- California Doubling: The movie was filmed in Toronto.
- Dawson Casting:
- Ben Foster was twenty.
- Melissa Sagemiller was twenty-six.
- Sisqo, Zoe Saldana and Shane West were twenty-two.
- Colin Hanks was twenty-three.
- Christopher Jacot was twenty-one.
- Kylie Bax was twenty-five.
- Averted with Kirsten Dunst (eighteen) and Mila Kunis (seventeen).
- Executive Meddling: Several scenes had to be cut to get a PG-13 rating; Berke's parents' sex show had be toned down, the strip club scenes trimmed and certain antics at the party.
- Fake Brit: Baton Rouge native Shane West plays the very British Striker.
- Follow the Leader: Certain parts are clearly inspired by American Pie - the strip club, the house party, Berke's Butt-Monkey status. And of course this is one of many classical works of literature set in high school following Clueless's lead.
- Romance on the Set: Kirsten Dunst and Ben Foster dated for a few months after the movie.
- Technology Marches On: Berke's gift to Kelly - a voice recorder - could be achieved via a smartphone these days.
- Unintentional Period Piece: Striker is a member of a Boy Band whose music and image evokes the likes of Backstreet Boys and N*Sync, whose popularity would wane within a couple of years. Dennis references Titanic (1997), Berke's parents host a Point-and-Laugh Show and there are cameos from Vitamin C and Carmen Electra.
- What Could Have Been:
Trivia / Get Over It