Top 10 Rom-Coms Moments That Haven't Aged Well

Granted, the intentions of “date doctor” Hitch Hitchens aren’t all bad. He wants to help men who struggle to date find love in long-term relationships. But he still teaches men to use manipulative tactics to make an impression. He also assumes that he knows all about what women want, even when it’s in conflict with what women actually say. It turns out, what he thinks women want is often completely wrong. Of course, by the end of the movie Hitch learns his lesson. But his character is so problematic that we can’t imagine him being the focus of a movie today.

In this 2009 romantic comedy, two best friends, played by Kate Hudson and Anne Hathaway, become sworn enemies when their weddings are scheduled for the same day at the same venue. So they decide to sabotage each other’s special day. It’s a premise that perpetuates the stereotype that female friendships are plagued by jealousy and backstabbing. Why didn't they just have a double wedding? All the pranks they pull on each other are supposed to be funny, but when you look at them through today’s lens, they’re really just pathetic. Even though they make up in the end, it sends a pretty destructive message to viewers.

The intention of this movie was to show that beauty is only skin deep, but the delivery is very dubious. After being hypnotized by motivational speaker Tony Robbins, Jack Black’s character Hal is forced to see people's inner beauty as their outer beauty. It’s an interesting premise, but there’s still a lot of superficiality and body shaming on the way. Jason Alexander’s character Mauricio is particularly mean-spirited and judgemental. Neither Hal nor Mauricio fit stereotypical standards of male beauty, yet they see women who they deem unattractive as worthless. Again, they learn their lessons, but it’s cringey to watch them get there.

Adam Sandler’s Danny uses a cheap trick to pick-up women: he pretends to be unhappily married, then sleeps with them without the “risk” of commitment. In other words, he lies to get women into bed. When he actually falls for a woman, Brooklyn Decker’s Palmer, this gets him into a world of trouble. She discovers his fake ring, and rather than reveal what he’s used it for in the past, he gets his employee and friend Katherine to pose as his wife. It goes without saying, lying to someone to sleep with them, or to pursue a romantic relationship with them, is hella wrong. It isn’t just a flaw, it’s a huge red flag.

Rewatching this movie today, it’s difficult to find anything redeemable about male chauvinist Mike Chadway, played by Gerard Butler. Sure, Katherine Heigl’s Abby has some quirks, such as a commitment to questionable self-help books and an idealistic view of relationships. But Mike is a conceited pig who reduces women to objects and dishes out his own sexist assumptions about the opposite sex as gospel. How do these two even end up together? This kind of all knowing male trope is an infamous flaw of rom-coms that we’ve been victim to ever since Harry met Sally.

This Kevin Smith film follows Ben Affleck’s Holden as he chases after Alyssa, even though he knows she’s a lesbian. Or at least, she is, until Holden comes along. This perpatuates the idea that being gay is a simple matter of choice, like having a switch that can just be turned on or off. To make it worse, when Holden finds out that he isn’t the first man she’s slept with, he’s angry with her and expects her to feel ashamed. In fact, he ends up dumping her for it … then regretting it and asking her to have a threesome. Yeah, it’s honestly pretty baffling. Talk about entitlement.

This could be seen as another case of good intentions gone wrong. Chuck and Larry pretend to be gay so that Larry can name his kids as beneficiaries in his life insurance. On one hand, the characters learn lessons about how it feels to face discrimination, and generally change for the better. On the other, it’s a story about a supposedly gay couple without real gay representation. And the way it does represent gay couples is rooted in stereotypes. Not to mention there's also that scene where Chuck feels up his lawyer while still posing as gay.

This one is so wrong, it’s hard to understand how it was well-received at the time. Isla Fisher’s character Gloria becomes obsessed with Vince Vaughn’s Jeremy and relentlessly pursues him no matter how many times he tells her to back off. One night she surprises him while he’s asleep, ties him down, and assaults him. This traumatic event is somehow written off as a big joke. In 2006 this movie even made Premiere Magazine’s list for “The 50 Greatest Comedies of All Time”. Such predatory behavior should never have been treated as something to laugh at.

Get ready for yet another “how did anyone ever think this was OK” moment. When Jake’s girlfriend Caroline passes out at a party, he notes idly that he could “violate her” if he felt like it. But he’s just not into her anymore. So he passes her off to Ted ... How is THIS the movie’s romantic lead and supposed heartthrob?! As Ted and Caroline are about to drive off, Jake convinces an inebriated Caroline that Ted is in fact Jake, and tells Ted to “have fun”. Ted takes full advantage, and the next day Caroline is portrayed as pretty much fine with it all. Talk about wrong … as well as completely delusional.

Based on Truman Capote's 1958 novella, “Breakfast at Tiffany’s” remains a beloved classic. But sadly, it’s not all kissing in the rain and “Moon River”. There’s one aspect of the film that many would love to forget. Audrey Hepburn’s Holly Golightly has a Japanese landlord, Mr. Yunioshi, who’s inexplicably played by Caucasian actor Mickey Rooney. Even decades later, this continues to be talked about as one of the most offensive instances of yellow face in cinema history. Mr. Yunioshi is a caricature whose ethnic identity is played purely for laughs. While whitewashing continues to be a problem in Hollywood, we’ll hopefully never see another instance quite as awful as this.