Top 20 Worst TV Boyfriends

“The Vampire Diaries” (2009-17)
Damon is either a sassy sarcastic king one wants to fix or a toxic and manipulative villain who should’ve stayed far away from his brother’s Stefan’s girlfriend. It pretty much depends on who you ask. We say Damon Salvatore isn’t just a bad boyfriend. He rarely values any of the relationships in his life. The fact he can’t back off his own sibling’s partner, despite the fact that Stefan puts himself on the line for Damon several times, is proof of his endless selfishness. Of course, if he had backed off, we wouldn’t have the series’ big love triangle. And fans wouldn’t swoon over those moments when he managed to not be totally awful.

“Gilmore Girls” (2000-07)
Years later, fans still argue over which one of Rory Gilmore’s boyfriends was the best. They might argue even more bitterly over which one was the worst. While Yale man Logan and bad boy Jess have their fans and haters, most viewers would agree that Dean is not the right guy. Though he can be caring and sweet, he’s insecure long before Jess enters the picture, and his temper is troubling at times. Sure, it’s not like Rory treats him that well either. They’re both young when they first start seeing each other, but they also make some of their worst mistakes together. Let’s not forget he cheats on his wife — that’s not a good boyfriend or husband!

“The Office” (2005-13)
Yes, Jim and Pam are endgame, and that’s more than enough reason to dislike her first fiancé. But Roy more than earns our hate. He’s a neglectful boyfriend to Pam all throughout the first seasons, and treats her and her office mates like garbage. When it comes to showing interest in her art, life, or literally anything she says, Roy is missing in action if not downright indignant. It isn’t all bad, though. He actually has one of the biggest character arcs in the series. By the end, he’s done a lot of growing up. When it comes to being Pam’s partner, though, he’s the worst.

“The Big Bang Theory” (2007-19)
Look, we love the adorably nerdy Sheldon Cooper as much as the next person, but you have to admit, he isn’t exactly prime boyfriend material. For one thing, he is very set in his ways, which can get hard to deal with. In general, Sheldon can seem pretty egotistical, and openly condescending to those he considers his close friends. Granted, he has made huge strides at being a better companion, but people with less patience than Amy would have walked away a LONG time ago.

“One Tree Hill” (2003-12)
No matter how dreamy Chad Michael Murray is in the role, it doesn’t really change the fact that his protagonist is often a morally self-righteous tool. Lucas Scott always expects more from the women in his life than he ever gives them. Cheating on his girlfriend Brooke with her best friend, Peyton — multiple times — is bad enough. But that’s not all. He also just makes an obnoxious show of his goodness one too many times. Indeed, the fact that he constantly acts like a good guy or victim whenever any girlfriend tries to hold him accountable makes it hard to root for him.

“Grey's Anatomy” (2005-)
He’s a touch more sensitive than a lot of his fellow interns, but that just makes his romantic faux pas even more upsetting. And George O’Malley messes up a lot. His constant pining after his friends, Meredith and Izzie, borders on obsessive. But when he finally does land a great girlfriend-turned-wife, he fumbles it so hard it’s a wonder he doesn’t leave Seattle Grace immediately. He betrays Dr. Callie Torres by constantly lying to her, taking her for granted, and ultimately cheating on her with Izzie. He also hides behind the fact that he isn’t as callous and abrasive as men like Alex Karev. If anything, that just makes him more of a disappointment.

“Girls” (2012-17)
This is another one of those situations where both of the people in a relationship are terrible for each other. All the characters’ narcissism becomes a huge part of the entire narrative arc of “Girls.” But Adam’s gracelessness and clear anger problems are on full display during some of Hannah’s lowest moments. Somehow, his aggression and constant lack of consideration for her feelings make even Hannah’s worst points seem forgivable at certain times. Even after he starts dating her friend, Jessa, it seems like he was almost destined to be the guy you spend years trying to heal from.

“Scandal” (2012-18)
Being President of the United States is a lot of pressure. Unfortunately, Fitz is as bad at politics as he is in his relationships. Not only does he seem completely oblivious or unwilling to see just how much Olivia Pope has sacrificed to put him in the Oval Office, but his sense of entitlement stinks up all of Washington D.C. It’s why Olivia’s attraction to him feels more like a bad habit than a true romance. It also adds an extra layer of grossness to him cheating on his wife with her. Olivia is as capable, clever, and underhanded as anyone in the capital. Hiding in his shadow is strategically advantageous for her. Unfortunately, his whiny entitlement and unearned heroism wears pretty thin.

“Gossip Girl” (2007-12)
Dan Humphrey may seem like a perfectly nice guy at first, yet he is anything but. We mean (and there’s a massive spoiler alert here, so cover your ears if you don’t wanna hear it), he actually turns out to be Gossip Girl! How can he not make this list? Dan is seemingly always causing issues, like, you know, full-on stalking people. Plus, the guy’s always putting the blame on others, like when he slept with Serena and when he broke-up with Blair. He puts on a nice guy façade while secretly ruining lives as Gossip Girl, and really, it doesn’t get much worse than that.

“Euphoria” (2019-)
The football jock’s crimes are far too numerous, evil, and YouTube-unfriendly to list here. But his constant mistreatment of his girlfriends, Maddy and Cassie, throughout the first and second seasons of the controversial HBO series just gets worse as it goes on. Hateful and violent, Nate isn’t afraid to lash out at anyone he dates. It’s fair to say that he didn’t exactly have the best chance at breaking the cycle, given his awful home life. Still, that’s really no excuse for his horrid behavior, especially when you consider how complicated everyone’s life seems to be on this show. Needless to say, his behavior easily ranks him as the worst boyfriend in the bunch.

