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1* BillingDisplacement: Sisqo is on the poster, despite playing the supporting character Dennis. Meanwhile, Creator/KirstenDunst is front and centre, despite playing the LoveInterest, and Ben Foster is the actual protagonist. Melissa Sagemiller and Shane West don't appear on the poster at all.
2* CaliforniaDoubling: The movie was filmed in Toronto.
3* TheCastShowoff: Creator/KirstenDunst makes her singing debut with "Dream of Me", which is also included on the soundtrack.
4* DawsonCasting:
5** Creator/BenFoster was twenty.
6** Melissa Sagemiller was twenty-six.
7** Sisqo, Creator/ZoeSaldana and Shane West were twenty-two.
8** Creator/ColinHanks was twenty-three.
9** Creator/ChristopherJacot was twenty-one.
10** Kylie Bax was twenty-five.
11** Averted with Creator/KirstenDunst (eighteen) and Creator/MilaKunis (seventeen).
12* ExecutiveMeddling: 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.
13* FakeBrit: Baton Rouge native Shane West plays the very British Striker.
14* FollowTheLeader: Certain parts are clearly inspired by ''Film/AmericanPie'' - the strip club, the house party, Berke's ButtMonkey status. And of course this is one of many classical works of literature set in high school following ''{{Film/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 TokenBlackFriend.
15* PlayingAgainstType:
16** Creator/BenFoster in his later roles would often be villains, psychos or morally ambiguous characters. Here he's the ButtMonkey protagonist in a romantic comedy.
17** This was one of Creator/ZoeSaldana's earlier roles, and she plays a high school AlphaBitch (a role she also played in ''{{Film/Crossroads 2002}}'').
18** Melissa Sagemiller's earlier roles were usually wholesome {{Girl Next Door}}s. With Creator/KirstenDunst filling that role here, she's the RomanticFalseLead.
19* RomanceOnTheSet: Creator/KirstenDunst and Creator/BenFoster dated for a few months after the movie.
20* TechnologyMarchesOn: Berke's gift to Kelly - a voice recorder - could be achieved via a smartphone these days.
21* WhatCouldHaveBeen:
22** Creator/JoshHartnett was conidered the role of Berke Landers.
23** Music/{{Aaliyah}} was in consideration for the role of Maggie.
24* WorkingTitle: ''Getting Over Allison''.

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