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 the two of them seem to hit it off. Peyton tearfully confesses to the church that she recently tried cocaine and Keith is caught off guard when a beautiful woman comes to the shop and begins flirting with him. Meanwhile, Karen goes on a date with Andy, her younger professor.

Haley is surprised when her older sister Taylor comes to town, but not as shocked as Nathan, who recognizes Taylor from a past tryst. Brooke and Felix decide to become boyfriend and girlfriend. Jake makes a special visit to Peyton. Anna tells a secret to Lucas.