Ranking 12 Of The Most Toxic TV Boyfriends

Television romances often start with chemistry and charm, but some relationships reveal their cracks fast.

Control hides behind affection. Jealousy gets framed as passion.

Apologies arrive without real change. Over time, certain boyfriends leave emotional damage that outweighs any grand gesture or romantic speech.

What makes these characters unsettling is how familiar their behavior feels. Writers often give these men enough appeal to keep relationships going, even as warning signs pile up.

Ranking the most toxic TV boyfriends means looking beyond dramatic moments and focusing on patterns. Repeated behavior matters more than one bad night.

Disclaimer: This ranking reflects editorial opinion and interpretation of on-screen relationship dynamics, not definitive fact, universal consensus, or a clinical assessment of “toxic” behavior.

1. Ross Geller From Friends

Jealousy wrapped in humor might seem harmless at first glance, but Ross takes possessiveness to uncomfortable levels throughout Friends.

His infamous “we were on a break” defense shows how he dodges accountability when things get messy.

Watching him obsess over Rachel’s male coworkers or throw tantrums about her career success feels less like comedy and more like control issues dressed up as insecurity.

His pattern of making everything about his feelings, regardless of what his partners need, reveals emotional immaturity that never quite grows up.

2. Dan Humphrey From Gossip Girl

Brooklyn’s so-called moral compass turns out to be anything but trustworthy when you peel back the layers.

Dan positions himself as the outsider with integrity, yet he secretly runs Gossip Girl while judging everyone else’s choices.

His nice guy routine masks serious manipulation and boundary violations.

Recording his girlfriend’s private moments and broadcasting them to the entire Upper East Side crosses lines that apologies can’t uncross.

3. Ezra Fitz From Pretty Little Liars

Teachers dating their students isn’t romantic, it’s a massive power imbalance that Pretty Little Liars tried to glamorize.

Ezra knew exactly how old Aria was and pursued her anyway, which raises every red flag imaginable.

His secret surveillance and research into the girls’ lives, disguised as writing a book, shows calculated deception rather than genuine affection.

The show tried framing their relationship as true love, but stripping away the soft lighting reveals manipulation and inappropriate behavior that would have serious real-world consequences.

4. Ben Linus From Lost

Calling Ben a boyfriend feels generous considering how he weaponizes emotional connection for strategic gain.

Every relationship he forms serves some larger manipulation, with trust treated as just another expendable resource.

His relationship with Juliet showcases psychological control masked as protection and community.

Ben’s ability to make people question their own reality while presenting himself as their only ally defines gaslighting at its finest.

5. Rory Gilmore’s Boyfriends: Dean, Jess, And Logan

Why pick one toxic boyfriend when you can showcase three different flavors of relationship dysfunction?

Dean’s possessiveness erupts whenever Rory shows independence, complete with public meltdowns and guilt trips.

Jess brings emotional unavailability and communication issues wrapped in a bad boy package.

Logan rounds out the trio with entitlement, privilege, and an assumption that money solves everything.

Poor Rory navigates control issues, emotional immaturity, and partners who prioritize their own needs throughout her dating journey on Gilmore Girls.

6. Don Draper From Mad Men

Charm becomes dangerous when paired with chronic dishonesty and emotional withdrawal.

Don’s entire existence is built on lies, starting with his stolen identity and extending to every relationship he touches.

His pattern with women follows a predictable cycle: pursuit, conquest, emotional distance, betrayal, repeat. Betty, Megan, and countless others experience the same treatment.

Don uses romance and grand gestures to avoid genuine vulnerability, keeping everyone at arm’s length while maintaining the illusion of intimacy through his carefully crafted persona.

7. Chuck Bass From Gossip Girl

Volatility gets romanticized as passion throughout Chuck and Blair’s relationship, but rewatching reveals deeply troubling patterns.

His controlling behavior, emotional manipulation, and cycles of harm shouldn’t be mistaken for true love.

Trading Blair for a hotel demonstrates how he views people as possessions rather than partners. The show frames their toxicity as epic romance, complete with dramatic music and Manhattan skylines.

However, stripping away the glamorous packaging reveals emotional abuse, possessiveness, and a relationship built on power plays rather than mutual respect.

8. Derek Shepherd From Grey’s Anatomy

McDreamy’s nickname hides some seriously problematic behavior beneath those perfect hair and charming smile.

Derek’s pattern of emotional punishment whenever Meredith makes choices he disagrees with reveals controlling tendencies.

His career always takes priority, yet he resents when Meredith focuses on her own professional growth. The power imbalance between attending and intern evolves but never fully disappears.

9. Spike From Buffy The Vampire Slayer

Obsession wearing the mask of devotion defines Spike’s early relationship with Buffy, crossing boundaries that even vampire status can’t excuse.

His inability to accept rejection leads to increasingly disturbing behavior.

Though the character eventually grows and seeks redemption through getting his soul back, the journey there includes serious violations.

10. Nate Jacobs From Euphoria

Fear shouldn’t be part of any romantic relationship, yet Nate weaponizes intimidation against every person he dates. His obsessive need for control manifests through violence, manipulation, and psychological terror.

Maddy and Cassie both experience his explosive anger and possessive behavior firsthand.

Euphoria doesn’t glamorize Nate’s actions; the show clearly presents him as dangerous and abusive.

Watching his relationships unfold serves as a stark reminder of how abuse can hide behind popularity and athletic success.

11. Joe Goldberg From You

Romantic internal monologue can’t disguise stalking, obsession, and murder, though Joe certainly tries throughout You.

His ability to justify horrific actions through twisted logic about love makes him terrifyingly realistic.

Monitoring someone’s every move, breaking into their home, and eliminating anyone he perceives as a threat isn’t devotion. It’s criminal behavior dressed up in literary references and self-deception.

The show brilliantly exposes how abusers rationalize their actions while viewers see the truth.