Felix (Michael Copon) organizes a "dare night" to test the limits of his new classmates. While out playing the game, Lucas (Chad Michael Murray) meets a mysterious new girl, Anna (Daniella Alonso). Peyton tearfully (Hilarie Burton) confesses to the church that she recently tried cocaine and Keith (Craig Sheffer) is caught off guard when a beautiful woman (guest star Maria Menounos) comes to the shop and begins flirting with him. Meanwhile, Karen (Moira Kelly) goes on a date with Andy (guest star Kieren Huchison), her younger professor.