On Valentine's Day, Tom (Cuba Gooding Jr.) stops at a local bar to down a glass of courage on his way home to ask his live-in lover to marry him. Seeing some of his best friends there, he invites them to drop by later for a celebratory party. However, when Tom arrives home, his lover is gone and a Dear John letter awaits him. As Tom's friends (Matthew Lillard, Mars Callahan, Sean Astin) drop in, the group begins an alcohol-fueled discussion about love and relationships.