Sex and the City aired its first episode on June 6, 1998. In honor of the occasion, we’re taking a look back at 20 years of SATC. Read all the Cut’s anniversary coverage here.
In its six seasons and 94 episodes, between its four main characters and their on-again-off-again steady romances, Sex and the City presented us with a lot of flings. Many were very terrible, others were somewhat fine, a few were good, and one was great. Let us remember all of them, painful as it may be, from worst to best, together.
We’ll begin with Ed.
This 72-year-old millionaire was friends with Donald Trump, plus he had a saggy butt. He’s the worst.
93. Harvey Terkell
This guy basically had a slave.
92. Martin Healy
This guy was doing pretty well with Charlotte — they met at a wedding, remember? The one where Carrie had to read a poem and then they had sex on the rose petals — until his dad grabbed her ass and he didn’t believe her when she told him about it. Damn. Believe women, Martin. Your dad’s a creep. And so are you!
Why did Samantha date Don? There is a lot of truth to be found in Sex and the City, but also there were a lot of scenes where they’d walk into a room full of ugly dudes and Samantha would say something like, “Look at all these sexy, available men!” In my youth I thought maybe I’d “get it” as an adult and suddenly these horrible-looking dudes would become attractive to me, but I’m an adult now and a lot of these dudes are just not cute at all, including Don, who would only sleep with Samantha when the Knicks won.
Oh my God, remember Barkley? You might have somewhat fond memories of Barkley because he was cute and an artist — “he’s probably at least not as bad as Dominic, who I see is next,” you might be thinking — but do you remember that he taped the models he had sex with while they were having sex … without their permission?! For “art”?!?! Barkley should be in jail! Jesus. Carrie, why were you friends with Barkley? (He had sex with Samantha.)
This jerk. He broke Samantha’s heart. Then she thought she could break his heart to get back at him, but then he broke her heart again before she could do it! What a dick. I recently saw him in a bit part on a short-lived ABC drama about a magician cop, though, so I guess he got his.
Ugh, I hated this guy. The mean attorney who dated Miranda, remember? Why did she put up with that shit? Because the sex was good? Miranda, please don’t date a guy who yells at the waitstaff just because you like having sex with him. He’s rude!
Oh God, Jack. He could only have sex when there was a chance he could get caught. He made Miranda have sex with him in front of his parents!
Ugh, Arthur! Arthur made Charlotte feel like he was a protective gentleman when that one guy was hitting on her, but really he just liked punching people and causing a big scene. No thanks!
85. Alexander Lindley
Oh God, speaking of Charlotte, remember this guy? He would shout “FUCKING WHORE!” and “FUCKING SLUT!” at Charlotte when they were having sex, and then when she told him she didn’t like it he’d say he didn’t remember doing it! No thanks!
This guy went to the bathroom with the door open. No thanks!
This guy liked going down on Charlotte — too much. He was very gross about it once at dinner. Remember? He shoved his face into some sort of fruit?
Charlotte met this young guy at the beach and then he gave her crabs!
This guy dated Carrie first and then Miranda. Carrie warned Miranda that he was a jerk, but she decided to give him the benefit of the doubt. Their relationship ended at a dinner with Carrie, for a reason I forget (why would Carrie come? I don’t know), where Jim screamed at Carrie for being an asshole, and then screamed at Miranda for defending Carrie. “OOooh, the fancy lawyer lady is breaking up with me, like I give a shit!” he yelled. Man. Terrible guy.
Jack was very pushy and manipulative with Charlotte about having a threesome, and when she finally caved all he wanted to do was have sex with the other woman. Just have sex with another woman, then, Jack! What is wrong with you! Plus, you look evil!
79. Wiley Ford
Wylie Ford was a famous “Brad Pitt” type of man, I guess. Maybe younger than Brad Pitt. In any case, he was famous and he thought the fire extinguisher at Charlotte’s gallery was art, and he was very rude to Charlotte around his hanger-on friends. Not a good or smart guy. But I do commend Charlotte for at least attempting to have sex with a celebrity, good for her.
78. Ethan Watson
Ethan dated Miranda and would only have sex with her while watching porn. When Miranda asked if maybe they could have sex without watching porn, Ethan said, “I’ve only known you for a few weeks, but I’ve been involved with some of those women for years!” All right, Ethan. K. Enjoy them.
