10 Worst TV Boyfriends Who Made Us Fall Out Of Love

Bill Compton in True Blood

At first, Bill Compton felt like the ultimate mysterious boyfriend. Polite, charming, protective, all very swoon-worthy. But the longer True Blood went on, the more uncomfortable his relationship with Sookie became. His idea of “protecting” her slowly turned into controlling her choices and keeping secrets. Then came the reveal that their romance wasn’t even fully genuine to begin with, which made everything worse.

Xander Harris in Buffy the Vampire Slayer

Xander Harris always felt like the guy you wanted to root for until he kept messing things up. Over and over. He struggled with jealousy, insecurity, and a tendency to take the women in his life for granted. Whether it was Buffy, Willow, Cordelia, or Anya, Xander rarely showed real emotional growth. Leaving Anya at the altar was the breaking point for many fans.

Ross Geller in Friends

Ross Geller loved deeply, but his insecurity constantly got in the way. His jealousy and possessiveness made Rachel’s independence feel like a threat instead of something to celebrate. When things didn’t go his way, Ross shut down, got passive-aggressive, or made impulsive decisions. His obsession with Rachel also meant other people got hurt along the way. The infamous “break” situation summed him up perfectly; emotional, reactive, and unwilling to fully take responsibility.

Jimmy Lishman in Shameless

Jimmy entered Fiona’s life like a breath of fresh air; charming, attentive, and seemingly stable. But that didn’t last long. As their relationship deepened, his need to control things became obvious. He questioned Fiona’s choices, criticized how she handled her family, and slowly tried to pull her into depending on him. What made it frustrating was that Jimmy genuinely thought he was helping. He wasn’t. Fiona didn’t need fixing, she needed support.

Dean Forester in Gilmore Girls

Dean Forester started out as the perfect first boyfriend, which made his later behavior even more frustrating. As Rory grew more confident and ambitious, Dean grew more insecure. He struggled with jealousy and constantly needed reassurance, even when Rory did nothing wrong. His habit of pushing himself back into her life blurred boundaries and created unnecessary tension.

Mr. Big in Sex and the City

Mr. Big mastered the art of keeping Carrie close but never secure. Every time things seemed serious, he pulled back just enough to keep control. He avoided commitment, shared information when it suited him, and disappeared when emotional effort was required. Watching Carrie twist herself into knots trying to figure him out was exhausting. Mr. Big wasn’t openly cruel, which somehow made it worse.

Steve Harrington in Stranger Things, Season 1

We all love Steve Harrington now, but let’s be honest, early Steve was not it. He started off arrogant, judgmental, and way too comfortable putting others down. His relationship with Nancy showed just how insecure he really was. Instead of supporting her curiosity and intelligence, he reacted with jealousy and denial. And yes, the Barb situation still hurts.

Lucas Scott in One Tree Hill

Lucas Scott had a habit of talking like a romantic hero and acting like a confused mess. He made big promises, intense declarations, and then immediately complicated everything with bad decisions. His treatment of Brooke was especially painful; claiming she was “the one” while clearly still emotionally tangled with Peyton. Lucas avoided clear boundaries and left both women hurt and confused.

Ted Mosby in How I Met Your Mother

Ted Mosby loved love, maybe a little too much. He walked into relationships with a full plan already mapped out, then tried to squeeze people into it. Ted rushed milestones, ignored warning signs, and confused persistence with romance. His relationship with Robin showed this clearly, he loved her deeply but struggled to accept who she actually was.

Damon Salvatore in The Vampire Diaries

Damon Salvatore made being problematic look charming. Damon manipulated situations, crossed boundaries, and expected forgiveness without accountability. His relationship with Elena was intense but deeply unhealthy, built more on obsession than respect. Watching Elena constantly excuse his actions became frustrating over time.