Although Nathan and Haley are already married, Tim insists on throwing Nathan a post-wedding bachelor party, while Brooke throws Haley a bachelorette party. Meanwhile, Lucas tries to decide whether he should visit Dan in the hospital. Karen decides to go back to school. Nathan gets a job working for Keith at Dan's dealership.

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. 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.