Ricky fit Samantha’s firefighter fantasy perfectly. But once he had to leave to fight an actual fire, the effect wore off.

59. Matt (Chris Tardio)

HBO

Paired with: Samantha
First appearance: Season 3, Episode 4, “Boy, Girl, Boy, Girl…”
The verdict: This smug asshole was Samantha’s assistant until she fired him. And then they had great sex. That being said, he’s still a smug asshole.

58. Dave (Daniel Travis)

HBO

Paired with: Miranda
First appearance: Season 4, Episode 2, “The Real Me”
The verdict: Miranda’s hot gym date Dave gave her a boost of confidence. And then he accused her of being too full of herself. You really can’t win with some of these guys, can you?

57. Ken (Jonathan Walker)

HBO

Paired with: Samantha
First appearance: Season 1, Episode 8, “Three’s a Crowd”
The verdict: Samantha had no moral qualms about sleeping with a married man, but when Ken insisted on bringing his wife into the equation, things got way too complicated. And icky.

56. Brad (Ted King)

HBO

Paired with: Samantha
First appearance: Season 4, Episode 7, “Time and Punishment”
The verdict: Taxi thief Brad wasn’t a very nice guy, but there was an intense fire in his brief fling with Samantha. Although he tackily asked her to shave her pubes, he was willing to do the same, so points there. Kind of.

55. Warren (John Bolger)

HBO

Paired with: Samantha
First appearance: Season 4, Episode 6, “Baby, Talk Is Cheap”
The verdict: Fantastic in bed — until he busted out the baby talk. There are some things you just can’t get past. And when Sam called him on it, he threw a toddler-sized tantrum.

54. Dr. Bradley Meego (Patrick Breen)

HBO

Paired with: Carrie
First appearance: Season 2, Episode 17, “Twenty-Something Girls vs. Thirty-Something Women”
The verdict: There was nothing wrong with Bradley, really — I mean, he was a doctor. But he didn’t exactly sweep Carrie off her feet, and once she ran into Big and Natasha, he was a total afterthought.

53. Josh (Mark Feuerstein)

HBO

Paired with: Miranda
First appearance: Season 2, Episode 4, “They Shoot Single People, Don’t They?”
The verdict: Totally cute and very sweet on Miranda. Unfortunately, Josh was incapable of giving her an orgasm, and didn’t seem to notice that Miranda was obviously faking it.

52. Nick the Wrestling Coach (Peter Onorati)

HBO

Paired with: Samantha
First appearance: Season 4, Episode 8, “My Motherboard, My Self”
The verdict: We never really got to know Nick, but what’s there to know besides the fact that he’s a wrestling coach who was able to help Samantha find her orgasm again? Kudos to him.

51. Spring Roll Guy/Aaron (Neil Pepe)

HBO

Paired with: Miranda
First appearance: Season 2, Episode 2, “The Awful Truth”
The verdict: Talking dirty is a great skill, and Spring Roll Guy definitely got Miranda to open up. But he totally flipped out when she mentioned that he enjoyed getting a finger in his butt. Relax, Spring Roll Guy.

50. Dr. Mark Raskin (Billy Wirth)

HBO

Paired with: Samantha
First appearance: Season 3, Episode 7, “Drama Queens”
The verdict: Dr. Raskin turned Samantha on to the power of Viagra when he shared his supply with her. But she ended up far too reliant on the wonder drug, and sex without it just wasn’t the same.

49. Marathon Man (Michael Knowles)

HBO

Paired with: Miranda
First appearance: Season 4, Episode 6, “Baby, Talk Is Cheap”
The verdict: A nice guy, and one who Miranda could run with. Marathon Man was just way too into analingus, particularly after running. And I’m sorry, but you have to really love someone to get into that.

48. Paul (Rob Bogue)

HBO

Paired with: Charlotte
First appearance: Season 2, Episode 1, “Take Me Out to the Ballgame”
The verdict: Charlotte couldn’t take Paul anywhere because he had the unpleasant habit of constantly adjusting his crotch. When she offered to buy him underwear that actually fit, Paul said they were moving too fast. OK, buddy.

