Felix puts together a "dare night" that tests the limits of his new classmates. During the game, Lucas meets a mysterious new girl, Anna, who is connected to the gang in a way they don't yet know while Peyton confesses to the church that she recently did cocaine. Meanwhile, Keith is caught of guard when a beautiful woman comes to the dealership to buy a car and the two end up hitting it off and Karen goes on a date with her professor, Andy.