When Stanley [Luke Wilson] meets Diana [Denise Richards] at work he knows she is the woman he has been waiting for. But hapless in love Stanley needs some help to secure a date and seeks advice from his friend Mike [Ben Affleck] before asking Diana out. Stanley cannot believe his luck when the beautiful, clever Diana agrees to go out for an evening with him. So with that obstacle over he thinks it should be plain sailing with his plans in place for the perfect date. However fate has other ideas and before the evening even kicks off Stanley and Diana bump into a homeless con-man named Phil [Jay Lacopo] who plays on Stanley's kind nature and upsets his potentially perfect evening in every way possible.