Trojan War (1997)
IMDb synopsis (edited): High school student Brad (Will Friedle) has had an unrequited crush 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 an obvious pun on the condom brand.) In his quest to buy some condoms, he runs into all sorts of trouble, including having his dad's Jaguar stolen then wrecked; having a run-in with a crazy bus driver (Anthony Michael Hall); being pursued by a school janitor (Paulo Tocha); and having a run-in with Brooke's jealous boyfriend, Kyle (Eric Balfour). Then, there's the homeless man (David Patrick Kelly) who wants two dollars from him~but secretly stole his wallet. After all of this, he realizes that the perfect girl has been there for him all along: his best friend, Leah (Jennifer Love Hewitt).