her physical appearance. He suffered a number of losses early in life, including the death of his mother and the "suicide" of his cat. He also has an older brother named Chet, who is shown to be a crazy Iraq War veteran. He lost his virginity to a substitute teacher which resulted in him catching crabs. Kara Taitz as Lily Miran, a socially awkward, and sex-obsessed girl who is infatuated with RJ and constantly chases him, much to his dismay. She has an unusual fashion sense and is frequently dyeing her hair; it is revealed that she makes her own clothes in episode 11. She and Miles constantly antagonize one another. RJ asks Lily to the school dance, much to her delight, but she was hit by a bus before the dance. Out of pity, RJ agrees to have sex with her. After she finds out RJ and Jenny are dating, Lily tries to sabotage their relationship at any cost. She and RJ eventually rekindle their friendship; she even sparks a friendship with Jenny. Lily briefly dates Hamilton but reveals to RJ that she is pregnant with his baby in the final minutes of Season 2, setting up for a non-existent Season 3. Jayson Blair as Max Owens, an arrogant and obnoxious school jock and RJ's main antagonist. After RJ stood up to him in the first episode, Max swore to humiliate RJ at all costs as a punishment. He was Jenny's boyfriend in the first season and is aware of RJ's crush on her, which makes him jealous. In the season finale, just as Max is about to fight RJ for kissing Jenny, Miles tackles him and starts punching him repeatedly in the testicles, giving RJ the chance to leave. When RJ and Jenny begin dating, he dates Robin Pretnar, Jenny's best friend and head cheerleader. In the second season, RJ discovers that Max is secretly gay and RJ agrees to keep his secret. Amber Lancaster as Jenny Swanson, RJ's primary love interest; a beautiful, popular, and down-to-earth cheerleader. She is impressed with RJ after he stands up to her boyfriend, Max, and by RJ's overall kindness. In the season finale, RJ and Jenny share a kiss before a concerned RJ returns to Lily's hospital bed. She and RJ begin a relationship in season two although they eventually break up, due to the fact they have no similar interests