77. Dick Cranwell
This guy was a rich philanthropist who Samantha was trying to get to donate money to some cause. Remember? I bet you don’t remember, but that’s okay — it was very minor. She ended up almost sleeping with him before his wife walked in and caught them in the act, then the wife attempted to ruin Samantha’s philanthropic reputation. Men who are publicly charitable and privately demons? The worst!
Remember William? He was the club owner (the club where all the girls went dancing when they all found themselves single together, remember, the night before Carrie’s New York photo shoot when she stayed out too late?) who promised Samantha fancy dinners and vacations and then stood her up on their first date. What a jerk!
75. Wade Adams
Oh God, WADE! Wade the comic-book guy. Yuck. I always disliked Wade. This guy lived with his mom, who caught him and Carrie smoking weed one day. Then he said it was Carrie’s weed! It wasn’t! Grow up, Wade. Move out of your mom’s house, dude. You’re an adult. You suck.
Ned’s wife died and Charlotte thought she was dutifully comforting him about it, until she learned several other women were also dutifully comforting him about it. Damn. Everyone grieves in their own way, but show some respect for your wife, Ned. At least show some respect for Charlotte. She’s rich!
73. Kurt Harrington
Kurt’s the guy from the pilot who Carrie says is a “self-centered, withholding creep.” We didn’t really see too much from him, so we have to take her word on it. He certainly didn’t seem nice!
72. Dave From Crunch
Miranda met Dave at the gym and he found her sexy until she gained confidence. Remember? All right. Real nice, Dave.
71. Patrick Casey
This guy was the recovering alcoholic who screamed outside of Carrie’s window. We all have our demons.
70. Thomas John Anderson
This guy was an up-and-coming (haha) playwright who had to shower after he had sex with Miranda due to his Catholic guilt. Do you think he’s supposed to be Paul Thomas Anderson? Damn, I never thought about that until right now. I guess I never really considered his full name until I had to write it into this list. Huh. Anyway, after Miranda confronted him about it, he doubled down on the inherent Catholic dirtiness of sex. He didn’t kill anybody or anything, and he at least wasn’t Big, but still not great.
69. Len Schneider
Yuck, ew, I really did not like this dude. Samantha dated him when she thought she was going through menopause and had to find someone to settle with before all of her options dried up, but then she got her period all over his sheets — thank God!
68. Howie Halberstein
Carrie slept with Howie the night before Charlotte’s wedding. He was terrible at sex, fucked up her back, and then went insane because she didn’t want to date him again. And then he gave a bonkers toast about it at the wedding reception! Howie, my man, you need to chill out.
67. Keith Travers
Keith lied about everything, but Carrie did get to party in a VIP room, see an expensive Los Angeles loft, and meet Carrie Fisher. So not too bad, really.
66. Ted Baker
Ted liked spanking and Miranda didn’t, which was an issue, but then he didn’t like it when she brought it up in a lighthearted way after she got over the fact that she didn’t like it. I guess because she was making fun of him. Huh. In that case he’s not so bad, actually.
65. Dr. Bram Walker
Ugh, BRAM! Bram wasn’t that bad — he was the surgeon who fell asleep during sex with Charlotte, remember? She was very offended by it, but it sounded like he had a pretty busy day. So. Not so bad, in my opinion. But it’s fun to say (type), “Ugh, BRAM!!!!!!”
This was a young guy who Samantha had sex with. He’s incredibly inconsequential as you could maybe tell by his name — “Jon” — except for how he told Samantha that she had “cute neck wrinkles,” which caused her to realize that if she dated a younger man she’d always be the older woman. She forgot that she cared about this, as we know, but it was true for her for a moment. Jon … come on, man.
Ahh, Brad. The bad kisser guy, remember him? Charlotte couldn’t get over his sloppy, disgusting kisses, and honestly I don’t blame her. Get a clue, Brad.
62. Luke the Manhattan Guy
God, this guy sucked. He was extremely vocal about never leaving the city. All right, man. You can have it.
Oh wait, this guy also told Samantha she was old! He was a lawyer and said something to her about how sexual harassment cases were often brought against the older woman, insinuating that she was an older woman. How dare he. And then he got all done up in his BDSM closet. I imagine Samantha would have been into it if he hadn’t called her old. Samantha is very open sexually but very sensitive about her age, HARRISON!
