RJ gets asked to join Hamilton's "badass" crew, after rumours circulate about him popping pills. Meanwhile, Lily attempts to join the cheerleading squad in the hopes of catching more of RJ's attention, and she unexpectedly connects with Jenny.
RJ's parents go out of town for a getaway weekend, leaving a hot babysitter named Jenni in charge. Miles throws a party which gets completely out of hand while RJ continually tries to impress the babysitter, which doesn't end well.
RJ wants to take his relationship with Claire to the next level, physically, but goes about it all the wrong way, by taking advice from all the wrong people, and by lying. Miles also pays the price for a lie.
RJ starts to work for the highly sexual Mrs. Robbins, in order to pay for a 16th birthday gift for Jenny. Meanwhile, he and Miles have a major falling out because of it, which they have to try to repair.
In the premiere, RJ is forced to play in the school basketball game. Unfortunately for him, his shorts fall down and his not so little secret is exposed to the whole school. Now RJ must deal with the humiliation at school. He also attends Jenny Swanson's party.
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