Sorority Boys (2002)

Dave (Barry Watson), Adam (Michael Rosenbaum) and Doofer (Harland Williams) are about to go where no frat boy has gone before. They're three playboy chauvinists who, 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," they go undercover as Daisy, Adina and Roberta. Everying goes fine until Dave falls for Leah (Melissa Sagemiller), the alpha D.O.G. The boys see firsthand how the other half lives and their history of treating women badly comes back to haunt them when they walk a mile in their 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?