60. Vaughn Wysel
Justin Theroux played two characters on Sex and the City, but only one managed to go home with Carrie. (The other was left at a party and only used to make Big jealous over the phone. It was at a New York Magazine party!) Carrie dated the other Justin Theroux, though — this guy, Vaughn Wysel. She liked him because he was a novelist with a cool New York City family, but unfortunately he was also a premature ejaculator. Damn.
Oh, it’s another Brad. This Brad stole Samantha’s cab and then asked her to shave her pubic hair. Extremely rude. She was offended by both acts, but she got in the cab with him and, later, made him shave his own pubic hair, so. She seemed fine after that.
This is just a delivery guy Samantha gave a blowjob to, before Carrie walked in and interrupted. We learn nothing about him other than that he’d accept a blowjob from Samantha, but he has to be somewhere on the list, so here he is at number 59. Hello, Joe.
Josh couldn’t give Miranda an orgasm (even after she tried very patiently to teach him how) and he couldn’t tell when she was faking it. “Oh, do you have, like, a physical problem or something?” he asked her. Uh. No, she doesn’t, Josh. And she went to Harvard Law! Show some respect!
Ugh, baby talk guy. “Titty witties.” No.
Sam was a young, cute guy, but his apartment was disgusting and he made coffee using toilet paper as a coffee filter. Remember that? What the fuck, man. I hate thinking about that and I think about it frequently.
54. Marathon Guy
“The cutest of the slow guys,” you may remember, from when Miranda was training to run the New York Marathon. He was too into analingus directly after running for Miranda’s taste, but, I don’t know, I guess it was nice that she had a running friend for a little while.
This fuckin’ guy. He was constantly adjusting his balls in public so Charlotte was like, Jesus Christ, I’m just going to buy this guy some underwear that fits his stupid balls. So she got him the nicest underwear that Barney’s sells and he said, “We haven’t even made love yet and you’re already out shopping for me? Slow down!” Uh, Paul? YOU’RE GROSS!
George was a cute lawyer from out of town. Miranda went on one date with him, hit it off, and continued the relationship via phone sex until she realized he was a non-monogamous phone sexer. Damn. Why didn’t he schedule his phone sexes at different times? It’s unclear.
This guy sucked, he’s only up this high on the list because he doesn’t matter and I sort of forgot about him. Sorry, MATT! He was Samantha’s assistant who would yell at people on the phone, even after she told him not to. Calm down, dude. Then they had sex!
50. The Turtle
Oh, the Turtle. Samantha thought she could turn this New York legend (a legend for his investment skills and his bad breath) around by dressing him up in Helmut Lang, and she did. He looked better, and people respected him more, and it was fine, but then he was still just so boring. Talking about mushrooms, etc. Who cares, Turtle.
Sean desperately wanted to get married during a period of time when Carrie thought she wasn’t the marrying kind. Probably most people are sensitive to Sean because he knew what he wanted, and it wasn’t his fault Carrie wasn’t in the same headspace or heartspace. I, however, am not sensitive to Sean in this way. He had one date with her and he was already parading her around like his fiancée? Give me a break, Sean. Relax!
48. Harris Bragen
Harris Bragen lied to Miranda and said he was a doctor while Miranda was lying to him, saying she was a flight attendant. Deeply embarrassing for everyone, but particularly for Harris because Miranda’s real job is high-powered lawyer and his real job is I don’t even remember.
Aaron liked talking dirty, which Miranda wasn’t into at first. Then she came around to the idea and said something about how he liked to have his butt fingered. He did not like that. Aaron, Miranda was just trying to do what you wanted. Chill out about your stupid butt!
46. Ken Shear
Ken Shear, a wine importer, was cheating on his wife with Samantha until his wife bumped into her while they were all buying flowers. Quelle horreur! Then, after telling his wife about his infidelity, Ken asked Samantha to join them in a threesome. Quelle horreur! Samantha, though she does enjoy playing the extra in a threesome, had to decline, and I have to tell Ken that he is gross, and I have to tell Ken’s wife that she deserves better than stupid old Ken.
