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
This is hugely hypocritical of me, seeing as I broke up with my first-ever boyfriend by passing him a note during our Year 8 English class. But apart from Berger ending things with Carrie via Post-it, there’s nothing more icky than a boyfriend plagued by jealousy over his partner’s success. —Julia Storm
Nate Cooper, The Devil Wears Prada
Imagine your girlfriend being a baddie with silky hair, and instead you’re pissed off that she was late to a few drinks. Sad! Much has already been said about Nate being the “real villain” of The Devil Wears Prada, but I personally think he’s not villainous, per se—that accolade surely goes to Miranda Priestly—he’s just a bit embarrassing, which is infinitely worse. —Daisy Jones
Edward Cullen, Twilight
I’ll preface this by saying I am not a Twilight girlie. I was very much on the High School Musical and Zac Efron side of the internet when the vampire series debuted in 2008. However, I will say, Edward Cullen is a strong contender for being a very embarrassing boyfriend. I mean, the man literally sparkles. —Hannah Daly
Josh Daniels, The Mindy Project
Mindy Lahiri’s boyfriends are a hit list of what not to look for in a partner; she likes them toxic and in close vicinity. That doesn’t mean the myriad ways they choose to embarrass her are warranted, however. Most heinous? Josh. A serial cheater who can’t stop negging her, he, in a word, sucks. —Morgan Fargo
Jeremiah Fisher, The Summer I Turned Pretty
Much of this summer was dominated by The Summer I Turned Pretty—both in the Vogue office and online—and, surely, Jeremiah takes the cake. First, he cheats on Belly; then he proceeds to make it up to her by buying her the world’s smallest engagement ring. He also throws a hissy fit when Belly tries to buy a cheaper chocolate cake for their wedding rather than his dream “two-tier, dark chocolate cake with a raspberry coulis filling and a mirror glaze,” and proceeds to lecture his fiancée on the delicate intricacies of a cacao bean. She did right by choosing the older brother. —H.D.
Mr. Collins, Pride and Prejudice
There’s passive aggression and there’s Mr. Collins reading sermons well into the night by the Bennet family hearth. Sort of promised to Elizabeth, sort of just a cousin-shaped nuisance, Mr. Collins is embarrassing for his sheer inability to let women speak. To then marry Elizabeth’s best friend as a pseudo-consolation prize is the nail in the coffin. Next! —M.F.
Alexander Hamilton, Hamilton
Does it get any more embarrassing than your husband declaring to the world that he cheated on you to dodge fraud allegations? Alexander Hamilton—in the Hamilton musical portrayal, at least—is peak embarrassing boyfriend. When he proposes to Eliza, he caveats it with how broke he is. He’s in love with his wife’s sister. He cheats on them both with another woman. Come on, man. —Riann Phillip
Samuel Maleski, Anatomy of a Fall
The whole premise of 2023’s Anatomy of a Fall revolves around a woman trying to clear her name when accused of killing her husband. Every aspect of her life and their relationship is put under a microscope in court, revealing Samuel’s deep insecurities about Sandra’s career. I don’t condone violence, but maybe he had it coming. —R.P.
Ross Geller, Friends
Like deciding whether you were a Carrie or a Samantha, horoscoping your ideal Friends boyfriend was a rite of passage for any ’90s or aughts teen. Did you want the wise-cracking Chandler or the lothario with a heart, Joey? Well, it turns out they were all awful—but perhaps the most embarrassing of the lot? Ross. Setting aside his cringe-worthy vanity (see: the gelled bouffant and TOWIE-worthy teeth whitening), Ross might not have his mates’ glaring red flags, but his misdemeanours have a distinctly contemporary flavor. From correcting everyone’s grammar and making Rachel feel bad about her career to freaking out over the male nanny, he’s one step away from the manosphere. All that was left was to form a problematic relationship with a student…oh, wait. —Joy Montgomery
Dan Humphrey, Gossip Girl
The original performative male (tote bag, notebook) who turned out to be the stalker-narrator of the Upper East Side, Dan spent six seasons of Gossip Girl judging everyone for their privilege while simultaneously cleaving his way into their world, dating multiple women he resented, and then—plot twist!—revealing that he’s been secretly live-blogging the most intimate details of their lives for years. Imagine finding out your boyfriend has been chronicling your every move all in the name of wanting to be “a writer.” Lonely Boy, indeed. —Daniel Rodgers
Aaron Samuels, Mean Girls
From the Lego-man hair to the perfectly groomed caterpillar brows, Aaron Samuels was the platonic form of the aughts dreamboat boyfriend. Yet fast-forward 20 (!) years, and what we once considered swoon-worthy now just seems plain annoying. Dating the head Plastic and then judging Cady for wanting to be one? Annoying. Mansplaining calculus and throwing a tantrum when Cady slips out the smallest Regina-ism? Embarrassing. I think we all know who the real diva is around here, Aaron. —J.M.
Michael Scott, The Office
Michael can’t believe he’s secured Jan—his hot boss he’s been pining after since day one—and when he finally enters a relationship with her, he fumbles the bag almost immediately. Jan wants to keep their relationship a secret under the guise of professionalism, but really, I think she just couldn’t stand the guy. —R.P.
Elon Musk, X
What are the chances that the richest man in the world would also be the cringiest? Or maybe the two facts are related—I don’t know. Either way, this guy, who is hoarding $482 billion and yet spends his time sharing 2016-era memes and retweeting Tommy Robinson, is easily the most embarrassing boyfriend to have ever lived. He automatically lowers the aura of anyone he dates, showing that all the money in the world—quite literally—cannot buy you even one ounce of rizz. —D.J.