When Garry Marshall's character is speaking to his employees at the Chicago Sun-Times board room, he says, "I don't even know my own kids." His real-life daughter, Kathleen Marshall, is sitting to his right when he's speaking.
Leelee Sobieski was originally offered the role of Kristin but she opted to play the role of Aldys instead finding that character more interesting.
It is an issue in the movie that Josie is considerably older than her "high school crush" Guy (she is supposed to be 25, while he would be about 17), but actually, Drew Barrymore is 2 years younger than Jeremy Jordan, the actor who plays Guy.