Some TV boyfriends make us swoon, but others make us want to throw our remotes at the screen. From manipulative schemers to emotionally unavailable wrecks, these fictional guys have put their partners through the wringer.
Whether you love to hate them or just plain hate them, these characters sparked serious debates about what a bad boyfriend really looks like. Here are 17 of the most difficult TV boyfriends ever to grace our screens.
1. Nate Jacobs (Euphoria)
Controlling, obsessive, and flat-out terrifying — Nate Jacobs from Euphoria takes the top spot without much competition. He manipulated Maddy emotionally and physically, played mind games like it was his full-time job, and then turned around and toyed with Cassie’s heart too.
Nate never seemed to care about the damage he left behind. Watching him on screen is genuinely uncomfortable, which means the writing and acting both hit their mark perfectly.
2. Chuck Bass (Gossip Girl)
Chuck Bass wore designer suits and said romantic things, but underneath all that polish was someone who treated love like a business transaction. He once tried to trade Blair for a hotel — yes, an actual hotel — which is one of the most jaw-dropping moments in TV history.
He also physically attacked Blair after she announced her engagement to someone else. Chuck had moments of growth, but his worst behavior is genuinely hard to forget or excuse.
3. Dean Forester (Gilmore Girls)
Dean seemed like the perfect small-town sweetheart at first — tall, attentive, and totally devoted to Rory. But that devotion quickly turned into jealousy and possessiveness that made every scene with him feel a little suffocating.
He sulked when Rory spent time with others, gaslit her regularly, and later cheated on his wife to rekindle things with her. For a guy who played the “good boyfriend” card so hard, Dean had a lot of explaining to do.
4. Mr. Big (Sex and the City)
Mr. Big is basically the blueprint for emotionally unavailable. He strung Carrie along for years, married someone else while still tangled up with her feelings, and then — most infamously — stood her up on their wedding day.
Fans spent years debating whether Big was romantic or just plain selfish. Spoiler: it was mostly the latter.
He had charm for days, but charm does not make up for consistently choosing himself over the person he claimed to love.
5. Joe Goldberg (You)
Joe Goldberg is in a category all his own. He does not just have boyfriend red flags — he is the entire red flag parade.
A serial killer who frames his stalking and controlling behavior as deep, devoted love, Joe is genuinely terrifying precisely because he sounds so reasonable in his own head.
He eliminates anyone he sees as a threat to his relationships. The scariest part?
Plenty of viewers still found themselves rooting for him, which says a lot about how well-written the character really is.
6. Ross Geller (Friends)
Ross Geller spent a lot of time convincing himself he was the reasonable one in every conflict, but the receipts tell a different story. He said the wrong name at his own wedding, slept with someone else immediately after a “break” with Rachel, and then blamed her for it endlessly.
His jealousy over Rachel’s male coworkers was exhausting to watch. Ross had likable moments, sure, but his pattern of putting his ego above his relationships made him one of TV’s most frustrating partners.
7. Danny Castellano (The Mindy Project)
Danny Castellano started out as the grumpy-but-lovable foil to Mindy’s bubbly personality, and early on that tension felt fun. But as the seasons went on, his controlling tendencies became harder to laugh off.
He pressured Mindy to give up her career and become a stay-at-home mom, which felt like a betrayal of everything their relationship stood for. His short temper and manipulative streaks turned what could have been a great love story into something that left a lot of viewers frustrated and disappointed.
8. Ezra Fitz (Pretty Little Liars)
No matter how the show tried to romanticize it, Ezra Fitz dating his underage student was wrong — full stop. He was her teacher, in a position of authority, and the age gap made the relationship deeply inappropriate from the very start.
To make it worse, he had been stalking Aria and her friends to gather material for a true-crime book. The show leaned into the “forbidden romance” angle, but many viewers grew up and looked back realizing this storyline sent seriously troubling messages about power and relationships.
