It's easy to see why this would happen. Many screenwriters who choose to write about high school didn't have a magical four years there and most screenwriters are male. So of course when they write a screenplay about high school, it's going to center around the nerdy guy they feel they were. And in their movie, they are going to get the girl.
But will it be their best girl friend? No. Will it be the girl who loves the bands they love? No. Will it be the most popular girl in school? Of course.
Now if the most popular girl in school actually has the hots for the nerdy guy, I don't blame her. But what I can't ever seem to understand is why in the majority of movies about high school (Can't Hardly Wait, Pretty In Pink, The Breakfast Club, etc.), the nerd is always paired with a jock /cheerleader instead of a fellow nerd.
I know opposites can attract and the heart wants what it wants (and obviously, nerd love is no more fail-safe than any other kind of love) but I will admit that one key to my nerd heart is someone who is just as big of a Rob Gordon as I am (okay, maybe not the key, but whatever it is, you could probably use it to pick the lock).
That said, I'd wager that the reason most people root for Duckie to get with Andie in Pretty In Pink is because we want to see him happy and if he thinks he'd be happy with her, we're with him all the way. But it's interesting that when we think about why we want him to be with Andie, it's not because they're some obvious match made in heaven. The reasons the movie gives us is that they're friends, she isn't wealthy, and they both have a unique sense of style. And Blaine isn't her friend, is wealthy, and is largely a square. Given two (and only two) options, of course we'd urge her to choose the former.
But why isn't there another option for the Duckies and the John Cusacks of the cinema world? Why is there a dearth of films where the Duckie of the piece is after someone like Allison from The Breakfast Club? Sure, that kind of happened in Mean Girls with Janis Ian and Kevin Gnapoor, but after that my example well runs pretty dry.
In the rare instance when a girl is depicted as a "nerd", she is usually little more than a prom queen wearing a too-tight Sega t-shirt (possibly paired with knee socks of some sort). Which is apparently all this character needs in a girlfriend: for her to be hot in the specific way he wants her to be hot with no expectations beyond that.
Imagine the female Duckie. Just for a minute. Kind of like a 16-year-old Cyndi Lauper, obsessed with records, dresses like a bad ass, funny and charming and strange; maybe a combination of Rayanne Graff from My So-Called Life and Watts from Some Kind Of Wonderful. Say she meets someone Duckie-esque. Would he go for her? Or would he go for the cheerleader who ultimately rejects him, causing him to realize his best friend isn't a bad second choice? It's hard to say and maybe the point is moot. Because the way popular cinema tells it, nerdy girls don't even exist (and if they do, they're comically "ugly" –- usually due to the addition of glasses).
I've known a fair number of offbeat women and if you ask, they'll tell you their one or more stories where guys were initially smitten with their endless knowledge of MST3K episodes, but left shortly after in search of someone less "complicated" (see: more comfortable taking a backseat in the relationship so he could "shine"). It's kind of like the "women are humor appreciators, men are humor generators" observation that forces me to audibly sigh upon remembering its existence.
But most of these screenwriters are post-college at the very least. You mean to tell me that not a one of them has dreamt of a nerd girl to call their very own? Really? They're still chasing the homecoming queen who has what they perceive to be some kind of hidden depth (see: capacity to want to fuck the less popular guy)?
Why isn't someone like Enid from Ghost World hanging out with the boys of The Big Bang Theory? Or someone like Casey from Party Down cracking jokes alongside Knocked Up's Ben Stone? Is it so hard to believe in the existence of women who are just as sharp, funny, and interesting as the men in these films? It must be, because the only romantic option for a nerdy male lead seems to be the "way out of his league" girl (who it would appear is adored primarily or solely because she is out of his league) who eventually loves him for who he is.
I'm not blaming anyone for wanting to be popular. Everyone in high school will at one point or another romanticize dating or befriending someone more popular than they are, even if only for 10 seconds. I'm also not saying that cheerleaders are worthless and vapid, just as I'm not going to sit here and say that all nerds are nice, lovable people. Good and bad exists in everything.
I'm just trying to figure out why the idea of an offbeat, interesting individual like Duckie wouldn't jump at the chance to be with someone who could match his knowledge of Otis Redding b-sides, school him in colorful secondhand vest options, and stand beside him as an equal, instead of a hard-won prize.