If Carrie Bradshaw and her friends have taught us anything, it's that sometimes you have to kiss—and sleep with—a lot of frogs to find a prince.
On the cultural phenomenon known as Sex and the City, each of the women finds themselves questioning whether or not they should throw in the love towel. Is all that demoralization worth it? But in their own time, each learn the answer—abso-f***ing-lutely. So who are the real Prince Charmings? And who's just a handsome troll under the Brooklyn Bridge? Here are the five best and five worst relationships on Sex and the City, ranked.
(FYI, this writer refuses to embrace those abominable movies as canon. This list is based on the show, and the show alone).
10 Worst - Charlotte & Trey
Carrie warns us of the dangers of "on paper" guys. They're the sort who tick every box on our list of romantic criteria, who are absolutely perfect...on paper. Trey is Charlotte's "on paper" guy. He's a handsome doctor who comes from good WASP stock. Charlotte couldn't have dreamt up a better bachelor for her wish box if she tried.
But ever since that cringeworthy "alrighty!", Trey proves he's too good to be true. Living with impotence must carry a world of stress, but Charlotte has a right to know. Then there's his mother from hell, the unfittingly named Bunny, a total emotional carnivore. But Trey changing his mind about wanting kids is the last straw for Charlotte. She wants an active sex life and a happy home full of kids. Trey can't provide any of that. Ironically, it's after they decide to split that Trey delivers most. He poses with Charlotte for a photo spread in Home & Garden. They're the spitting image of the fantasy life Charlotte dreamed for herself. Sadly, it never became a reality with Trey.
9 Best - Carrie & Mr. Big
Speaking of fantasy lives...Critics of the show, and even some fans, have long since suggested that Sex and the City is actually science fiction. How does Carrie afford such a luxurious lifestyle and a gorgeous Upper East Side apartment by writing one newspaper column a week? This must be an alternate reality version of Manhattan.
Similarly, this logic would explain how Mr. Big, aka. the world's biggest commitment-phobe, chooses to settle down with Carrie. If this was real life, Carrie should have told Big to take a hike about eight heartbreaks ago. But in fantasy Carrie Bradshaw-land, the end of the series sees Big pouring his heart out, finally able to be the man Carrie wants. Flying to Paris is hardly the grandest gesture in the world—who doesn't want to go to Paris?—but the love is clearly there. They get each other in a way that most couples can only hope for. And that's just fabulous.
8 Worst - Carrie & Berger
This may be a hot take: Out of all of Carrie's boyfriends, she has the most chemistry with Berger. The most initial chemistry. Their witty writer's banter has the sprightliness of freshly popped champagne. Instead of all the drama and second-guessing, it looks like Carrie maybe found someone where things are just effortless.
Then the switch flips. Carrie gets a book deal and she's riding a career high. When she deigns to buy him a Prada shirt with her advance, you'd think Berger would be bowled over with appreciation. Nope. He views his girlfriend's success as a personal affront to his masculinity. In order to rewrite this wrong, he takes Carrie on a Mad Max-esque motorcycle ride that has her fearing for life. Despite these red flags, Carrie still tries to make things work until eventually, Post It Gate happens. What kind of guy breaks up with someone on a Post-It? A nothing Berger.
7 Best - Miranda & Robert
Robert has a terrible reputation for his actions post-Miranda breakup. Fair enough. He behaved like a horny infant. But from his perspective, Miranda really did him wrong. He clearly loved her and things were as close to perfect as possible—though maybe the "I love you" cookie was a misstep. Then out of the blue, Miranda dumps him for her the less successful, more dramatic ex, Steve. When Samantha plastered Richard's neighborhood with unflattering fliers, did we judge her?
Plus, when things were good with Miranda and Robert they were really good, and by that we mean really, really steamy. Robert has a self-assuredness missing from Miranda's past neurotic, man-child boyfriends. He's able to get her to loosen up without pressuring her. Not just anyone can get the workaholic Miranda to take a personal day. It just comes down to the "on paper" thing. On paper, Robert's a much better fit for Miranda than Steve. But paper isn't life.
