5 Classic Romantic Comedies That Teach Questionable Lessons

No movie genre ages quite like the romantic comedy. While most films are dated by laughable special effects or ancient references, older rom-coms tend to spit in the face of everything that we consider socially acceptable. They're usually a parade of creepy gestures, misguided attraction, and outright workplace harassment -- all of which was apparently considered charming and adorable at the time. Just look at how ...

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5
Two Week's Notice Is About Truly Awful Boss/Employee Power Dynamics

In Two Week's Notice, Hugh Grant plays an especially Hugh Grant-ish character: a real estate mogul with a penchant for hiring attractive women with bullshit law degrees to be his chief legal council. He then fucks them and fires them once he "realizes" they aren't qualified. This was apparently considered an endearing personality flaw in 2002.

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Enter Sandra Bullock, a Harvard grad who is absurdly obsessed with her local YMCA. Hugh offers her a job in exchange for promising to protect her beloved community center from his wrecking ball's wrath. This, it turns out, involves helping him pick out a mattress, select the right tie, choose the best monogrammed envelopes, and even chat up his dates at 3 a.m. for no apparent reason. Sandra becomes his nanny/mother, which the film implies is a legitimate, if imperfect, foundation for a romance. This wealthy, clueless manchild is lost without a wise woman in his life! What girl wouldn't want to swoop in and spend her life cleaning up for him?

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Sure, at one point, Sandra's character gets fed up and gives her two week's notice (that's the title of the movie!!), to which Hugh responds reasonably by telling all of the local legal firms to not hire her. It's an "If I can't have you, no one else can" deal, and he manages to somehow make it grosser when he agrees to let her go as long as she finds a qualified (read: HOT, FEMALE) lawyer to replace her.

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After Hugh eye-fucks and approves of her choice, he's playing strip poker with the new girl in no time, and Sandra's reaction is ... jealousy? Yep, she's not angry about Hugh continuing to use his position to get sex from employees, but because he's not playing strip poker with her. Watching him hit on the new baby-faced lawyer makes Sandra realize she wants what every chief legal council apparently wants: to screw her creepy boss.

Aside from a heartwarming scene wherein Hugh Grant suggests that Sandra take a shit in his BMW during rush hour, this movie is a pre-#metoo fever dream. It tells us that sexual harassment is to be expected -- nay, desired -- and that the immature weirdo who makes you perform unpaid emotional labor at 1 in the morning is actually your true love.

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Related: 15 Movie Romances That Are Actually Creepy As Hell

4
Shallow Hal Tells Us It's Wrong To Discriminate Against Fat Women, And Also Fat Women Are Hilarious Monsters

Shallow Hal stars Jack Black as the titular Hal who is shallow, a man who only goes for supermodels because of his father's deathbed wish for him to marry a hottie. (Side note: Most romantic comedy premises are deeply strange in retrospect.) Hal meets a beaming Tony Robbins, who voodoos him into only seeing people's inner beauty -- specifically by making inner beauty manifest as outer beauty.

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This is played as if it's boldly progressive, but the central joke is Hal attempting to woo and flirt with "ugly" women as if they were hot. Get it? He's being nice to them because he thinks they're pretty, but they're not. Who says that writers of gross-out comedies can't also teach us to be better people?

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The movie bravely critiques a culture that mocks any body that doesn't fit into an insanely narrow definition of beauty by itself mocking any body that doesn't fit into an insanely narrow definition of beauty. Fat women are always the punchline, with the movie reveling in all the broken chairs and cankle jokes that entails. Gwyneth Paltrow also dons a fat suit (when portraying how she "really" looks) to teach us a lesson about open-mindedness by pointing out how hilarious it would be if she looked like that. Also she eats half of a birthday cake in one bite, because fat people, am I right?

And so we're supposed to feel great about ourselves for rooting for Hal when he eventually deigns to see Paltrow as attractive despite her fat suit. His shallowness is cured, and the audience gets to laugh at plenty of jokes about big butts, because every bit hangs on the assumption that the audience is just as shallow as Hal, only without the desire to change. It's almost like the movie wants to moralize about stereotypes while simultaneously cashing in on them. And isn't that the true magic of Hollywood?

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Related: 5 Romantic Comedy Gestures That Would Get You Slapped

3
In She's All That, A Woman Just Needs A Man To Unlock Her True Beauty

She's All That starts out by having an appropriately smug Freddie Prinze Jr. get dumped by his girlfriend. He then boasts to his friends that he could transform any girl into his ex, and get her crowned prom queen to boot. After all, Freddie implicitly argues, women are chock-full of potential; all they need is to be molded by the style-savvy star of Scooby-Doo 2: Monsters Unleashed.

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If this premise sounds familiar, that's because it is! Indeed, She's All That is an adaptation of the famous George Bernard Shaw play Pygmalion, which was itself a spin on an ancient Greek myth about a sculptor who falls in love with a bangin' statue that he carved himself. Of course, that statue came to life, but there's enough wiggle room to reasonably discern that he totally fucked it before then.