45. Michael Conway
Charlotte thought she might marry Michael Conway because he was rich, but then he wanted her to give him blow jobs. She did not want to give him blow jobs, even though in another episode she said she liked to lick Trey’s butthole. It’s fine. Would she lick his balls at least, he asked? She would not. So they had to part. A fine decision for both of them.
44. Up the Butt Brian
Brian was Charlotte’s boyfriend for the infamous “up the butt girl” episode. (You learned about it in school, I assume?) Brian wanted Charlotte to do anal, and Charlotte, after much hemming and hawing and discussion with the girls, finally decided that it was not for her. Brian seemed fine with that and asked if they could have sex “the normal way,” but then he disappeared. He is at this point in the list, No. 44, because I do not know if he broke up with Charlotte or if Charlotte broke up with him. Maybe, fingers crossed, it will be discussed in the third movie if the third movie, fingers crossed, is ever filmed.
Jake was just some fine enough guy smoking in a bar, ready to hook up with Carrie, until he got some more cigarettes at a newsstand when Carrie’s New York cover was out. He brought the magazine to her and yelled “IS THIS YOU?!” Jake … yes, it was.
Eric freaked out because Charlotte had a nice apartment. Relax, Eric.
41. Sam Jones
Sam Jones was, essentially, a child that Samantha had sex with. After some sort of a telephone mix-up due to their similar names (it was something about how he was throwing a party and she kept getting calls about the party) she confronted him and took his virginity. Then he fell in love with her. Aw, Sam Jones.
He couldn’t have sex with Charlotte because he was on Prozac. He’s one of those guys where it’s like, I don’t know, I guess he was fine. No. 40.
This guy also couldn’t have sex, but for Siddhartha it was because he was practicing tantric celibacy. Samantha really wanted to do him, though. Damn.
38. Ray King
I really did not like Ray King, the jazz guy. I guess I liked when he slipped Carrie a note asking if Big was her boyfriend, but it was all downhill from there. The jazz, the scatting, his fuckin’ hat … spare me. This is the only scatting I want from a Sex and the City cast member. (I realize this overtly negative opinion of Ray King the jazz man may not be an opinion shared among those considering the Sex and the City flings but if you’d like to voice your opinion you’ll have to make your own list of all of them and I assure you making the list will be quite a process.)
Hey, look who it is! It’s Seth! Carrie met Seth at therapy; he was there because he always loses interest in women after sleeping with them. Carrie was there because she always picks the wrong guys. Incredible matchmaking. Thank you to Bon Jovi.
36. Walker Lewis
This guy broke up with Miranda because she had a crying baby (Brady). Crying babies are difficult, I will admit. And once Miranda broke up with a guy because he had a kid. (We haven’t gotten to him yet in this list.) So. Life is messy, I guess.
Lance went on a date with Miranda while she had adult braces. Man. She got so much food stuck in those braces, it was crazy. He wasn’t too mean about the braces during dinner, but he did joke, “So I guess a blow job is out of the question, then?” He didn’t seem too upset by the braces to me, but after the dinner Miranda thought she could never date again, because of the braces. It’s okay, Miranda.
He was Samantha’s trainer and he shaved a lightning bolt into her pubic hair. Turns out he was doing that to all the ladies, though. I think with him it’s basically, like … you know, all’s well that ends well.
33. Tom (a.k.a. Big Boned)
Miranda stopped having to see the nice man she met at Weight Watchers because he was a, uh, messy eater. It’s fine.
32. Dr. Mark Raskin
This guy wasn’t so bad, but he did briefly get Samantha mildly addicted to Viagra.
Oh my God, remember when Charlotte made this guy get an adult circumcision??!?!?!?!?!?!?! Jesus.
Ah, here he is — Carrie’s fuck buddy from 30 Rock and those commercials. Carrie used him reliably for sex, but could there possibly be something more there? Well, there could not, and it seems she had good reasons. He didn’t like sushi, and he said, to a sushi chef, “sake to me.” Better luck next time, with Liz Lemon.
Was he a gay straight man or a straight gay man? That was the question on everyone’s lips, when it was the episode with Stephan in it. Turns out he was, I guess, a “gay straight man.” Even though he was a pastry chef and knew what a dress was, Stephan wanted to have sex with Charlotte. Men! Unfortunately he was very freaked out by a mouse and Charlotte couldn’t handle it. I think that’s fair enough. It’s just a mouse, man.