“Gossip Girl” (2007-12)
Not only is he a terrible on-again off-again boyfriend to Blair Waldorf once they start seeing each other, but Chuck’s constant manipulations make him one of the show’s biggest overall villains. Indeed, the Upper East Side playboy proves himself to be a rotten, predatory person from the very first episode. Now, we know no one on “Gossip Girl” is a saint. And unfortunately, the show centering Chuck as one of the main characters means they have to be a little too forgiving of his crimes at times. But it’s hard to downplay his terrible traits. He literally trades Blair for a hotel in one episode. And then he has the nerve to act like a jerk when she’s rightfully upset about it? He’s unhinged.

“Supergirl” (2015-21)
Mon-El is a Daxamite prince who has come to Earth and eventually strikes up a relationship with Kara Danvers, AKA Supergirl. He comes from a race full of bullies, which is not surprising, given Mon-El’s penchant for brutal honesty and his abusive personality. Not to mention the fact that he seems like a coward. He makes Kara question herself, and her role in society, and often blames his own problems on her rather than looking inward. Perhaps he means well, but Mon-El is one extremely flawed dude.

“Shameless” (2011-21)
Throughout “Shameless,” Jimmy Lishman has two major relationships. One is with his true love, Fiona, and the other is with a mob boss’s daughter named Estefania, who uses him to attain immigration status. He constantly switches between the two women; and while he seems devoted to Fiona, he cheats on her with Estefania on numerous occasions. He is also a consummate liar, and is not shy about lying directly to Fiona’s face. He also hates family life with Fiona, and devolves into a whiny brat who cries about everything. He may mean well, but he’s a real selfish bastard.

“Friends” (1994-2004)
Let’s face it: Ross Geller is a horrible boyfriend. For one thing, he said the wrong name at his and Emily’s wedding! Yeah, we understand that he was still in love with Rachel, but come on, it doesn’t get much worse than that. He is also extremely quick to sleep with another woman after a fight and dumps girlfriends like they’re pieces of garbage. He’s also a massive jerk towards Rachel, calling her ditzy and not respecting her career; and he’s a needy, whiny, and possessive person who seems far too self-centered for his own good. Sorry, Ross. You may think you’re a nice guy, but you’re not. YEAH, WE SAID IT.

“How I Met Your Mother” (2005-14)
For the first few seasons, Barney Stinson was a consummate ladies’ man. He dressed well, bought drinks, and wooed women like there was no tomorrow. And while Barney later develops feelings, he is never the greatest boyfriend. He retains some semblance of misogyny, and in the early days with Robin, his careless, selfish, and relatively unloving attitude results in the pair devolving into horrible versions of themselves. He also blatantly lies to Nora about wanting kids, and cheats on her with Robin, and later distrusts Quinn to such a huge extent that they break up. He may mean well, but Barney is not boyfriend material.

“The Mindy Project” (2012-17)
Danny Castellano may mean well, but really, the guy is a huge jerk and he makes for one problematic boyfriend. For one thing, his temper definitely needs to be reeled in. He has a very short fuse and is constantly fighting with Mindy over anything and everything. He also has a huge problem with commitment and manipulates those around him. Despite this, he and Mindy get together, where in turn he treats her with disrespect and tells her to give up her career. So yes, his heart is in the right place, but Dan is nevertheless a problematic dude.

“The Office” (2005-13)
We like early “Office” Ryan. He’s quiet and keeps to himself. And while he seems distant towards the obviously-flirtatious Kelly, he seems like a good enough guy. And then . . . he gets a little too big for his britches. After crashing in the corporate job, Ryan convinces Kelly to break-up with Darryl, only to leave her behind when he goes to Thailand (or, more accurately, Fort Lauderdale). They are also extremely hostile towards each other throughout much of the series, and Ryan seems to openly hate being with her. Kelly isn’t exactly a great girlfriend, but then again, Ryan isn’t exactly a great boyfriend. It’s one of TV’s most incompatible relationships, and while we love watching it, we wouldn’t recommend dating him.

“Sex and the City” (1998-2004) & “And Just Like That...” (2021-)
The Notorious Biggie is arguably the quintessential mega-jerk boyfriend. Throughout his relationship with Carrie, he is extremely distant with her, repeatedly failing to become more intimate. He has a “Big”-time commitment problem. Now, this commitment phobia wouldn’t be so bad . . . if it weren’t for the fact that he marries another woman after only five months of dating, and absolutely shatters Carrie’s self-confidence. But wait, there’s more! He also pines after her once he’s married, and the two eventually begin an affair. They end up together, but at what cost? Perhaps it’s no surprise that when he died on “And Just Like That…”, no one was all that upset about it — except maybe the people at Peloton.

“Orange Is the New Black” (2013-19)
Whoo boy, where do we even start with Larry Bloom? While Larry is at first quite supportive towards Piper’s life in prison, things quickly turn sour. He generally doesn’t seem to care about her problems, and even uses them as the basis for an article to further his own career. He also goes on radio shows to discuss the inmates, and attain a semblance of fame himself. Plus, after he and Piper break up, he’s intimate with her best friend in their house, which then causes the latter to leave her husband. Larry is nothing but a destructive force who will roll over anyone for his own happiness.

“You” (2018-)
No one on this list is quite as charming and dangerous as Joe Goldberg. He’s a stalker and murderer who treats romantic relationships like undercover operations. He’s a trained agent — efficient, enigmatic, and endearing in the way he burrows his way into his target’s heart. The scariest thing is that, in his own twisted mind, he thinks he’s doing it all out of love. Being with Joe typically means meeting an early end. Whether it’s because the woman finds out all he’s done to manipulate her, like Beck, or because she tries to go toe to toe with him like Love, entanglements with him usually end badly. If one does manage to escape like Marienne, it won’t be without serious trauma.