An unlucky-in-love bachelor lands his dream date, but finds that getting through the evening will be a difficult challenge indeed in this romantic comedy. The Third Wheel stars Luke Wilson as Stanley, a woefully inept young man who -- with the aid of his roommate Mike (Ben Affleck) -- works up the nerve to ask out his alluring co-worker Diana (Denise Richards). Diana agrees, but before the two can even be seated at a restaurant, they literally run into a homeless con man named Phil (Jay Lacopo). Currying pity from the hapless Stanley, Phil proceeds to disrupt the evening in every way imaginable. One of the first films from Matt Damon and Ben Affleck's production company, The Third Wheel languished on the shelf for more than three years; a similar, if less-severe, fate befell Wakin' Up in Reno, another Miramax-distributed comedy also directed by Jordan Brady.
~ Michael Hastings, All Movie Guide