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 step-brother Jamie, Jamie's friend Rob, and unofficial roommate Casey. Devastated by his break-up and naive to the wilder side of 90s-style 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 near-perfect girlfriend to avoid working out their problems), and finds himself the object of a high-stakes game of chicken that no one can win.