10 Problematic Rom-Coms That I’d Never Let My Tween Daughter Watch

The romantic comedy is a beloved genre that has proven itself to be exceedingly popular, be it at the box office or a girl’s night viewing party. I, too, once enjoyed the light-hearted and romantic charm of many movies on the following list. But now that I’m a mother to a tween daughter who’s getting all kinds of bad messaging from the world of media and entertainment, I realized that many classic rom-coms need to be seriously reevaluated. Without further ado, here’s my roundup of very problematic rom-coms that I’d never let my daughter watch.

• Director: Raja Gosnell
• Cast: Drew Barrymore, Michael Vartan, David Arquette, James Franco, Jessica Alba

The plot of this really icky rom-com involves a journalist, Josie Geller, posing as a high school student in order to investigate teen culture. The movie takes a turn for the worse when Geller (who is not actually 17) falls for her attractive high school English teacher (who definitely thinks she’s 17). Here’s the kicker: the attraction is mutual. Needless to say, a budding romance between an adult teacher and an adult pretending, quite convincingly, to be a juvenile has major pedo vibes and is quite problematic. Love you, Drew Barrymore, but this is definitely not your best look.

• Director: Donald Petrie
• Cast: Kate Hudson, Matthew McConaughey, Kathryn Hahn, Adam Goldberg

Nothing tugs at one’s heartstrings quite like watching two pretty crappy people fall in love as a result of their pretty crappy behavior. If you agree, watch this charmer from the early 2000s about a woman on a mission to prove she can repel any lovestruck dude in 10 days and a man who wants to win a bet that he can make any woman fall in love with him in the same timeframe. The entire premise of their (you guessed it, weirdly successful) romance is cringy manipulation and ulterior motive. What’s most exciting is that there are actually rumors of a sequel! Let’s just hope it includes an honest portrayal of how marriages end up when two people treat each other like pawns.

• Director: Gil Junger
• Cast: Julia Stiles, Heath Ledger, Joseph Gordon-Levitt, Larisa Oleynik

I could list more than 10 things I hate about this movie (and why my tween daughter won’t be watching it) but that would fill a page. The tldr? 10 Things I Hate About You is a modernized version of The Taming of the Shrew. For those not familiar with the Shakespearean play, it involves a smart and independent woman, a suitor who wants to tame her into being a submissive wife, a controlling father and a younger sister who isn’t allowed to marry until her older sister (i.e., the shrew) does. Now, take that Shakespearean plot line and turn it into a sugar-coated teen rom-com that completely glazes over all the problematic gender roles and inherent sexism in the story. Ta-da!

• Director: Richard Curtis
• Cast: Hugh Grant, Emma Thompson, Colin Firth, Keira Knightley, Liam Neeson, Bill Nighy

Ahh, yes, the Christmastime classic that leaves everyone atwitter with feelings of love…but only if you’re able to overlook the numerous questionable messages served up in this movie featuring nine intertwined love stories. (Hint: all of them are toxic.) I know this one is a favorite of many romantics, so I hate to be the bearer of bad news but it hasn’t aged well. There’s the near-constant fat shaming of one character (Natalie), the fact that none of the women seem to have any agency in their romantic relationships, plus an overall commitment to using corny tropes as a tool to make sexism look cute. Please, friends, don’t teach your daughters that this is love, actually.

• Director: Jon Turteltaub
• Cast: Sandra Bullock, Bill Pullman, Peter Gallagher, Peter Boyle

I love Sandra Bullock (who doesn’t?!), but oof! In this bizarre and straight-up disturbing rom-com from the mid 90s, the romance centers around a female subway worker who has the hots for a handsome commuter. She finds herself in a position to save his life, later visits him in the hospital where he’s in a coma and then (wait for it) lies to all his family members about being his fiancee. In other words, it’s more like Fatal Attraction…but cute. I would never, ever show my daughter this movie—and if you don’t get the problem with it, I have one word for you: consent.

• Director: Peter Segal
• Cast: Drew Barrymore, Adam Sandler, Rob Schneider, Peter Segal

While You Were Sleeping was a real trailblazer; in fact, it paved the way for another abomination called 50 First Dates. Here, a commitment-phobic man with a penchant for lying to women believes he has met the one of his dreams, an art teacher who suffers from a serious neurological condition called anterograde amnesia. They have one fun afternoon and then she can’t remember him the next morning, but he persists—recreating that “first date.” There are serious issues of consent, manipulation, deceit and, I don’t know, the fact that a man is using a neurologically impaired woman for his own romantic gain. Oh, and there’s something not-so-funny about using a serious health condition as fodder for laughs in a rom-com. Need I say more?

• Director: Nora Ephron
• Cast: Meg Ryan, Tom Hanks, Ross Malinger, Rita Wilson, Bill Pullman, Rosie O’Donnell

At this point, I’m starting to feel a little guilty about ripping apart 90s staples from the genre. Alas, when you rewatch these films through a different lens, it’s hard to deny that they’re all pretty problematic. Sadly, Sleepless in Seattle is no exception—namely because it involves a woman (Meg Ryan) basically stalking a man (Tom Hanks) that she’s never even met and has only heard on the radio. In order to have the in-person meeting she so desires, she uses her professional credentials and resources as a journalist to lie her way into getting information on him so she can hunt him down and stage a serendipitous encounter. It’s beyond creepy, highly unethical and, unsurprisingly, the ensuing romance is just as far-fetched as the orchestrated initial encounter.

• Director: Robert Iscove
• Cast: Rachael Leigh Cook, Freddie Prinze Jr., Matthew Lillard, Paul Walker, Anna Paquin

Here, a seemingly innocuous if not completely unoriginal storyline that shows an exaggerated version of teen social dynamics. The outcast gets a makeover after some popular guy makes a bet that he can turn her into prom queen—a tired ugly duckling turns into swan plot that sends the completely wrong message to girls about what they should be valued for. (Not to mention the fact that women should never unwittingly be involved in other people’s bets.) Beyond that, there’s lots of bullying, shallow relationships that aren’t believable and every other objectionable thing you can think of in this rom-com. If you want a more thorough takedown, you can read it here.

• Director: P.J. Hogan
• Cast: Julia Roberts, Dermot Mulroney, Cameron Diaz, Rupert Everett, Carrie Preston, Christopher Masterson

Julia Roberts is one of Hollywood’s most likable actresses. Alas, the same cannot be said for her character in this classic and deeply troubling rom-com from the 90s—namely because the entire movie revolves around her manipulating and plotting to break up another couple. The story goes like this: Julianne Potter wants to prevent her childhood best friend, Michael O’Neill from getting married in order to force him to follow through on a deal they made to marry each other if they were single by the time they reach the ripe old age of 28. Julianne Potter is what one might call a terrible person, but her best friend and love interest is not exactly what you’d call a catch either. (You can read more about that here.) Bottom line: if you want to see what toxic narcissism looks like when it tries love on for size, watch this movie.

• Director: Garry Marshall
• Cast: Julia Roberts, Richard Gere, Laura San Giacomo, Hector Elizando, Jason Alexander

Sorry, Julia, but I’m coming for you again because Pretty Woman is pretty problematic. This rags-to-riches romance about a beautiful sex worker who essentially becomes the adoptive girlfriend of a businessman who earns his living by destroying companies is wrong on so many levels. For starters, it makes prostitution look glamorous and suggests that true romance can come from transactional sex rather than genuine intimacy. Then there’s also the problem with how Julia Roberts’ character is treated throughout the movie. If Richard Gere’s character is actually her prince charming, why does it still feel like she’s been reduced to a sex object that’s passed around? File this one under sexism and the patriarchy.