6 Worst - Samantha & Richard
Richard is the grotesque, funhouse version of Samantha. Both of them are empowered go-getters who take no prisoners in the office or the bedroom. The only difference? Samantha's a straight shooter who has no qualms about telling her lovers they're welcome in her bed for one night, and one night only.
Then there's Richard. Every promise he makes practically oozes snake oil. With his phony-baloney lip service, he's able to achieve the impossible and get Samantha to open her heart—only to stomp all over it with his designer shoes. What's so infuriating is that if Richard came clean and said he wants to keep things casual and sleep with other women, Samantha would likely be game. But Richard turns out to be the poorest sport of all.
5 Best - Miranda & Steve
Miranda and Steve shouldn't work. She's a type-A cynic and he's a go with the flow romantic. But it would be inaccurate to write their love off under the cliché that opposites attract. If that's all it was, they would have had a dynamite one night stand, shook hands and parted ways. But Miranda and Steve really see each other; not just the constructed veneers they present to the world, but who they are underneath. And it's those people who fall in love.
Steve teaches Miranda that it's okay to slow down and let things just happen. She's successful and driven, but Miranda doesn't really stop to be happy. With Steve, she allows herself to be. She in turn teaches him that you can't always be passive in life and sometimes have to make things happen for yourself. As a result, he opens his own bar and it thrives. Even when apart, Miranda and Steve turn to each other in times of need. That speaks volumes much louder than anything written on a cookie.
4 Worst - Carrie & Petrovsky
Carrie's original Petrovsky plan was the right idea; she should have just kept him as a lovah. He's someone to keep her warm in the Manhattan winter and make love to by the fire. He isn't the kind of man you rewrite your entire life plan for, even if said plan is a charmed Parisian life.
Petrovsky is an artist who tries to sculpt the perfect doll out of Carrie clay. When he wants to play with his doll, he gives her pretty dresses and takes her on the town. But when he's too busy, he expects his Carrie doll to wait for him in the toy chest. It doesn't even occur to Petrovsky that Carrie exists outside of her relation to him. When the Carrie-doll has the audacity to express her anger at his behavior, Petrovsky's response is to hit her. Disgusting, but apropos for their relationship. His treatment of Carrie is nothing but a metaphorical slap in the face.
3 Best - Samantha & Smith
Samantha is a loud and proud manizer who has precious little time for monogamy. Her proclivity for casual sex is part and parcel because she likes it, and because it means not having to open up her heart. The few times she's done so resulted in absolute emotional disaster (see: Richard).
But Smith is different and not just because he's young and fabulous at role-playing. It's ironic that Samantha couldn't be less interested in finding a Prince Charming, yet here he is. Smith immediately forgives Samantha for her Richard relapse and stands by her side during her battle with breast cancer. He's truly worthy of meaning more to Samantha than any man she's ever known.
2 Worst - Carrie & Aidan
Aidan is a cad disguised in an ill-fitting jeans. To be fair, Aidan 1.0 wasn't a total nightmare. He was just boring and obviously not right for Carrie. Nobody blamed him for dumping her after learning of her affair with Big.
That should have been case closed. But then comes Aidan 2.0, gaslighter extraordinaire. His despicable treatment of Carrie is nothing short of psychological abuse. Any time she would call him out on it, whether he's being too nosy about her whereabouts or guilting her into going to his upstate hovel, Aidan just reminds her of his status as cuckolded victim. Calling off their engagement was the best decision Carrie ever made. No more Mr. "Nice Guy".
1 Best - Charlotte & Harry
Harry is the total opposite of Charlotte's fairy tale dream man. But she had that in Trey, and definitely didn't live happily ever after. So when the hairy Harry propositions Charlotte, she goes for it. Why not have some rebound fun?
She gets a lot more than she bargained for. For her entire life, Charlotte was putting herself in a cage, with her silly dating rules as the bars. With Harry, Charlotte can set herself free and it's with him that she finds real love and intimacy. She says goodbye to her WASP self figuratively and literally, converting to Judaism to marry him. His proposal at the synagogue singles night is easily the most romantic moment of the show. Are we willing to ship Charlotte and Harry as the show's best couple? Alrighty!