47. Detective Stevens (Timothy Gibbs)

HBO

Paired with: Miranda
First appearance: Season 3, Episode 17, “What Goes Around Comes Around”
The verdict: Miranda’s lack of self-confidence made it hard for her to date the dreamy Detective Stevens. She finally downed a bottle of liquid courage, at which point he lightly accused her of being an alcoholic. A little judgmental, really.

46. Tom (Craig Gass)

HBO

Paired with: Miranda
First appearance: Season 5, Episode 4, “Cover Girl”
The verdict: Tom and Miranda met at a Weight Watchers meeting, which is completely valid. But they seemed to bring out the worst in each other’s eating issues, and Miranda had a problem with Tom’s other oral proclivities. He was just a messy eater.

45. Garth (James MacDonald)

HBO

Paired with: Samantha
First appearance: Season 3, Episode 13, “Escape from New York”
The verdict: Dildo model Garth was more than man enough for Samantha, and he turned out to be more than just well-hung; he also displayed an interest in poetry. Making anyone listen to your poems, however, is a total turn-off.

44. George (Josh Hamilton)

HBO

Paired with: Miranda
First appearance: Season 3, Episode 10, “All or Nothing”
The verdict: Such a cutie! Miranda’s fellow lawyer lived several cities away, but after a perfect date, they decided to continue their relationship via phone sex. And then she found out he was phone sexing other ladies.

43. Tom (Tom Gilroy)

HBO

Paired with: Charlotte
First appearance: Season 2, Episode 4, “They Shoot Single People, Don’t They?”
The verdict: The problem was, Charlotte never really wanted to date her out-of-work actor turned handyman. She liked him just enough to try dating him so he wouldn’t move to Salt Lake City, but it was bound to fail.

42. Patrick Casey (Richard Joseph Paul)

HBO

Paired with: Carrie
First appearance: Season 2, Episode 16, “Was It Good for You?”
The verdict: Carrie was totally smitten with Patrick, although he took a while to come around. He eventually revealed he was a recovering alcoholic and was trying not to date. He soon transferred that addiction unto Carrie. Bad news.

41. Wade (Cane Peterson)

HBO

Paired with: Carrie
First appearance: Season 3, Episode 15, “Hot Child in the City”
The verdict: Wade was a total man-child, down to his obsession with comics and his preferred form of transportation (the scooter). It was nice to see Carrie loosen up and smoke some weed on his roof, but the guy lived with his parents. No thanks.

40. Farmer Luke (Christopher Braden Jones)

HBO

Paired with: Samantha
First appearance: Season 4, Episode 9, “Sex and the Country”
The verdict: Farmer Luke was fine for a fuck — ideal, actually. But it could never work in the long run, seeing as he lives in the country, and Samantha is very much a city girl.

39. Wesley York (Jack Mulcahy)

HBO

Paired with: Samantha
First appearance: Season 2, Episode 15, “Shortcomings”
The verdict: Charlotte’s brother had a lot going for him, but he was also still smarting from a recent divorce. While Samantha could do a lot worse — and did — dating a good friend’s brother is inevitably too tricky to be worth it.

38. Jack (Joseph Murphy)

HBO

Paired with: Charlotte
First appearance: Season 1, Episode 8, “Three’s a Crowd”
The verdict: In many ways, Jack was ideal for Charlotte, but like all of her suitors, he had one major flaw; in this case, he was very pushy about having a threesome. Sorry, buddy. This is Charlotte York. Not gonna happen.

37. Eric (Terry Maratos)

HBO

Paired with: Charlotte
First appearance: Season 4, Episode 18, “I Heart NY”
The verdict: Eric had so much potential! Too bad he freaked out when he saw Charlotte’s opulent apartment — which, incidentally, was Trey’s!

36. Seth Robinson (Jon Bon Jovi)

HBO

Paired with: Carrie
First appearance: Season 2, Episode 13, “Games People Play”
The verdict: It’s never a good idea to pick someone up at therapy, but Seth was too cute to resist. The only real issue was that he admitted to Carrie, post-sex, that he always lost interest in women after sleeping with them. Awkward.

