The Dirty Sanchez (1999)

When young professional Damon is thrown out of his home by his wife he moves into the bachelor pad of his unsavory stepbrother Jamie Jamies friend Rob and unofficial roommate Casey Devastated by his breakup and naive to the wilder side of 90sstyle courtship the potential divorcée is shocked by the sexual gamesmanship of misogynistic Rob who has a dangerous taste for younger girls and adulterous Jamie who cheats on his nearperfect girlfriend to avoid working out their problems and finds himself the object of a highstakes game of chicken that no one can win