- 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.
- The Cast Showoff: Kirsten Dunst makes her singing debut with "Dream of Me", which is also included on the soundtrack.
- Dawson Casting:
- Ben Foster was twenty.
- Melissa Sagemiller was twenty-six.
- Sisqo, Zoe Saldaña 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 Saldaña'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.
- What Could Have Been:
- Josh Hartnett was conidered the role of Berke Landers.
- Aaliyah was in consideration for the role of Maggie.
- Working Title: Getting Over Allison.
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