In one version of the scene where Martin walks into Debi's radio booth for the first time, Minnie Driver decided to let her character put all the cards on the table and just kiss John Cusack. George Armitage said, "It was just wonderful, completely out of the blue. You should have seen the smile on Johnny's face afterwards."
Jenna Elfman wearing a body brace at the dance is a tribute to Joan Cusack in Sixteen Candles (1984).
Features appearances by most of the acting members of the Cusack family: John Cusack, Joan Cusack, Ann Cusack and Bill Cusack. Only one sister, Susie Cusack and father Dick Cusack, are absent.
Martin's invitation to his high school reunion, which is tucked into the mirror as he gets ready, requires attendees to Dress to Kill.