19 Rom-Com Moments That Are So Dated, You'll Be Shocked They Happened During Your Lifetime

Times have changed...

Dear readers, I am 30. I've seen some things in my lifetime.

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I've consumed quite a few rom-coms in my days. Thanks to the streaming age, I can revisit some of these classics.

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Some are easier to revisit than others though because some of these are totally built on dated concepts or in dated settings that just would not happen today. From problematic to just outdated, these are the 19 rom-coms I feel wouldn't hold up today.


1. Bridget Jones' Diary was built on the foundation of single-shaming, which wouldn't fly today. Her feminism is also kind of pegged to the era, presenting a single woman who knew and was aware of sexual harassment but coyly said she didn't mind it.

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Chain-smoking is tres '90s, with today's BJ a serial vaper (or maybe an American Spirits holdout).

2. Chances Are had Robert Downey Jr. meeting a woman and falling for her, only to meet her mom and discover it was his wife and daughter from a past life. It's all kinds of problematic.

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3. There's Something About Mary was a rom-com heavily seasoned with gross-out humor that was such a '90s signature, but today? We'd probably pass.

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4. While You Were Sleeping's "in love with a stranger" premise would be seen as super creepy today, not to mention that her being a toll booth collector really plants this one in the '90s.

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5. How To Lose A Guy in 10 Days exists in a world where a print magazine is thriving, and their how-to column has a seemingly sizable expense budget...aka the early '00s.

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The Burberry dog sweater, crazy statements about gender norms, and use of landlines really seal the deal.


6. Clueless is tethered to '90s fashion in all the best ways. Credit cards and car phones really set the scene.

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Few people with 2022 eyes can look past the fact that Cher and Josh are stepsiblings as well.

7. Never Been Kissed is filled with early aughts fashion, enormous computers, books, board meetings without smart boards, and tons of other indicators it is from times passed.

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Adults posing as high schoolers and student-teacher relationships would also be frowned upon, to say the least.

8. An entire relationship based on emails? Sorry You've Got Mail, you'd be You've Got Swipes today.

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9. No one wants to get dumped by letter (and in 2022, no one does), but Addicted to Love takes it a step farther with a creepy stalking plot. It's supposed to be romantic, but it's definitely just unhealthy.

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10. Sleepless in Seattle happens around a radio call-in show. Today, it'd probably be a podcast or maybe a Twitch stream.

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11. Knocked Up being about getting pregnant from a one-night stand may make you think it can still hold up today, but take one look at the old-school cell phones and email outreach and you'll realize you're in yesteryear.

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Debbie would be tracking her husband's location to find out where he's really at when he says he's in the Valley instead of following him there.

12. What Women Want is one of many early aughts rom-coms that depends on an answering machine. What a time.

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And try to justify mind-reading as an acceptable form of consent in 2022, go ahead.

13. My Best Friend's Wedding wouldn't have had Julianne half as surprised by Michael's engagement because social media would be a thing.

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Also, very few weddings in today's world are planned on such short notice, a rom-com tool that changed the course of many films in the genre during that time.

14. Romeo + Juliet had a very '90s cinematography and retold a timeless story while making it feel like a period piece.

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15. Garden State walked so that...

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16. ... 500 Days of Summer could run in their very '00s glamorization of the manic pixie dream girl, a trope which is wildly problematic in retrospect.

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17. It would take about three seconds for the characters in One Fine Day to realize they switched cell phones.

18. Isabel Fuentes in Fools Rush In would learn everything about Alex Whitman in a quick Google search. The fashion is also super timely to the late '90s.

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19. Hitch operated on some pretty misogynistic rules of dating, and the soundtrack is super '00s.

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Need some more clues you're in the '00s? Ahem, speed dating.

What movies from your lifetime feel tragically dated? Open up in the comments!

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