High school student Brad (Will Friedle) has had an unrequited love on a classmate named Brooke (Marley Shelton) for years. After she asks him to come over one night to tutor her, she ends up wanting to have sex with him. But she only wants safe sex, and he does not have a condom (the use of Trojan in the title is a pun on the Trojan (condoms)). In his quest to buy some condoms, he runs into all sorts of trouble; his dad's Jaguar Cars gets stolen and then wrecked, he has a run-in with a crazy bus driver (Anthony Michael Hall), he is held hostage, he is pursued by a school janitor (Paulo Tocha) who accuses him of drawing graffiti, an odd pair of Hispanic siblings (Christine Deaver and Mike Moroff) who thinks he looks like David Hasselhoff, Brooke's dog, Brooke's jealous boyfriend Kyle (Eric Balfour), and a homeless man (David Patrick Kelly) who wants two dollars from him (and has secretly stolen his wallet), and he is arrested.
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