That Didn’t Age Well: 20 Rom-Com Movies That Are Problematic Today

All About Steve (2009)

It’s one thing to play quirky. It’s another to portray stalking behavior as charming and romantic. All About Steve tries to do both – and the result is more unsettling than sweet. Sandra Bullock plays a crossword puzzle creator who becomes obsessed with a news cameraman and follows him across the country, convinced they’re meant to be together. What’s framed as cute persistence actually reads like an unhinged lack of boundaries. While it aims for offbeat charm, the film inadvertently makes light of mental health and consent. Not exactly the feel-good rom-com energy we’re looking for in today’s world. | © 20th Century Fox

Hitch (2005)

The premise of Hitch feels innocent enough: a "date doctor" helps awkward guys win over women who seem out of their league. But peel back the charming Will Smith exterior and you'll find some pretty sticky gender dynamics. The entire setup hinges on manipulating behavior to win affection – using tricks, tactics, and rehearsed moves instead of, you know, actual communication. It also leans into outdated stereotypes about women being emotionally unpredictable or in need of decoding. And let’s not forget the glaring lack of LGBTQ+ representation in a film about dating “science.” What passed as smooth in the 2000s now comes off as a bit manipulative. | © Columbia Pictures

Wedding Crashers (2005)

Let’s be honest – this one was already controversial when it came out. Two guys make a sport out of lying their way into weddings to hook up with women. In today’s climate, that’s less "romantic mischief" and more a textbook case of deception and manipulation. Wedding Crashers gets especially dicey with scenes that blur lines of consent, particularly when played for laughs. There’s also some uncomfortable handling of LGBTQ+ characters and outdated jokes that wouldn’t land today. Sure, it's packed with charisma and comedy, but its foundational premise raises some real ethical red flags. | © New Line Cinema

13 Going on 30 (2004)

This one is bittersweet because it’s still a favorite for many. But through a modern lens, 13 Going on 30 has some iffy plot points that can’t be ignored. The body-swap age-gap dynamic – where a 13-year-old girl magically wakes up in her 30-year-old body – raises major questions when it comes to romantic interactions. What’s intended to be adorable gets a little murky once you realize the character is still emotionally a teen navigating adult relationships. While the movie nails nostalgia and heart, it fumbles when it asks viewers to ignore some pretty questionable implications. | © Columbia Pictures

Love Actually (2003)

It’s considered a holiday staple, but Love Actually is a minefield of problematic tropes when viewed today. From the fat-shaming jokes aimed at Natalie to the romanticizing of a man who silently obsesses over his best friend’s wife (and then shows up with cue cards), the movie sends some seriously mixed messages about love. There’s also the weird imbalance in workplace dynamics and the idea that grand gestures should override emotional boundaries. For a film that tries to explore “love in all its forms,” it forgets to include any healthy communication – or basic respect, in some cases. | © Universal Pictures

Bridget Jones’s Diary (2001)

Ah, the beloved tale of a single woman navigating love, work, and her ever-changing weight. While Bridget Jones’s Diary charmed millions with its relatable messiness, it’s hard to overlook how deeply it leans into body-shaming and outdated ideas about what makes a woman “desirable.” Bridget is constantly ridiculed – by herself and others – for being what’s now considered average size, and the film plays her self-loathing for laughs. Add in the boss-employee romance with some serious HR red flags, and you've got a rom-com that would face a much tougher crowd if released today. | © Universal Pictures

The Wedding Planner (2001)

If your fiancé falls in love with the wedding planner, it’s probably not the start of a fairy tale – it’s a red flag. The Wedding Planner plays infidelity like it’s just a quirky obstacle on the path to true love. The film frames Matthew McConaughey’s emotionally unavailable character as swoon-worthy, while Jennifer Lopez’s character basically gets rewarded for being the "other woman" without any real consequences. Throw in the classic rom-com trope of Italian stereotypes and a near-marriage based on family pressure, and it all starts to feel more awkward than romantic. | © Columbia Pictures

Never Been Kissed (1999)

High school is already weird, but when a 25-year-old reporter goes undercover as a student and starts flirting with her teacher – who doesn't know she’s an adult – it veers into downright uncomfortable territory. Never Been Kissed wants us to root for a romance that hinges on a massive ethical gray area. Even though the intentions are innocent, the power dynamics and student-teacher setup feel way off by today’s standards. Add in the mocking of nerdy kids and some outdated views on popularity, and it’s easy to see why this one doesn’t quite hold up. | © 20th Century Fox

Cruel Intentions (1999)

Stylish, seductive… and wildly problematic. Cruel Intentions took the scandals of Dangerous Liaisons and dropped them into a preppy teen setting, but it didn’t leave the manipulation behind. The entire premise is based on deceit, coercion, and sexual wagers, with characters using others as pawns in twisted social games. There’s even a literal bet over taking a girl’s virginity. The film tries to frame this as darkly romantic, but watching it now, it’s less hot and more deeply uncomfortable – especially considering it was marketed to teens. | © Columbia Pictures

She’s All That (1999)

