Season 2 · Episode 1

Radio Free Roscoe: You Choose, You Lose

Friendships hang in the balance at Henry Roscoe High. Lily is torn between sheltering her strong friendships with Ray and Travis, and opting for romance. Travis reins in his affections for Lily when she pulls back from their near kiss, leaving Ray free to pursue Lily with an invitation to a ""special dinner"". Although the date turns from tragedy to triumph, Lily fears that a kiss could sour her friendship with Ray. Lily makes it clear that romance will not be in the air for either Travis or Ray, but the two suitors secretly throw down the gauntlet in pursuit of Lily's affections. And speaking of kissing… a rumor about Kim Carlisle snuggling up to a ninth grader races through the halls of H.R. High and reaches the ears of Principal Waller who squelches Kim's radio show with some super dull ""approved copy"". Kim's unhappiness strikes a chord in Robbie who persuades Waller to put the Carlisle ""You and Hello"" back in Cougar Radio.