28. Tom Reymi
This guy was good mostly just because he made Samantha get an AIDS test.
27. Justin Anderson III
This guy dated Charlotte while she was technically still with Trey, unfortunately, and their lovemaking was interrupted by Bunny (Trey’s mom, as you know). That’s why he’s so high on the list even though you don’t remember him. I don’t really remember him either, but it seems like he didn’t do anything wrong.
26. Simon Cobb
Speaking of guys who we kind of just have to get through, Miranda didn’t like this one because his kid was annoying. Otherwise he was fine. Check out this IMDB synopsis about it:
“Miranda considered Sunday a nightmare because children swarm everywhere, there is even a family hour at her gym, but it did allow her to meet hunky Simon Cobb, indulgent divorced father of rascal Simon, who loves to push the elevator’s buttons, and his; when Simon surprises her naked in the lo after a hot night, that signs her marching-orders.”
He would, like, fix things in Charlotte’s house? But then he moved to Salt Lake City? Who cares.
23. Caleb MacDougal
Caleb was the Scottish Groomsman at Charlotte’s wedding to Trey. Remember him? You couldn’t understand anything he was saying? He had sex with Samantha? He was cute enough, and he didn’t do anything egregiously bad. So. Nice going to Caleb.
24. Ricky the Firefighter
Oh, Ricky. There wasn’t really anything wrong with Ricky except for the fact that he was a firefighter who had to put out a fire at the exact moment Samantha was naked in his firehouse, which interrupted her fantasy. At least she got to slide down the pole.
22. Wesley York
Wesley York, as you may be able to tell by his last name, was Charlotte’s brother. He was divorced and he slept with Samantha in Charlotte’s apartment and Charlotte got mad and then we never heard about him again. I guess we rarely heard about any of their families unless somebody died, and we didn’t hear that Wesley died. So he must still be alive! Good for Wesley.
21. Jeff Fenton
This guy was great, or at least fine, I don’t know, I never met him personally, but he was too short for Samantha. Life is a cruel game of chance; I’m sure Jeff Fenton knows this more than most.
20. Mr. Cocky
Speaking of how life is a cruel game of chance, this guy’s penis was too big. Remember? I’ve always felt bad for him. It was very difficult for him to find a suitable lover, which is sad. It’s not his fault his penis was so big, too big even for Samantha. He was polite and charming and handsome. I’m sorry, Mr. Cocky.
19. Chip Kil-Kenney
This guy Chip, Samantha’s stockbroker neighbor, gave Samantha secret stock info her because her blow jobs were so good. And then he got arrested for insider trading! Damn. The stock tips were a pretty good perk, though, for Samantha, and he was already so hot.
Oh, poor James. Newton’s 69th law states that for every Mr. Cocky, there is a James. Samantha loved him — even said “I love you” to him! — but, unfortunately, his penis was too small for her. I’m sorry, James. At least you’re not Mr. Cocky; please count your blessings.
Aw, Garth was nice. He was a dildo model, perfect for Samantha, but also he was a poet, something Samantha could not take, even from a dildo model. I understand. It’s very difficult to deal with a man who wants to read something to you out loud, particularly if he is the one who wrote the something. He was nice, though. Sorry, Garth.
16. Detective Stevens
God, this guy was so handsome. (“How handsome was he?”) He was so handsome that Miranda had to get completely wasted to ease her mind about how insecure she felt about being seen with him, and then she was so fucked up that he thought she was an alcoholic and left her a number of a place where she could get help. Damn. Fuck. He was really handsome, though.
15. Bill Kelley
Ah, Bill Kelley! He was so charming and handsome. Yes he asked Carrie to pee on him, but he only wanted her to do it in the shower, and wasn’t she a sex columnist anyway? Dang. And yes, he dumped her because dating a sex columnist would be bad for his campaign, but politicians want for nothing but power, are uniformly evil, and are all liars. That’s not Bill Kelley’s fault!
14. Nick the Wrestling Coach
He helped Samantha get her orgasm back, and we all can’t thank him enough.
