5. I Will Dare

Felix organizes a "dare night" to test the limits of his new classmates. While out playing the game, Lucas has to return clothes to a store whilst wearing them. An unknown girl helps him out when security come to get him: it is Anna, who joins in further dares. Peyton is dared to confess in church with something rude, but in the confessional she admits this is the first time she's been in church since her mother died. Tearfully she admits that she recently tried cocaine and hopes her mother didn't see.

Keith is caught off guard when a beautiful woman, Jules, comes to the dealership and begins flirting with him. Meanwhile, Karen goes on a date with Andy, her teacher. Brooke gets angry with Felix when he dares her to 'dine and dash' without paying the bill. Lucas takes a liking to Anna, who is revealed to be Felix's sister. This episode is named after a song by The Replacements.