Stanley (Luke Wilson) has finally worked up the nerve to ask Diana, a co-worker he has been pining away for, on a date.

Stanley's best friend Michael (Ben Affleck) has helped him plan the perfect date. Stanley doesn't know that Michael has also set up a betting pool around his dream date and all his co-workers have money in the pot.

Stanley picks up Diana and everything seems to be going okay until Stanley ran into something that he never could have planned for: Phil. After accidentally hitting Phil with his car twice, Stanley and Diana are stuck with Phil for the whole evening. From the hospital to the theater to the bus to the impound lot a charming and comedic chain of events follows the couple throughout the evening as Stanley and Diana are unable to rid themselves of this third wheel.