- Actor-Inspired Element: Julia's butterfly jean jacket actually belongs to Drew Barrymore. Director Frank Coraci liked her jacket and told her to wear it as part of her costume.
- Approval of God: Boy George found Alexis Arquette doing an impersonation of him and singing "Do You Really Want to Hurt Me" hilarious.
- California Doubling: The story is set in Ridgefield, New Jersey - indeed Glen works on Wall Street "in the city" presumably in Manhattan - but was filmed in California.
- Career Resurrection: After years of embracing a bad girl image, this film cemented Drew Barrymore as becoming a sweetheart romantic comedy actor.
- Defictionalization: A few bands have taken up the challenge of writing a song called "I Got Punched In The Nose For Sticking My Face In Other People's Business," the most popular one being from the emo band Boys Night Out. The closest there's ever been to a country song by that title is an indie folk track by The Man Who Loves You.
- Playing Against Type: Most of Adam Sandler's roles had been immature guys who eventually revealed a more sensitive side. This was the first role of his to be a fairly straightforward nice guy-with-underdog-tones, and that eventually became his new type.
- Release Date Change: The film was originally slated for a Fall 1997 release, but got pushed back by New Line Cinema to February 1998 as they felt the romantic comedy would perform better closer to Valentine's Day.
- Technology Marches On: Lampshaded; Glenn brags about buying a CD player for around $1000, and Julia promptly asks to play a record on it.
- Uncredited Role:
- Steve Buscemi and Jon Lovitz make unbilled cameos.
- Carrie Fisher did work on the script to make Julia's part more balanced. Judd Apatow, and Adam Sandler also performed uncredited rewrites.
- What Could Have Been:
- Christopher McDonald was considered for the role of Glenn.
- Betty White was considered for the role of Rosie.
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