Shy businessman Stanley finally gets up the nerve to ask out coworker Diana (Richards) after pining for her for a year. The night of the date, he hits a homeless guy Phil (screenwriter Lacopo) with his car, so Phil tags along. Stan also has to deal with a bunch of co-workers who've wagered on the outcome of the date, and are secretly monitoring the proceedings. Damon and Affleck's planned follow-up to "Good Will Hunting" sat on a shelf at Miramax for over two years, probably because of the inconsistent laughs and direction. Good cast does what it can with what it has to work with.