Season 2 opens on a confused RJ, who is haunted by his friend Lily while yearning for his dream girl Jenny Swanson. Also, Miles deals with the ramifications for ball-beating Pinkerton's top dog, Max Owens.

In an attempt to win over the girl of his dreams, RJ asks Jenny on a date. When she says "yes," he and Miles prepare with a G-T-L makeover from Cousin Vinny (Jersey Shore's Vinny Guadagnino).

It's "Lock-In Night" at Pinkerton, and RJ finally gets the chance to have sex with Jenny, but a bitter Lily Miran will do everything she can to make sure that doesn't happen.

When Jenny suffers a breakout, RJ questions the depth of their relationship. At the same time, Lily receives her settlement from the bus accident and experiences her first taste of popularity.

Distracted by problems with Jenny and his parents, RJ's grades start to slip. When he's forced to see a tutor, she offers him more than just academic advice. Meanwhile, Miles gets seduced by his teacher.

When RJ gets caught in a lie, his relationship with Jenny falters. In her absence, Amy joins RJ on a quest to save his drunk, depressed, and unemployed father.

On the eve of their 20th anniversary, RJ's parents invite him to dueling dinners, and RJ is forced to choose between his mom and his dad. Meanwhile, Miles joins the cheerleading squad to lose weight.

With his 16th birthday rapidly approaching, RJ asks his dad for driving lessons. He gets way more than he bargained for when Rick takes him to Hunkeez, a male strip club.

After years of having his birthday ruined by Max Owens, RJ and his friends decide to throw a "Max Bash." When Max and his gang of jocks show up at the party, things get out of hand.

RJ finds out Max's "steamy secret," and things get complicated with Amy when he gets nominated for "Mr. and Miss Pinkerton" with ex-girlfriend, Jenny.

RJ receives shocking news from Lily and faces off with Max Owens for the title of "Mr. Pinkerton."