Trojan War is a romantic comedy about unrequited love and the search for just one condom. The would-be Casanova is Brad (Will Friedle), a high school senior who harbors a long-time crush on his classmate Brooke (Marley Shelton). Brooke wants to make her jock boyfriend (Eric Balfour) jealous, so she invites Brad over one night under the pretense of tutoring. Brad thinks his dreams of love may finally be coming true, but he needs a condom, and this quest turns into one long night of misadventures. Through all the mishaps, Brad's best friend Leah (Jennifer Love Hewitt) is by his side, hiding the fact that she is secretly in love with Brad. This teen love story is full of witty references to other classic movies of its genre. Actor Anthony Michael Hall, who starred in many coming-of-age comedies in the 1980s, makes an appearance as a crazy bus driver who insists that passengers have the exact change.