8 "Cringy" 90s Rom-Coms That Aged Horribly

1. The Beautician and the Beast (1997)

Fran Drescher's role in The Beautician and the Beast wasn't enough to save this movie from its heavy-handed clichés. In the story, Fran plays Joy Miller, a beauty school teacher mistaken for an academic who gets whisked away to tutor the children of an Eastern European dictator named Boris.

It's clear the rom-com was trying to channel energy from The Sound of Music and Beauty and the Beast, but the result isn't nearly as endearing. The forced romance between Fran and Boris feels unearned, and the portrayal of Boris borders on offensive.

2. My Father the Hero (1994)

This film stars Gérard Depardieu as a clueless father who gets dragged into his teenage daughter's very uncomfortable plan to impress a boy. During a tropical vacation, 14-year-old Nicole, played by Katherine Heigl, decides the best way to seem more mature is to tell everyone that her dad is actually her much older lover.

The premise feels more creepy than anything since the movie crosses too many lines in an attempt to be funny. Instead, this "coming-of-age" rom-com took a wrong turn into uncomfortable territory.

3. Love Stinks (1999)

Love Stinks is one of those films that tried to channel the chaos of love gone wrong but served up a trope-filled mess instead.

French Stewart plays Seth, a sitcom writer who quickly regrets moving in with Chelsea, portrayed by Bridgette Wilson, after spending the night with her. So, what starts as a one-night stand spirals into lawsuits, sabotage, and over-the-top gender stereotypes.

The film leans heavily on clichés like the "crazy girlfriend" and the "commitment-phobic man" without offering any fresh perspective, making it pretty cringeworthy in 2025.

4. Never Been Kissed (1999)

Drew Barrymore might've carried Never Been Kissed at the box office, but the plot would raise more than a few eyebrows today.

She plays Josie Geller, a 25-year-old reporter who goes undercover as a high school student to write an exposé and ultimately falls for her English teacher. Meanwhile, her brother also enrolls to help her blend in.

Sure, Never Been Kissed attempted to explore themes of self-acceptance and second chances, yet it's hard to ignore the weirdness of adults mingling in a high school setting and the teacher-student romance subplot.

5. Housesitter (1992)

In Housesitter, Goldie Hawn plays Gwen, who sleeps with a recently-dumped architect named Newton, then moves into his dream house (meant to be shared with his now-ex fiancée) and pretends to be his wife without permission. And rather than calling the cops, Newton actually plays along in exchange for social and professional perks.

The movie banks on the chemistry between Goldie and Steve Martin, who plays Newton, but the whole plot is built entirely on lies and deception, which just wouldn't bode well today. In real life, Gwen's behavior would likely lead to a restraining order, not romance.

6. Blast from the Past (1999)

While the '90s have become infamous for some strange premises, Blast from the Past might just be one of the weirdest.

Brendan Fraser plays Adam, a man raised in a fallout shelter by survivalist parents. Then, when he finally ventures into the modern world, he meets Eve, played by Alicia Silverstone, who helps him adjust and winds up falling for him.

The plot of Blast from the Past is both far-fetched and unsettling. The idea of a man emerging after spending three decades underground and finding love in a few days is hard to take seriously.

7. Clueless (1995)

Of course, Clueless was iconic, and yes, it defined a whole generation. But if we're being honest, it hasn't aged as gracefully as some might claim.

Alicia Silverstone's Cher may have had the best wardrobe of the '90s, yet the story still ends with her falling for her ex-stepbrother, played by Paul Rudd, in a romantic twist that doesn't sit right today.

Additionally, the film leans on a lot of shallow stereotypes, with characters being defined by their looks, wealth, or social status. Its satirical tone makes some of that forgivable, but there's still no denying that certain jokes and gender norms in Clueless are now outdated.

8. 10 Things I Hate About You (1999)

Lastly, despite 10 Things I Hate About You often being praised for its witty dialogue and standout performances delivered by Julia Stiles and Heath Ledger, the story's core plot has aged like milk.

Why? It hinges on manipulation. A guy pays another guy to date a girl so he can date her sister. That setup alone strips the female characters of any agency or autonomy, casting them as obstacles as opposed to people.

Plus, even though Kat's tough exterior is slowly chipped away, it's not due to a genuine connection; instead, she's being wooed under false pretenses.

There are some heartfelt moments in 10 Things I Hate About You, but this rom-com's reliance on deception definitely makes it feel less empowering today than it may have in the '90s.