13. Dr. Bradley Meego
God, Dr. Bradley Meego was so boring even though he was rich and normal. He would have been the boringest boyfriend; I’m glad Carrie only semi-dated him for one or two episodes, or however long they were in the Hamptons. He was rich and normal, though, like I said, and Carrie only didn’t date him because she was hung up on Big, who is a terror. So. Still an eligible bachelor, I think.
12. Baird Johnson
Remember Baird? He was the photographer who took photos of men dressed as women and women dressed as men. An embarrassing idea of groundbreaking art, but he did at least succeed in getting Charlotte to toy with the strictly feminine idea she held of herself, dressing her up as a man for a photo shoot during which she — infused with masculinity and a sock in her pants and a mustache — came onto him. This is ultimately why she decided not to see him again. Charlotte is gonna be Charlotte, and that’s not Baird’s fault, even though his art is an America’s Next Top Model challenge.
11. Luke the Farmer
Samantha was bored in the country and just, like, found this guy to have sex with? Pretty good.
This guy was extremely decent, but he was bisexual, which Carrie infamously said was “just this layover on the way to gay town.” Yikes! Carrie! You’re a sex columnist! The bisexuality episode is one of the most cringeworthy episodes of Sex and the City, but it is at least not as cringeworthy as the episode we will discuss in No. 9, which is the next number.
9. Chivon Williams
Oh, God. This episode. I’m embarrassed to have to acknowledge it in this list. Samantha … the gold outfit … “big black ass” … oh my God … “all that” … I truly don’t even want to talk about it. I want to crawl into the floor. Maybe this show was bad? Anyway. Chivon was good.
Shmuel was a Hassidic folk artist with whom Charlotte had a brief but passionate fling. Remember Shmuel? They talked about art, and sex, and life, and love. She seemed to enjoy it.
Ben was in the “Freak Show” episode, if you remember. He was a journalist; Carrie met him in Central Park and they went on a “non-date” dinner, which turned into a non-non-date. He was hot and charming and Carrie ruined her chances with him when he caught her rifling through his belongings, looking for something that would prove him to be a freak. Oh no! It turns out Carrie is the freak. However, she did find a box of, like, old Cub Scout badges, which, if you ask me, in a grown man’s apartment, is fairly freaky. That is non-normal. Get rid of them … ? Ben’s still hot, however.
6. Adam Ball
I feel like you could get over the funky spunk.
5. Burt the Gardener
Thank God Charlotte hooked up with Burt the Gardener while she was married to Trey, who wasn’t having sex with her. He was so hot, and he cultivated life. She should have married Burt the Gardener!
4. Joe the New Yankee
Joe the New Yankee was so great, but, like pretty much everyone God damn else, Carrie ended it because she was hung up on Big. Fucking Carrie. What is wrong with you. Though I guess he could have been traded at some point, which would have been sad. But then it could have been like Sex in the City (St. Louis).
Okay, yes, fine, Jeremy was in a mental institution, but at least he knew he needed help! Big should have been in a mental institution! He was so sweet, and he looked exactly like David Duchovny. I love you, Jeremy.
Perhaps you don’t agree that the rich Frenchman who left Carrie $1,000 on the bedside table after sleeping with her, and let her use his credit card to order room service at the fancy hotel in which they had sex while he flew home to Paris or wherever is the second-best fling. Yes, Carrie was deeply offended at the envelope full of cash — they spent a very romantic afternoon together walking around Central Park, and she thought it was a date, she didn’t think she was a sex worker. But she got $1,000 and she got to invite all of her friends to the hotel room to have an enormous brunch, paid for whoever this guy was. That rules, in my opinion. She had sex with many terrible dudes, but this time she got over a month’s rent! (Her rent-controlled apartment was $750 a month.) Pretty good deal, I think.
1. Tommy the Doorman
Tommy. Here he is: our No. 1, our shining light. Charlotte’s Irish doorman from episode three. God, he was so hot. And so sweet! “Don’t be scared, miss. It’s me, Tommy. I’m leaving. Your friend invited me up. I know it was wrong, but I’ve just been so lonely since I left home…” Tommy, Tommy, Tommy. Samantha is the one who had sex with Tommy, but I fully believe that, at the end of everything, Carrie should have ended up with Tommy instead of Big. Maybe if there is a third movie Tommy can come back and marry Carrie. “Don’t be scared, miss. It’s me, Tommy. From episode three.”