The 13 Most Embarrassing Boyfriends in Pop Culture

I believe in love! Just not with the kind of man who wears one dangly earring, trousers that sit too high on the waist, and who, after sharing a moment of intimacy, will look me in the eye and say, “Hey.” There are other things that make me uncomfortable, too. Like when men wear dressing gowns anywhere except a hotel room, when men like fizzy drinks, when men wear backpacks, and when men have games on their phone. But there is a simple ick—which, if you stick it out long enough, you can overcome—and then there is experiencing genuine, stomach-twisting embarrassment about even being in a relationship with a man.

The experience, as Chanté Joseph put it in her most recent piece for Vogue, is “culturally loser-ish.” “Being partnered doesn’t affirm your womanhood anymore; it is no longer considered an achievement, and, if anything, it’s become more of a flex to pronounce yourself single,” she wrote. “Where being single was once a cautionary tale (you’ll end up a ‘spinster’ with loads of cats), it is now becoming a desirable and coveted status, another nail in the coffin of a centuries-old heterosexual fairytale that never really benefitted women to begin with.” Isn’t that a more thrilling prospect than, I don’t know, being with someone who breaks up with you via a Post-it note or sparkles every time he steps out into the sunlight?

The world is awash with cringe-making men, and the entertainment industries have long taught us how to spot them. Here, a guide to the biggest losers in pop cultural history.

Jack Berger, Sex and the City