In Made of Honor (and probably real life), Patrick Dempsey is the epitome of a douchebag--a basketball-playing, covertible-driving, nerd-mocking, womanizing asshole. In other words, he's the perfect antagonist to the geeky yet lovable underdog who is ultimately meant to get the girl in the end.
Yet, for reasons I still can't grasp, Dempsey is the one we're meant to be cheering for as he tries to stop his love from marrying a man who, by default, must be less of a dick. To keep us distracted from how much we should hate the McDreamy protagonist, he's given the role of maid of honor, providing many opportunities for men-don't-understand-lady-stuff and gay jokes as he reclaims his undeserved lady. Duckie must be rolling in his grave (a shallow hole the exact shape of Two and a Half Men).