35. Sam (Timothy Olyphant)

HBO

Paired with: Carrie
First appearance: Season 1, Episode 4, “Valley of the Twenty-Something Guys”
The verdict: Great kisser and very cute. Carrie had a nice time with Sam until the morning after, when she realized he was very much a guy in his twenties. Hey, there are worse things.

34. Walker Lewis (Robert John Burke)

HBO

Paired with: Miranda
First appearance: Season 4, Episode 13, “The Good Fight”
The verdict: Walker was Miranda’s last fling before giving birth, and what a fling he was. Sadly, when he returned the following season, he wasn’t entirely comfortable with Miranda’s screaming infant. Fair.

33. John (Dean Winters)

HBO

Paired with: Carrie
First appearance: Season 2, Episode 14, “The Fuck Buddy”
The verdict: Carrie had such a good time in bed with her fuck buddy. It’s really too bad that didn’t translate into an actual relationship, because sexual chemistry is so important. But if we’re basing these rankings on dateability…

32. Brian (Josh Stamberg)

HBO

Paired with: Charlotte
First appearance: Season 1, Episode 4, “Valley of the Twenty-Something Guys”
The verdict: Charlotte freaked out when Brian asked for anal sex, which is reasonable. But here’s the thing: When she finally told him she couldn’t do it, he was totally willing to move on.

31. Michael Conway (Jack Koenig)

HBO

Paired with: Charlotte
First appearance: Season 1, Episode 7, “The Monogamists”
The verdict: Another one of Charlotte’s boyfriends with a sexual desire she couldn’t handle. In this case, however, that desire was oral sex, which is really very standard. Come on, Charlotte.

30. Gilles (Ed Fry)

HBO

Paired with: Carrie
First appearance: Season 1, Episode 5, “The Power of Female Sex”
The verdict: So charming, so French. Gilles left a bad taste in Carrie’s mouth when he gave her some money after sex. But OK, it’s not like it was directly after. Maybe he was just being generous! Not the best look, to be sure.

29. Aleksandr Petrovsky (Mikhail Baryshnikov)

HBO

Paired with: Carrie
First appearance: Season 6, Episode 12, “One”
The verdict: Honestly, what did Carrie ever see in this guy? Sure, he was rich and he spirited her away to Paris, but he never really got Carrie at all. Worth a fling, maybe, but not a serious relationship.

28. Adam Ball (Bobby Cannavale)

HBO

Paired with: Samantha
First appearance: Season 3, Episode 9, “Easy Come, Easy Go”
The verdict: Yeah, yeah, the guy with the “funky spunk.” But honestly, there are so many ways around that, and Adam was adorable. I mean, look at those eyebrows. Sorry, Sam, but this didn’t need to be a deal breaker.

27. Tom Reymi (Sam Robards)

HBO

Paired with: Samantha
First appearance: Season 3, Episode 11, “Running with Scissors”
The verdict: Samantha was all flustered when her sexual equal Tom Reymi asked her to get an AIDS test before sex. But that is a good thing. The fact that his sex swing broke during the act, less so.

26. Baird Johnson (Donovan Leitch)

HBO

Paired with: Charlotte
First appearance: Season 3, Episode 4, “Boy, Girl, Boy, Girl…”
The verdict: Baird was a handsome artist Charlotte seduced whose only flaw was letting Charlotte take the lead. She didn’t like what he brought out in her. Uh, all right.

25. Thor (Chris John)

HBO

Paired with: Samantha
First appearance: Season 2, Episode 6, “The Cheating Curve”
The verdict: Yes, he shaved a lightning bolt into Samantha’s pubes. But he’s also a sexy gym instructor named Thor. For sexy gym instructors named Thor, you let these things go.

24. Jake (Bradley Cooper)

HBO

Paired with: Carrie
First appearance: Season 2, Episode 4, “They Shoot Single People, Don’t They?”
The verdict: What do you really need to know about Jake? He was single, a smoker, and played by Bradley Cooper. Honestly, Carrie could have snagged him early on and spared herself a lot of heartache.

