
Lily finds herself still in deep regret for pushing Ray away and out into the dating world, as he seems to have completely forgotten about ever liking Lily in the first place. Trying to win him back, Lily tells Ray that she knows a girl ""a lot like her that is interested in a guy like him that is looking for more then just a friend."" Ray responds that he knows ""a guy a lot like him that is also looking for more then a friend and would love to go out with lily"" So they agree to a date, and Lily thinks that Ray was talking about himself (since she was talking about herself) But it turns out Ray meant his church buddy mark and Lily has to frantically run around Mickey's trying to find someone that will go out with Ray. Meanwhile Robbie is jealous of Travis's worldly experience. note: this episode ends with Travis SINGING KARAOKE!
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.
Lily's friendship with Audrey seems to be on the upswing. Although they reunite and find common ground once again, Audrey's snobby attitude and elite posse, whose pastimes include ridiculing others, does not mesh well with Lily's kindhearted sensibilities. Lily suffers twinges of sadness when she opts for integrity and breaks off her friendship with Audrey but discovers a silver lining and new camaraderie in the hilarious and engaging Parker. Ray and Travis haggle over the gentleman's rules of romance that they are trying to establish in their pursuit of Lily, though each is only using ""the list"" to gain footing on the ever slippery slope to Lily's heart. Both Travis and Ray appeal to Robbie who is surreptitiously leads them to see that their sparring over Lily may in fact be the beginning to a beautiful friendship.