Anyway, ready to carry on the hallowed tradition of men treating women as literal lumps of clay, Freddie sets out to implement an unsolicited self-improvement regimen upon one lucky gal. His jock friends select gross nerd Rachael Leigh Cook, which in Hollywood means she's a perfect 10 who wears glasses and likes art.

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Despite her best instincts, Rachael lets this douche into her world of paint-splattered shoes and actually caring about shit like the Rwandan genocide. Freddie reciprocates by taking her to the beach with his atrocious friends and siccing his makeover-happy sister on her. With a few swift plucks of the tweezers, Rachael transforms into someone who just might be hot enough to win the approval of her student body. Dreams really do come true!

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Rachael learns of Freddie's schemes and dumps him, but of course, this genre can't allow the credits to roll there. Instead, Freddie's worst friend woos her and tries some non-consensual stuff on prom night. Compared to an unsuccessful rapist, Freddie suddenly seems like a prince, and when he shows up at her door later, she happily kisses him. Note that she's still fully in her post-makeover form here, and remains that way through the end.

But that's OK, because the guy also changed, in that he allowed himself to be attracted to an incredibly hot nerd whom he had modified to suit his own tastes.

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Related: 5 Romantic Comedy Tropes That Would Be Creepy In Real Life

2
In There's Something About Mary, Your Stalker Might Be The One!

There's Something About Mary is, like Shallow Hall, a Farrelly Brothers movie from the mid '90s, which means it was destined to age about as well as the Black Plague.

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The films centers around Mary, a perfectly nice young woman who happens to be so hot that she drives every man she meets into temporary insanity. But despite some attempts to give her a personality-lite (She likes Harold & Maude! She has a job! She's, um, nice to others!), she's mostly free-spirited eye candy. The real emotional journey belongs to Ben Stiller's Ted, who famously zips up his junk on prom night, squandering his teenage hopes of some backseat finger-blasting before college.

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Thirteen years later, Ted is still not over Mary, even though he hasn't seen her since his genital trauma. Ted sees this as a sign that his love is pure and not just the outgrowth of an unresolved issue surrounding his teenage sexuality. So he hires a private detective to find/stalk Mary. You know, like the villain of a movie would.

The detective immediately falls under Mary's spell, and before you know it, four different men of varying levels of sanity and emotional health are straight-up brawling over this lady. They demand to know which man she's into, because they clearly deem her incapable of dating around like a normal person. Eventually, the highly obedient Mary chooses Ted, because in the end, it turns out the obsessive stalker was right. They were meant to be together, and it was just a matter of the target coming around to the truth! Which, now that I think of it, brings to mind an oddly similar example ...

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Related: 6 Romantic Movie Gestures That Can Get You Prison Time

1
Sleepless In Seattle Is About Being Stalked Into A Relationship

Sleepless In Seattle is a Nora Ephron classic that brilliantly argues that your truest love is the person flying across the country to spy on you based on "gut instinct." It stars Meg Ryan and Tom Hanks, the actor equivalents of warm cookies and a glass of milk. Which makes it a prime example of how the right cast can smooth over even the most unsettling of plots.

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Hanks plays a hot widow whose eight-year-old son calls an advice radio talk show in hopes of finding his dad someone new. You know, the way kids do. Hanks talks to the radio host, and women everywhere swoon, but none so much as Meg Ryan, a journalist who writes him a love letter. In 2019, anonymously receiving a letter from a radio show listener usually means you've been doxxed by QAnon, but apparently this was still heartwarming in 1993.

As with any rom-com, both Meg and Tom have those "Plan B" partners whom we're supposed to hate. Except Sleepless In Seattle forgot that "supposed to hate" part, as Meg's boyfriend just has chronic allergies and Tom's girlfriend doesn't like camping. Those are two really reasonable human attributes to have, but the movie treats them as debilitating flaws that you dump someone over as soon as, and I can't stress this enough, you decide to pursue a complete stranger whom you briefly heard on a radio show.

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After receiving a response from Hanks' third-grade son and, against all odds, believing that it's from Hanks himself, Meg flies out to Seattle to ... stare passionately at him? In one demonstrative moment, Meg watches from afar as father and son frolic on the beach. If you're thinking that minor changes in editing and score would turn this into a horror movie, someone already proved that years ago:

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Ultimately, the three members of this star-crossed family unit meet atop the Empire State Building, and you just kind of assume that Tom Hanks lives happily ever after with a woman who stalked him based on virtually zero actual information. If there was a Sleepless In Seattle 2, it would just be Tom and Meg screaming over mortgage payments, because god forbid they get to know each other outside of disembodied radio voices and letters from grade-schoolers.

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For more, check out Why Romantic Comedies Are Secretly Bad For You - After Hours:

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