As single lawyers Rick Hamilton (SEAN PATRICK FLANERY) and Jane Bannister (AMANDA PEET) wake up in bed together, heavy with hangovers and wondering what they did the night before, Sara Olswang (TARA REID) suddenly shows up at their door.
Bleeding and dressed in a nightgown, Sarah claims that Rick's buddy, Michael Penorisi (JERRY O'CONNELL), a former pro football player, raped her. The story then shifts backwards a day as we see Rick and his three buddies, Michael, Shawn Denigan (BRAD ROWE) and Trent (RON LIVINGSTON) preparing for a night out on the town, while Jane and her girlfriends, Sarah, Whitney Bryant (EMILY PROCTER) and Emma Cooper (SYBIL TEMCHEN) do the same.
Planning to meet each other at a swinging nightclub, the members of each foursome discuss their views on relationships, love and sex. As the night wears on, members from each group eventually pair off for various romantic/sexual interludes, including Michael and Sara whose later encounter turns into a "he said, she said" debate over whether a rape actually occurred.
The following morning, as everyone tries to sort out the events surrounding the alleged rape, the members of each quartet react to that as well as their drunken dalliances from the night before.