Turning a bet into a love story might have flown in the ’90s, but today, it raises more than a few eyebrows. In She’s All That, a popular jock wagers he can transform a “nerdy” girl into prom queen – because apparently glasses and overalls are the height of hideousness. The makeover trope here is less about self-confidence and more about fitting into a narrow idea of what makes someone attractive. It also subtly reinforces the idea that women need to change in order to be loved, and that’s a message that’s aged about as well as frosted tips. | © Miramax Films

Addicted to Love (1997)

Romance and revenge don't usually go hand in hand – unless you're in Addicted to Love, where stalking, spying, and psychological sabotage are all played for laughs. The film follows two jilted lovers who team up to destroy their exes’ new relationship, setting up surveillance, rigging sabotage, and basically acting like cartoon villains. Somehow, it’s all meant to lead to a love story? Yeah, no. Today, this kind of behavior would land you in jail or at least on a watchlist, not in a quirky romantic montage. | © Warner Bros. Pictures

While You Were Sleeping (1995)

Yes, it’s cozy. Yes, Sandra Bullock is charming. But While You Were Sleeping asks us to root for a woman who pretends to be engaged to a man in a coma... and then falls for his brother while keeping up the lie. It's peak ‘90s rom-com absurdity, but the deception at the heart of the plot makes it hard to cheer for the romance without squinting a bit. In today’s storytelling climate, the idea of building a relationship on that kind of lie might feel less "aww" and more "ugh, that’s weird." | © Walt Disney Studios

Clueless (1995)

Don’t get us wrong – Clueless is still a cultural reset. But if we’re being honest, there are a few aspects that would raise eyebrows today. Cher's well-meaning but wildly manipulative matchmaking efforts (especially with her teachers and friends) show a total lack of boundaries. And let’s not forget the fact that her eventual love interest is her former stepbrother – played as perfectly normal, even romantic. While the fashion and quotable lines are timeless, some of the relationship dynamics haven’t exactly aged like a fine Alaïa. | © Paramount Pictures

Sleepless in Seattle (1993)

It’s one of the most iconic rom-coms ever, but Sleepless in Seattle takes a big swing on the idea of fate – and skims a little too close to obsession. Meg Ryan’s character essentially hears a stranger on the radio and becomes so emotionally invested in his story that she flies across the country to pursue him… without ever meeting him. While framed as romantic destiny, the lack of consent, boundaries, or, you know, normal communication, might feel a little invasive today. Sweet? Sure. But also a little stalker-adjacent. | © TriStar Pictures

Chances Are (1989)

Reincarnation rom-coms are already a tricky sell, but Chances Are really takes things to a weird place. The film follows a man who’s reincarnated into the body of a college student and realizes he’s the husband of his friend’s mom – who he’s now romantically interested in. There’s a lot of emotional whiplash and very little concern for, well, basic boundaries. It’s framed as a whimsical love story with a supernatural twist, but today it reads more like a Freudian fever dream. | © TriStar Pictures

Big (1988)

A boy makes a wish to be “big” and wakes up as a full-grown man – sounds innocent enough. But Big takes a hard left when a romantic relationship develops between this now-adult-bodied child and a grown woman who has no idea he's actually 12. Sure, Tom Hanks plays it with charm, and the film is still beloved, but the whole plot revolves around a situation that, if reversed, would be completely unacceptable. Today, the idea of romanticizing a child in an adult’s body raises major ethical red flags. | © 20th Century Fox

The Breakfast Club (1985)

A teen classic, yes – but The Breakfast Club comes with a generous helping of '80s-era baggage. The film explores adolescent stereotypes with surprising depth, but it also includes bullying, slut-shaming, and a “romantic” subplot where one character literally harasses another into falling for him. Add in a makeover that implies a girl is only attractive once she conforms, and you've got themes that haven’t exactly aged gracefully. We still love the soundtrack – but the social dynamics are a lot messier in hindsight. | © Universal Pictures

Sixteen Candles (1984)

It’s one of the most referenced teen rom-coms of all time – and also one of the most uncomfortable to rewatch. Sixteen Candles is filled with casual racism (yes, we’re looking at you, Long Duk Dong), deeply troubling consent issues, and the classic ‘80s obsession with underage drinking and voyeurism. A guy giving away his passed-out girlfriend like she’s a party favor? Played for laughs. It’s a film frozen in time – and that time didn’t think much about accountability or cultural sensitivity. | © Universal Pictures

Blame It on Rio (1984)

This one is, frankly, a full-on cringe-fest by today’s standards. Blame It on Rio centers around a grown man having an affair with his best friend’s teenage daughter while they're all on vacation together. It’s framed as awkward and comedic, but the reality is that it’s predatory and deeply inappropriate. The entire movie operates under the outdated assumption that this kind of dynamic can be “complicated” rather than outright exploitative. Even in the ‘80s, this one raised eyebrows – today, it’s almost unwatchable. | © 20th Century Fox

Endless Love (1981)

Nothing says “problematic romance” like obsession, arson, and emotional manipulation. Endless Love takes a wildly unhealthy relationship and tries to pass it off as epic teen passion. The male lead becomes dangerously fixated on his ex, even committing crimes to stay close to her, and the film still frames it as tragic love rather than a glaring mental health crisis. Add in the parental dynamics that range from enabling to disturbing, and you've got a story that would trigger serious content warnings today. | © Universal Pictures