- Billing Displacement: Sisqo is on the poster, despite playing the supporting character Dennis. Meanwhile Kirsten Dunst is front and centre, despite playing the Love Interest, and Ben Foster is the actual protagonist. Melissa Sagemiller and Shane West don't appear on the poster at all.
- 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. Also following the trend of having a Top 40 artist in a supporting role in a teen movie - in this case Sisqo as Berke's Token Black Friend.
- Playing Against Type:
- Ben Foster in his later roles would often be villains, psychos or morally ambiguous characters. Here he's the Butt-Monkey protagonist in a romantic comedy.
- This was one of Zoe Saldana's earlier roles, and she plays a high school Alpha Bitch (a role she also played in Crossroads (2002)).
- Melissa Sagemiller's earlier roles were usually wholesome Girl Next Doors. With Kirsten Dunst filling that role here, she's the Romantic False 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