The ’90s were when flannel was fashionable, the internet was new, and romantic comedies reigned supreme. These films were the backdrop to many a sleepover and date night, but let’s be honest: Some haven’t aged gracefully, especially regarding gender roles. Here are 14 iconic ’90s rom-coms that would face severe backlash today.

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Pretty Woman (1990)

This 1990 classic, directed by Garry Marshall and adapted from Pygmalion, follows a wealthy businessman (Richard Gere) who hires a prostitute (Julia Roberts) for a week, and they fall in love. Pretty Woman is essentially a Cinderella story with a sex work twist. Modern audiences, however, might cringe at the implications that a woman needs to be “saved” by a rich man or the way it glamorizes a highly unequal power dynamic.

10 Things I Hate About You (1999)

The plot of this 1999 classic kicks off with Cameron paying Patrick to date the feisty Kat, making her a pawn in a teenage boy’s game. The film also hinges on “taming” Kat, implying strong-willed women need to be subdued for romance. And let’s not forget the makeover scene, where Bianca’s worth skyrockets with a new look. It’s essentially Shakespeare meets high school but with more gender stereotypes than a locker room pep talk.

You’ve Got Mail (1998)

Tom Hanks charms Meg Ryan into love while simultaneously crushing her quaint bookstore under the weight of his corporate behemoth. Modern viewers might chuckle at the irony, a romantic subplot that glorifies a capitalist titan sweeping a small business owner off her feet. The film glosses over the power imbalance, presenting it as a sweet love story rather than a tale of economic conquest. Imagine rooting for the shark in Jaws because it writes cute emails.

While You Were Sleeping (1995)

In this 1995 film, Sandra Bullock’s character, Lucy, concocts an elaborate ruse, pretending to be the fiancée of a comatose man she’s only admired from afar. While sweet on the surface, this plot has some eyebrow-raising issues. Imagine the uproar today: a woman fabricating a romantic connection while her supposed partner is unconscious? It’s less “aww” and more “yikes.” This storyline dances dangerously close to gaslighting territory.

Runaway Bride (1999)

Directed by Garry Marshall, the film’s main plot focuses on Julia Robert’s Maggie, notorious for ditching grooms at the altar. This film portrays women as commitment-phobic and needing a man to fix them—enter Richard Gere, the cynical reporter turned romantic savior. The idea that Maggie’s flighty behavior stems from emotional instability, cured only by true love, is a tad outdated. Today, Maggie might be celebrated for asserting her independence rather than shamed for it.

Notting Hill (1999)

Roger Michell in, this dreamy classic, features a bookstore owner (Hugh Grant) who is swept off his feet by a Hollywood star (Julia Roberts). Problem? Sure! It glorifies the idea that a regular guy can only find happiness with a glamorous celebrity. Let’s face it: the power dynamics here are as uneven as a seesaw in an earthquake. The whole “normal guy saves famous girl from loneliness” narrative is as outdated as a flip phone.

Clueless (1995)

This contemporary retelling of Emma by Amy Heckerling showcases Cher’s matchmaking prowess as iconic, but the makeover montage raises an eyebrow or two. The film’s emphasis on appearance and the idea that a woman’s worth is tied to her looks feels as outdated as Cher’s rotary phone. Plus, let’s not forget the eyebrow-raising relationship between Cher and her stepbrother, Josh. It’s like a fashion-forward fairy tale but with a questionable moral compass. As Cher would say, “As if!”

She’s All That (1999)

The makeover trope reigns supreme in this flick. As a high school jock bets, he can turn any girl into the prom queen. This premise reduces women to mere projects, reinforcing the outdated notion that a woman’s worth is tied to her appearance. Plus, the whole plot revolves around a bet, treating the female lead like a prize to be won in a game of male competition. It’s like a wrong teen movie version of “Pygmalion” with less charm and more cringe.

My Best Friend’s Wedding (1997)

Another classic starring Julia Roberts, the Queen of nineties rom-com, showcases her scheming to break up her best friend’s wedding. Problematic gender roles emerge as Roberts’ character is portrayed as desperate and conniving in her pursuit of love. The film strengthens the stereotype of women resorting to manipulative tactics when faced with unrequited feelings rather than promoting healthy communication or gracefully accepting rejection. In today’s context, her actions are toxic and selfish rather than endearing or romantic.

There’s Something About Mary (1998)

In this comedy classic, the humor often hinges on men going to absurd lengths to win over Cameron Diaz’s character. From stalking to elaborate lies, the film portrays male entitlement as comedy gold. However, these antics seem less charming and creepier in today’s context. The relentless pursuit of Mary and the objectification of her character doesn’t quite hit the mark anymore. What was once seen as quirky and endearing now feels uncomfortably invasive, highlighting the film’s outdated portrayal of gender dynamics.

The Wedding Singer (1998)

While Adam Sandler’s crooning may charm you, the plot of this film dances around some cringe-worthy gender stereotypes. Picture this: Sandler’s Robbie epitomizes the jilted nice guy who believes he can’t move on until he finds true love. Meanwhile, Drew Barrymore’s Julia is the damsel in distress, needing rescue from a bad relationship. It’s like a dance where the steps need to be updated. Robbie leads in his quest to save Julia from her romantic woes, perpetuating that a woman’s happiness hinges solely on a man’s affection.

Never Been Kissed (1999)

In this flick by Raja Gosnell, Drew Barrymore’s character goes undercover as a high school student, romancing a teacher. Fact: The setup is as questionable as pineapple on pizza. Barrymore’s journalist character blurs ethical lines like a toddler with a coloring book. The film’s premise, akin to a midlife crisis in a teen movie, plays fast and loose with consent and professionalism. It’s like mixing ketchup with ice cream—confusing and not palatable.

Can’t Hardly Wait (1998)

Gender roles are as tangled as a ball of neon scrunchies in this rom-com. Female characters are often relegated to romantic conquests or sidekicks, while their male counterparts navigate the party scene with swagger. The film’s reliance on tired stereotypes about high school dynamics would make even the most dedicated ’90s enthusiast cringe. It’s like the movie took a time machine straight from the ’50s, bypassing any progress on gender equality.

Jerry Maguire (1996)

Ah, “Jerry Maguire,” even Tom Cruise’s big heart and Renée Zellweger’s charm couldn’t mask its gender role issues. That iconic line, “You complete me,” suggests a woman’s wholeness hinges on a man—ouch! In 1996, maybe it seemed romantic, but indeed not today. The film’s portrayal of Zellweger’s character as a single mom needing rescue backs up outdated ideas about women’s independence. In the rom-com Olympics, “Jerry Maguire” might lose points for its not-so-magical gender dynamics.