The most awkward boyfriends in pop culture Now it's really embarassing

Recently, people have been talking far and wide about boyfriends. Or rather, about the very act of having a boyfriend. Has it become embarrassing? Or is it embarrassing to show him on social media, almost as if he were a status symbol? As we grow increasingly self-aware, the narrative around love is changing too. We’re learning to recognize a red flag when we see one (almost always, let’s be honest), but also to appreciate new and different models of masculinity. We keep a safe distance from performative males and analyze our relationships with greater clarity. Have we become infallible, then? Absolutely not. We’ll keep falling into the traps of self-centered men who make us feel special, believing words we know deep down aren’t true, and giving time to people who don’t deserve it.

The embarrassing boyfriends of pop culture

Despite all our efforts, the world is still full of men who are not worthy of our attention. And you’d think pop culture would have taught us how to spot them by now. Over the years, movies and TV shows have given us boyfriends so problematic they feel like parodies. Characters who should have been warnings, not role models—and who should have taught us exactly which kinds of men to stay away from. With a mix of critical insight and irony, we’ve selected 8 decidedly embarrassing boyfriends from pop culture. The kind that could have saved us from many mistakes, if only we had taken them seriously.

Dan Humphrey, Gossip Girl

For six seasons of Gossip Girl, Dan watched and judged Manhattan’s elite from a position of moral superiority (from the depths of his Brooklyn loft). Meanwhile, he dated several women from that world and - most importantly -exposed their darkest secrets without worrying about hurting the feelings of the people supposedly closest to him. Behind the façade of the sensitive outsider lies a boyfriend who turns every relationship dynamic into narrative material. And he’s convinced he’s entitled to everything because “he’s not like the others.” Spoiler: he is.

Ross Geller, Friends

A paleontologist, yes. Evolved? Not quite. The archetype of the insecure man, he presents himself as the nice guy next door while carrying a heavy load of unjustified jealousy, mansplaining, and a constant need to be right. Taking responsibility is not exactly one of his strongest skills, as the mantra “We were on a break” constantly reminds us. Ross never hurts people out of malice, but out of a disarming lack of self-awareness. And that’s precisely what makes him so dangerously embarrassing.

Nate Cooper, The Devil Wears Prada

We’ve said it again and again, in hindsight: the real villain of The Devil Wears Prada is not Miranda Priestly, but Andy’s boyfriend. Frustrated by his own lack of success, he unloads all his unfulfilled ambitions onto his partner, making her feel constantly guilty for a job that already pushes her to the limit. When it comes to being a team player—men, do not learn from Nate.

Jeremiah Fisher, The Summer I Turned Pretty

It’s rare in pop culture history to see such a united front against a character. And yet, it happened with Jeremiah, one of the protagonists of The Summer I Turned Pretty, caught in a love triangle with his brother Conrad and Belly. The perfect stereotype of the golden retriever boyfriend, behind his puppy-eyed charm Jeremiah hides the emotional intelligence of a dessert spoon, childish demands (let’s just say mirror glaze cake…), and an extremely poor ability to take responsibility. After all, who wouldn’t try to fix cheating with a marriage proposal without a ring, no less?

Christian Grey, Fifty Shades of Grey

Christian Grey is the product of a massive collective hallucination. Manipulative, jealous, and obsessive, he embodies all the worst traits one can find in a man, romanticized by helicopter rides and tailored suits. His idea of love is an exercise in control, and rather than dominant, he comes across as deeply insecure. Embarrassing? Yes—almost as embarrassing as having found him even remotely attractive for a minute.

Edward Cullen, Twilight

“And so the lion fell in love with the lamb. What a stupid lamb, what a sick, masochistic lion.” The cringe factor that Edward Cullen is capable of generating is perfectly summed up in this line, which has lived rent free in my head for over 15 years. He shows up in your bedroom uninvited, watches you sleep, and follows you everywhere: in 2008 it seemed romantic, today it would be a case study in consent and boundaries. Add his tendency to literally sparkle, and he’s definitely not the guy I’d introduce to my parents.

Mr. Big, Sex & The City

Mr. Big is the man who turned emotional unavailability into a luxury aesthetic. Charming, brilliant, magnetic—but always one step behind when it comes to taking responsibility. He’s the boyfriend who disappears, comes back, and still expects to be understood. His relationship with Carrie is a masterclass in mutual idealization and terrible timing. Big isn’t evil: he’s simply incapable of truly showing up.

Ken, Barbie

Ken is just Ken: a decorative boyfriend, devoid of personality, talents, or goals. He exists solely in relation to Barbie, and in his one brief attempt at self-determination - the Mojo Dojo Casa House - he tries to resurrect a model of masculinity already destined for extinction. He’s useless, but at least harmless. The same cannot be said for some Kens we’ve unfortunately encountered in real life.