Are there any movies that reverse the usual teen romance cliche?

Not a parody, but Win a Date With Tad Hamilton sorta does this. Hamilton is a rich celebrity the main girl is in love with, while Topher Grace works in a grocery store. Main girl's dad tells Grace "I was rooting for you", or something to that effect.

I don't really remember the parent situations in these movies, but we're supposed to be rooting for the rich boys in Pretty In Pink and that cheesy sh*tshow Here on Earth.