10 Worst Romantic Comedies with Toxic Relationships
Romantic comedies are supposed to leave you smiling, with love stories that spark joy and warm the heart. But some miss the mark, showcasing relationships so unhealthy they make you question the whole genre.
These films, filled with troubling dynamics, turn romance into cringe-worthy dysfunction. Here’s my list of the 10 worst romantic comedies with toxic relationships, counting down from the least problematic to the absolute worst.
10. The Ugly Truth (2009)
Gerard Butler plays a crude TV host schooling Katherine Heigl’s producer on dating. The setup promises banter, but their dynamic thrives on manipulation and misogynistic advice.
The film pushes outdated gender stereotypes, and the romance feels forced. It’s a comedy where the laughs are overshadowed by uncomfortable power plays.
9. Made of Honor (2008)
Patrick Dempsey’s playboy tries to win over his best friend, played by Michelle Monaghan, as she plans her wedding. His scheming to sabotage her engagement feels selfish, not romantic.
The characters’ lack of honesty and respect undermines the charm. It’s a rom-com that mistakes deception for devotion.
8. My Super Ex-Girlfriend (2006)
Uma Thurman’s superheroine seeks revenge on Luke Wilson after a breakup. The premise could be fun, but her obsessive, controlling behavior crosses into unsettling territory.
The humor falls flat, and the toxic dynamic feels more creepy than comedic. It’s a film that tries to laugh off serious red flags.
7. Overboard (1987)
Kurt Russell tricks an amnesiac Goldie Hawn into believing she’s his wife to exploit her labor. The premise, played for laughs, is built on lies and manipulation.
Despite the real-life chemistry between the leads, the story glorifies deceit. It’s a dated comedy that hasn’t aged well.
6. What’s Your Number? (2011)
Anna Faris hunts down past boyfriends to find “the one,” guided by Chris Evans’ shallow neighbor. Their relationship hinges on judgmental attitudes and superficial advice.
The film’s obsession with sexual history feels toxic, and the romance lacks depth. It’s a comedy that leans on stereotypes instead of heart.
5. How to Lose a Guy in 10 Days (2003)
Kate Hudson and Matthew McConaughey play a writer and an ad exec manipulating each other for career goals. Their mutual deception makes the romance feel like a game of betrayal.
The charm of the leads can’t mask the unhealthy foundation. It’s a rom-com where love feels more like a prank.
4. He’s Just Not That Into You (2009)
This ensemble film follows multiple couples, many stuck in manipulative or dismissive dynamics. From stalking exes to cheating partners, the relationships glorify unhealthy behavior.
The star-studded cast, including Ben Affleck and Scarlett Johansson, can’t save the preachy tone. It’s a film that mistakes drama for romance.
3. The Bounty Hunter (2010)
Gerard Butler’s bounty hunter tracks his ex-wife, played decisions to exploit her for a job. The constant bickering and revenge tactics feel abusive, not funny.
The leads’ chemistry is nonexistent, and the plot romanticizes control. It’s a rom-com that leaves you rooting for no one.
2. 50 First Dates (2004)
Adam Sandler pursues Drew Barrymore, who has memory loss and forgets him daily. His persistence, while sweet on paper, often feels like manipulation of her condition.
The comedy glosses over ethical issues, making the romance uneasy. It’s a film that prioritizes gags over genuine care.
1. Twilight (2008)
Kristen Stewart’s Bella and Robert Pattinson’s vampire Edward define toxic love, with his controlling behavior and her obsessive devotion. Stalking and emotional manipulation are framed as romantic.
The film’s massive popularity can’t hide its unhealthy dynamic. It’s a romance that sets a troubling standard for relationships.
Which of these rom-coms made you cringe the most, or is there another toxic love story I missed? Share your thoughts in the comments!