It’s impossible to look back on cinema as a whole and not come up with a slew of popular-yet-problematic offerings, and the romantic comedy genre’s no exception. From Mickey Rooney’s diabolically racist character in Breakfast at Tiffany’s (1961) to the questionable prospect of a man falling in love with a woman with a child’s mind in 13 Going on 30 (2004), there’s a deep well of “yikes” material from which to draw.

Still, while some of these problematic cinema sins are unforgivable or a sad product of their time, some rom-coms are still relevant even now. These romantic comedies may be problematic, but they deserve a closer look. Are they problematic only now, or were they instead purposely shining a lot on the very thing they’re now criticized for? Or maybe the things that make them questionable aren’t as bad as they seem on the surface? Let’s do a deep-dive.

Will you forgive these movies and watch them anyway, or relegate them to the rom-com graveyard?

Clueless (1995)

We’re starting with a light one here. Even at the time, viewers were at odds not with the movie, but with themselves. While you can talk about the problematic nature of making over your friends to be just like you, or tricking your teachers into falling in love, the real sin of Clueless is the, well, incest.

Of course, “incest” is a big word. Yes, Cher and Josh are siblings, but the relationship needs a lot of qualifiers. First, they’re step-siblings. Second, their parents were only married for a short time and had divorced years prior to the start of the film. They’re only step-siblings by a technicality.

This weird familial relationship to the movie’s main romantic couple is a smoke-screen for something with a bit more of an ick to it. While the sibling relationship was a hot-button topic at the time, age-gaps weren’t as much of a problem. Take the movie Sleepover from 2004. The main girl was a literal middle schooler and she ends up with a high school senior in the end, and no one said anything at the time. It’s only in 2023 that people are starting to wise up to how predatory these age gaps are.

In Clueless, Cher is supposed to be 15. (Yes, 15!) And Josh is not only in college, but he’s several years into it. Let’s say he’s 19 just to be generous (but he’s more likely 21.) That’s the biggest yikes of this whole movie. But do we all collectively forgive Clueless? Of course. Because no matter what their relationship or the gap in age, it’s Paul Rudd. And that man can do no wrong.

While You Were Sleeping (1995)

Lucy (Sandra Bullock) has a huge crush on the bushy-eyebrowed guy she sees on the subway while she’s taking people’s tokens. We’ve all been there, crushing hard on a stranger we’ve never spoken to. We’ll invent all manner of ways we meet and fall in love. It makes those boring train journeys–or classes, or work–so much more interesting. Crushes aren’t the problem here, though. It’s what she does with that crush after he ends up in a coma.

Her obsession with this man she’s never actually spoken to draws her to the hospital to see if he’s okay…and she runs right into his family. Rather than being like, “Oops, I’m in the wrong room,” Lucy instead pretends to be in a relationship with the man. Yikes. And so snowballs a whole scenario where she’s invited to family get togethers and lies about how they met and what they are to each other. And, even worse, she ends up falling for his brother. Because of course a relationship built on spectacular lies is going to end up okay.

Unlike the other movies on this list, being upset with the problematic nature of this movie was more relevant at the time than it is now. At the time, morally gray characters just weren’t a thing in romantic comedies. While the indie romance genre features plenty of unsatisfying endings in recent years, all we had back in the ’90s was sugary love and guaranteed happy endings. And while Lucy and Jack’s ending was certainly painted as happy, the stalker-centric deceit felt icky to a lot of viewers at the time.

Now though, While You Were Sleeping can be appreciated right alongside the other romance movies of today that feature deeply flawed characters falling in love despite their questionable personalities. Lucy wasn’t a good person, but even icky people find love. It was a rom-com out of time, fitting in now more than it ever could in the cookie-cutter romantic comedy landscape of the 1990s.

Shallow Hal (2001)

You’ve likely heard of this movie, even if you haven’t seen it. Regularly popping up in TikToks about movies that “couldn’t have been made today,” Shallow Hal is about, well, a shallow man named Hal. Although he’s played by the loveable Jack Black, he’s truly detestable. All he cares about is looks–personality has no baring when it comes to both who he wants to sleep with and even who he wants to befriend.

The main reason why this movie keeps getting brought up today is because of the perceived fat-shaming in the movie. Gwyneth Paltrow even dons a fatsuit, showing that fat women are never loved when their looks are taken into account. Here’s the thing though: For the people saying “this couldn’t be made now,” the movie could barely be made back in 2001.

It’s not like Shallow Hal was celebrated in its time. All the complaints you’re hearing about the movie have all been said even before it came out. The fat jokes abound, and people weren’t having it in 2001.

While there certainly are problematic things about this movie (namely the intense depression and disordered eating that Paltrow’s fat double went through after the show), it isn’t as reprehensible as it sounds. The moral of the story is not to judge a book by its cover. Hal is shallow precisely because he’s a fat-shamer. The audience is made to hate Hal, and not his fat counterpart. The only thing that could modernize the film is ditching the idea of “she’s hot despite her fatness” and instead replacing it with, “She’s fat, and she’s hot, and these things aren’t mutually exclusive.”