Saoirse Ronan's first kiss ever happened onscreen while filming this; she was 10 years old. She reportedly argued the kiss length down from ten seconds to five.
This movie sat on the shelf for a while with cast and crew wondering if/when it would ever be released. Finally, a theatrical release was agreed upon. However, a day before Michelle Pfeiffer (who had already given several magazine interviews promoting this movie) was to board a plane to begin publicity duties, it was announced that this movie would only play in limited markets before going straight to DVD.
"I Could Never Be Your Woman" was also a line from the song "Your Woman" by the musical group White Town and was also used in a scene in this movie.
Norm MacDonald was originally cast as Rosie's ex-husband. According to MacDonald, he grew a bushy mustache for the role. When writer and director Amy Heckerling told him to shave it off, he quit the project.