23. Trey MacDougal (Kyle MacLachlan)

HBO

Paired with: Charlotte
First appearance: Season 3, Episode 7, “Drama Queens”
The verdict: On paper, Trey was perfect. In the bedroom, not so much. But Charlotte’s fleeting husband did have his charms. And he probably would’ve been a lot more tolerable without Bunny, his awful mother.

22. Gardener (Steve Richard Harris)

HBO

Paired with: Charlotte
First appearance: Season 3, Episode 17, “What Goes Around Comes Around”
The verdict: That’s right, the gardener gets a higher ranking than Trey. Hey, the gardener was able to give Charlotte what she needed. Also, look at him.

21. Jeff Fenton (Anthony Alessandro)

HBO

Paired with: Samantha
First appearance: Season 3, Episode 2, “Politically Erect”
The verdict: Dapper but very, very short. That aside, Jeff proved himself to be incredible in bed — and he had a great sense of humor about his height. Why couldn’t Samantha let their size disparity go?

20. Richard Wright (James Remar)

HBO

Paired with: Samantha
First appearance: Season 4, Episode 10, “Belles of the Balls”
The verdict: At times, Richard was the perfect man for Samantha. And then he would go and do something that proved him to be the worst. Either way, their relationship brought out some of the best in both of them, for a time.

19. Mike (Alex Draper)

HBO

Paired with: Charlotte
First appearance: Season 2, Episode 9, “Old Dogs, New Dicks”
The verdict: Charlotte didn’t like the man Mike became after she talked him into getting an adult circumcision. But he was perfectly fine before that, damn it. If she’d left his penis alone, they’d probably be married.

18. Jeremy (David Duchovny)

HBO

Paired with: Carrie
First appearance: Season 6, Episode 10, “Boy, Interrupted”
The verdict: Carrie’s high school sweetheart Jeremy returned and took Carrie out on a wonderful date. Then he had to go and admit that he had committed himself to a mental hospital. Whatever. Still one of the saner guys on this list!

17. Mitch/Mr. Pussy (Charlie Schroeder)

HBO

Paired with: Charlotte
First appearance: Season 2, Episode 3, “The Freak Show”
The verdict: Honestly, Mr. Pussy is probably too high in these rankings. But for him to be that good at his one true passion in life is commendable. Not to mention the fact that Charlotte desperately needed to loosen up.

16. Ray King (Craig Bierko)

HBO

Paired with: Carrie
First appearance: Season 4, Episode 3, “Defining Moments”
The verdict: Sexy jazz musician Ray seduced Carrie into his frenetic musician world. A little too frenetic, yes — Carrie later diagnosed him with ADD — but he had serious potential, especially with a little medication.

15. Justin Anderson III (Peter Giles)

HBO

Paired with: Charlotte
First appearance: Season 5, Episode 5, “Plus One Is the Loneliest Number”
The verdict: You can tell Justin Anderson III would have been perfect for Charlotte, because, duh, look at his name. But then she neglected to mention that she was still married to Trey. It’s no wonder Justin bolted.

14. Sean (Eddie Cahill)

HBO

Paired with: Carrie
First appearance: Season 3, Episode 4, “Boy, Girl, Boy, Girl…”
The verdict: What was the problem with Sean exactly? He was completely adorable (hello, it’s Tag from Friends) and sweet. The fact that Carrie was turned off by his bisexuality just shows how ’90s this series was at times.

13. Simon Cobb (Daniel McDonald)

HBO

Paired with: Miranda
First appearance: Season 2, Episode 15, “Shortcomings”
The verdict: The only problem with Simon was his timing. Miranda couldn’t deal with this hunky and kindhearted DILF because she was child-phobic and he had a kid. Give it a few years, Miranda!

12. Stephan (Dan Futterman)

HBO

Paired with: Charlotte
First appearance: Season 2, Episode 11, “Evolution”
The verdict: What woman hasn’t wanted to date a gay man? And Stephan isn’t even gay — he’s just a stereotypically gay-acting man who is sexually attracted to women. Charlotte should never have let this catch go.

