Plot hole: When the Chicago Post first runs the story on Kevin, there is a picture of him on the front page, next to the headline. So anyone who was following the story would have known what he looked like, which would make it impossible for Kevin's friends to get away with pretending to be him.
Continuity mistake: At the end of the movie, Kevin wants to meet "the L girl" at their stop at 7pm. While Kevin is waiting, the camera goes to the clock. First it says 7pm. After waiting a few minutes, it says 7:10pm. Then when Kevin finally gets to Abby, the clock in the background only says 6:55pm.
Other mistake: In one scene, Dan Montgomery is in his office when someone brings him one of the flyers Kevin had put up. When she enters the room Montgomery is playing a green Game Boy except there is no game loading into the Game Boy.
Trivia: Part of the movie was shot in Toronto (actually, the guys' apartment is in Toronto, I remember seeing interviews), along with where it takes place, Chicago. If you watch the credits and you watch where the cast is dancing while Al Green's singing, you can see a Tim Horton's Roll Up the Rim billboard in the background. Also, that scene takes place at the Eaton's Centre in Toronto.
Eric: Love may not make the world go round, but it makes the ride worth while.
Kevin Gibbons: Single White Male seeks commuter on train to share intimate secrets.
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