The Third Wheel is a 2002 film directed by Jordan Brady. The plot of the movie revolves around a first date between the clumsy and shy Stanley (Luke Wilson) and the gorgeous Diana (Denise Richards) as their date is interrupted by a homeless man Phil (Jay Lacopo).
Stanley (Luke Wilson) is a nice guy and works in an office. Diana (Denise Richards) works at the same office and Stanley has had a crush on her for a while, but has a difficult time asking her out. When Stanley finally gets up his nerves to ask her for a date she accepts. As the two ventured out on their first date Stanley hits a homeless man Phil (Jay Lacopo) with his car, and the events that follow are far from the planned night of romance that Stanley had planned. All along this is happening Stan's co-workers that include his friend Michael (Ben Affleck) are monitoring the date between Stan and Diana, while they are betting on how far Stan will get with the beautiful Diana.