Sorority Boys (2002)

Three playboy chauvanists, strapped for cash, find themselves drawn to one last, desperate hope for free housing: one of their campus' sororities, Delta Omicron Gamma (or D.O.G.). With a little make-up, a little pantyhose, and lots of "pluck", Dave, Adam and Doofer go undercover in the sorority house as Daisy, Adina and Roberta. Everything goes according to plan... until Dave falls for Leah, the alpha D.O.G. Life's a drag as the boys see firsthand how the other half lives--their history of treating women badly comes back to haunt them when they walk a mile in another's (high-heeled) shoes. Meanwhile, Dave wants to tell Leah about who he really is, but without destroying "Daisy's" relationship with the girl of his dreams. What's a boy (pretending to be a girl) to do?