High school student Brendan Frye (Joseph Gordon-Levitt) lives a lonely existence following his breakup with ex-girlfriend Emily Kostich (Emilie de Ravin) and his betrayal of his friend Jerr to the authorities. Brendan discovers a note leading him to a pay phone, where he receives a call from a terrified Emily begging him for help. She mentions a "brick", "poor Frisco", "Tug", and "the Pin" before abruptly hanging up. Her fear appears to have been caused by a passing black Ford Mustang, from which a distinctive-looking cigarette was thrown. Upon asking for information from his nerd friend Brain (Matt O'Leary), Brendan's search for Emily sends him to another ex-girlfriend, "drama vamp" Kara (Meagan Good), which in turn leads him to a Halloween party attended by flirtatious upper-class popular girl Laura Dannon (Nora Zehetner) and her boyfriend, Brad Bramish (Brian J. White).