Trojan War (1997)

Synopsis
In this randier-than-usual teen comedy, Brad (Will Friedle) is madly in love with Brooke (Marley Shelton), but she happens to have a boyfriend who is a star on the school football team. Brad's best friend Leah (Jennifer Love Hewitt) doesn't think much of Brooke or Brad's interest in her, but this is largely because she's secretly in love with him and wishes he felt the same way. Brooke is having problems with her boyfriend and decides she wants to make him jealous, so while Brad and Brooke are studying together, she tells him she'd be more than happy to have sex with him that night. Good news for Brad, but there's one small problem -- Brad doesn't happen to have any condoms, and as the evening wears on, he has a harder time finding some protection than any man since the dawn of time. Leah, of course, is heartbroken -- as much as she wants Brad to get what he wants, she knows that Brooke is merely using him, and would never give him the love she feels for him. Trojan War was also shown under the title Rescue Me. ~ Mark Deming, All Movie Guide