Valentine's Day Special: The Movie Couples That Don't Belong Together

We've never quite understood the appeal of going to movies for Valentine's Day. Movie-watching is, after all, a solitary activity in which a person sits in the dark staring straight ahead in silence for two hours. But people do it anyway. Perhaps that's because romance is the central activity of roughly 67 percent of movies, and people want romance on Valentine's. But Hollywood is usually terrible at matching supposedly perfect couples. The supposed happy endings of romantic comedies often feel anything but happy to us. The movies will insist the couple is supposed to be together, but we rarely think they actually should be. Today, in honor of this special day, we thought we'd take a look at two couples from beloved romantic comedies and point out that, uh, there is absolutely no way these people should be together.

Leitch

Clueless.

Clueless is so old that Julie Brown is in it, but it's still eminently quotable and holds up well enough. It's wry and self-aware, it lacks the self-seriousness of its contemporaries—no one watches this movie to mock it. (People are still talking about it more than She's All That and Empire Records, I'll say that.) It's sharp and funny and good-hearted, and clever in its Emma inspiration and its generally positive vibes. But I'm sorry: Whether no matter how true it is to literary convention or no matter how charming Paul Rudd is (as much now as 18 years ago), it's still freaking creepy that Cher ends up with her stepbrother.

The movie perhaps overplays its hand in hiding the ultimate romantic interest in plain sight. Like George Knightley in Austen's novel, Rudd's Josh is a member of the family, one who constantly and good-naturedly berates Cher. He's in college, and Cher's 16, which isn't as old as the age difference in Emma—roughly 17 years—-but is rather dramatic, particularly given how it's portrayed in the film. Josh takes on not just a brotherly role, but also a paternal one. He wants to both educate and protect her, and she looks up to him, even if she doesn't fully understand him. Which is sort of why she "falls" for him in the first place: He's so different than everyone else she knows.

This is partly because he reads Nietzsche—by the pool, of course, because who doesn't—but mostly because, well, he's so much older than she is, and obviously not a potential companion. Watching Clueless the first time back in 1995, I was stunned by the decision to put the two characters together because the movie doesn't do much to show attraction between them other than sibling-style banter. It is established, rather firmly, that they're brother and sister, all the better to throw everyone off the scent. So by the time they do get together, it feels artificial and creepy, out of place in a movie that's cheerfully the former and defiantly not the latter. I've never understood it. I like them as brother and sister. I bet, deep down, they do too. I bet they're secretly grossed out.

Grierson

Pretty Woman.

In the movies, this sort of thing seems really romantic. He's a handsome, rich ‘80s corporate raider. She's a beautiful prostitute with a sweet disposition. They've only known each other for a week, but they can't deny the love they feel. She helps him access his softer side; he gives her a life of comfort. And remember how he went to her building and climbed the fire escape to "rescue" her at the end? They're meant for one another.

Pretty Woman is, of course, a complete Hollywood fantasy, director Garry Marshall turning a script called $3,000 (a dark drama about a hooker and a businessman) into a fairy tale. There's nothing really wrong with a little bonbon gooeyness, though. The film's real problem is that it's hard to imagine that Richard Gere's Edward Lewis and Julia Roberts' Vivian Ward are going to last all that long after the final credits roll.

It's not that they're bad people. Sure, Edward is a bit of a drip, and Vivian doesn't have the best singing voice, but those are hardly deal-breakers. It's just that it doesn't matter how perfect Vivian's smile and laugh are: You just know that Edward's one of those guys who tries on a conscience for size every once in a while, likes how it makes him feel for a little bit, and then decides that being soulless is, frankly, easier. And when his buddies give him grief about it later, he'll say, "Hey, I tried. It just didn't work out."

And as for Vivian, she's gonna see through this guy eventually, right? She doesn't have his education or his privilege, but she's smart. Expose her to a little culture—she gets all weepy over La Traviata, after all—and soon she'll realize that Edward is just another boring suit who can't appreciate the finer things in life. (Also, he's 18 years older than her.) Yes, his money will sure be nice at the start, but she'll get tired of it—and him— pretty soon.

It's easy to see why lots of women I know love Pretty Woman. It tells audiences that your Prince Charming will come to save you but, in a tip of the hat to modern-day feminism, that the woman will save him right back. But in real life, I'm not convinced these kinds of guys really want to be saved. They just want possessions, whether they be down-on-their-luck corporations or beautiful arm candy. The sad truth is, somebody like Edward will do his best to be a good guy to Vivian for a while. But eventually, he's probably going to trade her in for a younger model. Plus, you just know he's one of those bastards who got rich in the subprime mortgage scandal. Ladies, you're better off without this guy, even if he does look like Richard Gere.

Grierson & Leitch is a regular column about the movies. Follow us on Twitter, @griersonleitch.