There's a Post-It note on the side of the monitor in the limo company office that says "call SoNo Studios" - that's where this film was made.
According to writer / director Bret Stern, Jorja Fox never auditioned for the role of Cheryl - instead he knew exactly who he wanted to play the role, so he sent her a copy of the script and asked her if she wanted the part. She read the script through and immediately said yes.
The wad of money (a prop) changes hands several times: from Cheryl to her bookie, from Cheryl to Chuck, from Chuck to his ex-wife, from Steve to Chuck, and from the bookie to Cheryl. The wad of cash is considered to be on the theme of life and money, and goes full circle from the beginning to the end of the film.
According to director Bret Stern, the scene where Chuck and Cheryl tear around in the dirt (leaving a heart carved with the tires) was a last minute addition to the shooting schedule.
The character of Gomes (Chuck's mechanic, played by John Sharian) was named after photographer Scott Gomes, whose photos of the screening in New York can be seen on the official Facebook page.