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.

After Deb's confession to have slept with Keith, Karen shows her the door and later has a misunderstanding which makes her break up with Andy. Haley chickens out on her music career at the last minute, so Chris leaves alone. When she gets home, her older sister Taylor is there. Nathan hopes she won't remember she was his first sex partner at a party in the beach house. They become friends and he decides she can stay a few weeks. Jake is back, without Jenny, for a few days he spends mainly with Peyton. Lucas finds out how Jules' poverty drove her to break Keith's heart. Felix has a fight with Lucas for 'hurting Anna' -who later confesses to Lucas she's just lesbian but hoped to be bi. Karen and Andy ultimately make up.