Felix organizes a "dare night" to test the limits of his new classmates. While out playing the game, Lucas meets a mysterious new girl, Anna, and Peyton tearfully confesses to the church that she recently tried cocaine. Keith is caught off guard when a beautiful woman comes to the dealership and begins flirting with him. Meanwhile, Karen goes on a date with Andy, her younger professor. This episode is named after a song by The Replacements.