11. Skipper Johnston (Ben Weber)

HBO

Paired with: Miranda
First appearance: Season 1, Episode 1, “Sex and the City”
The verdict: Skipper was such a dweeb, but he was Miranda’s dweeb. (Honestly, he’s not that different than Steve.) Plus, he was a genuinely sweet (if not a little mopey) guy and cuter than any of the women gave him credit for.

10. Jack Berger (Ron Livingston)

HBO

Paired with: Carrie
First appearance: Season 5, Episode 5, “Plus One Is the Loneliest Number”
The verdict: Berger could have been the one for Carrie. He was handsome. He was a writer. But he was also overly competitive. And in the end, he broke up with her via Post-It. Sigh. Those eyebrows, though.

9. Sean (Scott Rabinowitz)

HBO

Paired with: Carrie
First appearance: Season 1, Episode 3, “Bay of Married Pigs”
The verdict: There was nothing wrong with Sean. Nothing! It’s just that he was the marrying type, and Carrie was nowhere near the point in her life at which she wanted to be married. Which is not Sean’s fault, mind you.

8. Ben (Ian Kahn)

HBO

Paired with: Carrie
First appearance: Season 2, Episode 3, “The Freak Show”
The verdict: Ugh, Carrie. Another good guy she totally ruined things with. Ben was cute and funny, but of course, Carrie insisted on finding something wrong with him, so she snooped through all of his things. He was right to dump her.

7. The New Yankee/Joe (Mark Devine)

HBO

Paired with: Carrie
First appearance: Season 2, Episode 1, “Take Me Out to the Ballgame”
The verdict: If you’re going to rebound, rebound with a hot baseball player. This was just an issue of timing. Sure, Carrie may not have liked the tabloid attention, but she was too hung up on Big to give things with Joe a real shot.

6. Dr. Robert Leeds (Blair Underwood)

HBO

Paired with: Miranda
First appearance: Season 6, Episode 9, “A Woman’s Right to Shoes”
The verdict: That hot and a doctor? If Miranda hadn’t been simultaneously crushing on her baby daddy Steve, she and Dr. Robert could have made beautiful babies together. And watched shitty British soaps.

5. Mr. Big (Christopher Noth)

HBO

Paired with: Carrie
First appearance: Season 1, Episode 1, “Sex and the City”
The verdict: Carrie’s on-again off-again relationship with Mr. Big dominated much of the series. In the end, he turned out to be a rather decent guy. But man, the crap he put her through in the process. If he weren’t so handsome…

4. Aidan Shaw (John Corbett)

HBO

Paired with: Carrie
First appearance: Season 3, Episode 5, “No Ifs, Ands, or Butts”
The verdict: Yep, Aidan was a better match than Big. The truth hurts, don’t it? He forgave Carrie for cheating on him and came back looking more attractive than ever. It’s too bad these two could never seem to make it work.

3. Steve Brady (David Eigenberg)

HBO

Paired with: Miranda
First appearance: Season 2, Episode 8, “The Man, The Myth, The Viagra”
The verdict: Aw, Steve! He was always so kind and patient with Miranda. And yes, he had his own issues, but he matured beautifully throughout the series. Who knew a one-night stand with a bartender could blossom into something so great?

2. Harry Goldenblatt (Evan Handler)

HBO

Paired with: Charlotte
First appearance: Season 5, Episode 7, “The Big Journey”
The verdict: Sweaty, awkward, and rough around the edges, Harry wasn’t what Charlotte was looking for in a husband. But he turned out to be a better man than she could have hoped for, finally giving her the life she’d always dreamed of.

1. Smith Jerrod (Jason Lewis)

HBO

Paired with: Samantha
First appearance: Season 6, Episode 2, “Great Sexpectations”
The verdict: Does anyone as beautiful and innately good as Smith actually exist in real life? Probably not. But he became so much more than man candy for Samantha, staying by her side as she struggled with chemo. All in all, the perfect man.

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