Every Man on Sex and The City Sucks, Actually

A deep dive on the worst of the worst: part one.

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Even I’m surprised it took me this long to watch Sex and The City. Over the years I’d seen episodes here and there, but every attempt to watch the series in full always petered out after a couple episodes — to be honest, I just got bored. I’ve seen the first of the two movies, which is only okay in my opinion — but I will always love a fashion montage, and Carrie trying on all those couture wedding dresses is still one of the best in recent memory.

But the series’ perma-presence on my TikTok For You Page started to intrigue me. After seeing the one-liners, the drags, and the reimaginings of the characters if they were in their early thirties today, I couldn’t help but wonder…what was in this show that made it have such a hold on three generations of women, 25 years after its release? So I finally sat down to start the series–and finish it— at the end of last year, and while I’m still working my way through the show’s final two seasons, my prevailing thought is this: wow, every man on this show sucks, actually.

I had already despised Mr.Big from his conduct in the movie, but watching the series makes me realize that he’s perhaps one of the most wicked men ever written. And now, with more context on the early stages of their relationships, I also see that “good guys” Harry, Charlotte’s husband, and Steve, Miranda’s now-ex husband (if you consider the reboot And Just Like That… canon, which many devoted fans of the original series do not — I haven’t seen it outside of clips being dragged on social media), are also literally villains. Like, it’s actually quite shocking to see lol — especially because they’re both so romanticized by the fandom.

So naturally I had to do a deep dive on the worst of the worst (if I ranked every man we’d be here all year) — and what we can learn from the women’s long term relationships. This post covers seasons 1-3,  and I’ll be back early next month with Part Two since, at present, my already scant TV watching time is being eaten up by the all the Oscar movies I need to watch so I can keep up in conversation with all my Serious Film Friends who actually have grown-up taste instead of rewatching the same five movies teen movies from the ‘90s, which is how I prefer to spend my time. 

I will be ranking the men on a scale of one to three 🤮 emojis.  A single 🤮 represents your garden variety menace who’d be terrorizing women on Hinge today (as an example: a forty-year-old who’s “not sure” what he’s looking for in a relationship but also “wants kids”). Three (🤮🤮🤮) means the man is a scoundrel so demented he should be terrorizing Gotham City in a clown suit. Mr.Big, even in just the first three seasons, is so noxious that he exists outside the scale entirely, but we’ll get there when we get there.  This is a long one, so make yourself a cup of tea (or pour a glass of wine, if you’re not doing dry January) and settle in for the read. 

Let’s get into it:

The Rankings

SAMANTHA

Samantha Jones, the chronically insecure sex pot played with stunning charisma by Kim Cattrall, has only one real relationship in the first three seasons of the show. James, this first boyfriend, is a perfectly nice man afflicted with a micropenis – so you can guess what causes their breakup. But she still messes with a few freakshows, who I’ve ranked below.

Thor: 🤮🤮

Thor hard at work — if this show was out today, this would be product placement for Gilette.

Thor is a fitness instructor Samantha hooks up with in season two who gets off on shaving her pubes into the shape of a lightning bolt which – sure! Between two consenting adults this is fine – far be it from me to yuck someone else’s yum – but what makes Thor truly nasty is that apparently this post-sex landscaping session is his go-to move. (Kind of a strange kink, but go off king!) Another one of his partners who thought they were exclusive finds out that he’s sleeping with other people at the gym sauna, when she sees that she and Sam are sporting matching bush bolts. Twinsies!

Barkley: 🤮🤮🤮

In the second episode of the series, Sam sleeps with Harvey Spector, Barkley, an “artist” who’s a modelizer: a yucky brand of New York City man who collects models like baseball cards for the approval of other men. Immediate ick, but Barkley takes things further by secretly filming these sexual encounters with models without their consent – which neither Carrie nor Samantha is repulsed by upon learning this information. Samantha’s turned on by it, asking him to film her when they sleep together. He declines at first – that particular honor’s only for models – but gives in when Sam insists, satisfied to be elevated to model status by this random unemployed creep. Ugh. 

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CHARLOTTE

Trey:🤮

Trey is Charlotte’s first husband. A cardiologist with longgg family money, Trey’s the kind of perfect guy Charlotte always envisioned herself with, and they fall fast and hard after meeting in season three. But the veneer of perfection is soon cracked when she meets Bunny, Trey’s emotionally incestuous mother, a passive aggressive Connecticut WASP witch of the highest order. (I went to middle school in Connecticut with these types, so when I say I was forged by the flames, I’m not kidding.) For further context, Bunny is the type of woman who insists on bonding with her nearly forty-year-old son during “bath time,” so yeah…bizarro. 

But even if you set aside the manipulative mother, Trey’s passiveness and conflict avoidance make him a terror. When he and Charlotte are about to get married and his impotence is revealed, he simply wants to stick his head in the sand and ignore the issue entirely, expecting Charlotte to accept a sexless marriage while he nurtures a secret masturbation habit fueled by a porn addiction that heavily implies that he’s not physically attracted to her. (Charlotte finds his large stash of Juggs magazines – and notably, Charlotte is fairly Jugg-less)

What keeps Trey at only one vom is his behavior when he and Charlotte eventually divorce in season five, which I’m currently watching. While Bunny wants to make sure Charlotte walks away with nothing, Trey writes a letter in her defense stating that she was an exemplary wife and should get whatever she wants in the divorce proceedings – including $2 million and their massive prewar Park Avenue apartment that’s been in his family for generations. He’s a good man, Savannah!

I want to linger here a moment to talk about what we can learn from Charlotte and Trey, a lesson I walked away from one of my own relationships with: if something’s off, more commitment isn’t going to make it any better. In fact, the increased commitment will only introduce more pressure into the situation, bringing it from merely uncomfortable to truly unbearable.