9. President Fitzgerald Grant III (Scandal)
Having the most powerful man in the world as your boyfriend sounds thrilling until you realize what it actually costs. Fitz kept Olivia Pope dangling with promises he rarely kept, expected her to sacrifice her career and reputation for him, and threw jealous rages when things did not go his way.
He used his presidential power to manipulate situations to his advantage in the relationship. Olivia deserved someone who lifted her up — Fitz mostly just complicated her life in spectacular, dramatic fashion.
10. Lawrence Walker (Insecure)
Lawrence Walker had all the ingredients to be a great partner — charm, good looks, and a genuine connection with Issa — but he kept finding ways to fumble it. He spent years coasting on potential while Issa carried the emotional weight of their relationship, never quite showing up the way she needed.
When things finally fell apart, he turned around and cheated on his new girlfriend with his ex. Lawrence is the kind of guy who always seems like he is almost there but never quite arrives.
11. Barney Stinson (How I Met Your Mother)
Barney Stinson turned being a bad boyfriend into an art form — complete with a literal playbook of tricks for manipulating women. He lied, cheated, and treated relationships as games to be won rather than connections to be nurtured.
Yes, he eventually grew and found real love, but seasons of genuinely awful behavior preceded that growth. Barney is a fascinating character precisely because the show made you root for him despite his long track record of being careless with people’s hearts and feelings.
12. Dan Humphrey (Gossip Girl)
The big Gossip Girl reveal changed everything about how fans viewed Dan Humphrey. He spent years playing the humble outsider while secretly running an anonymous blog that destroyed reputations, fueled insecurities, and manipulated nearly everyone around him — including the girls he claimed to care about.
The “nice guy” act was the most calculated move of all. Dan did not just have bad boyfriend tendencies — he architected emotional damage on a large scale while somehow keeping his hands appearing clean the entire time.
13. Tony Stonem (Skins)
Tony Stonem from the UK series Skins treated his relationship with Michelle like a social experiment. He cheated repeatedly, gaslit her when she called him out, and seemed to take genuine pleasure in watching her try to make sense of his behavior.
What made Tony so unsettling was how effortlessly charming he could be when he wanted something. He was the kind of person who could make you feel special and invisible at the same time — a truly exhausting combination for anyone trying to love him.
14. Jimmy Lishman (Shameless)
Jimmy — or Steve, or whatever name he was using that week — built his entire relationship with Fiona on a foundation of lies. He had a secret wife, a hidden criminal past, and a talent for disappearing exactly when Fiona needed him most.
Fiona Gallagher already had enough chaos in her life without adding a man who treated honesty like an optional accessory. Jimmy had real moments of sweetness, but his compulsive dishonesty made it nearly impossible to trust anything he said or did.
15. Damon Salvatore (The Vampire Diaries)
Damon Salvatore had brooding bad-boy energy dialed all the way up, and plenty of fans adored him for it. But stripping away the charm reveals a trail of genuinely horrifying behavior — killing Jeremy Gilbert, compelling Caroline without her consent, and treating violence as a default reaction to frustration.
His love for Elena was real, but love does not excuse the sadistic choices he made along the way. Damon is the ultimate example of a character the audience roots for even when they really, really should not.
16. Roy Anderson (The Office)
Roy and Pam were engaged for years, and in that entire time he showed almost no real interest in the things that mattered most to her. Her art, her dreams, her feelings — Roy treated all of it as background noise to his own comfort and routine.
He was not cruel in a dramatic way, which almost made it worse. The quiet, everyday neglect Roy showed Pam is a kind of difficult that many people recognize from real life, making him one of the more relatable cautionary tales on this list.
17. Aidan Shaw (Sex and the City)
Aidan Shaw had all the qualities that looked great on paper — he was warm, reliable, handy, and genuinely devoted to Carrie. Fans loved him for it, and many still argue he was the one she should have chosen in the end.
But Aidan had a judgmental streak that surfaced more as time went on. He made pointed comments about Miranda’s personal choices and criticized Carrie in ways that felt less like concern and more like control.
Being the “good guy” alternative does not automatically make someone an easy partner to be with.