Lily starts getting the guys attention because she is hanging out with one of the prettiest girls in school. Lily's behavior has been different lately. She has been wearing dresses and flirting with cute guys. How come Ray seems to care so much? When he tries to sabotage Lilly's date with Lee Johns, Robbie and Travis are almost positive that Ray has stronger feelings about Lily than they thought. Maybe he likes her more than a friend. Will everyone's love life work out or will they all realise that loves really bites.

Travis and Audrey bond over their search for extra-terrestrial life, which inspires Travis to create a radio serial that reflects his feelings for her.

Travis convinces Lily to let him produce one of her songs. Travis is really tough but Lily realizes that he is bringing out the best of her musical talents. The song is an instant hit in Roscoe but Lily freaks out when he releases the single was aired under her own name as opposed to ""Shady Lane. As the accolades roll in, Lily learns to trust Travis and they grow closer than ever. Robbie and Kim realize they have great chemistry when they're debating issues against each other. Kim sees the on-air potential and asks Robbie to join her in a funny Cougar Radio segment. But it is hard to keep things light and funny when the gang has certain expectations of Robbie, and Kim's peers have certain expectations of her. Will the two of them be able to put aside their differences and concentrate on their shared love of radio?

The gang is reeling from secrets, betrayal, love and hurt feelings. Nobody but Question Mark wants to be at Radio Free Roscoe anymore. Like a lone wolf, Question Mark continues on his own trying to keep things together and hoping that everything will go back to way it was before it all fell apart. Travis is trying to keep things together with Audrey and Lily is just trying to figure out how she feels about everything and everyone. As RFR falls apart on the air, Principal Waller and Kim Carlisle come up with a plan that will take down Radio Free Roscoe once and for all and Robbie must make one of the biggest decisions of his life.

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.

After the Roscoe cheerleaders insult Lily and Parker, they team up with Travis to write a scathing song.