When Riley, gets approached by a Gothic Girl for her notes, because if she doesn't pass this history test, her mother would ground her and she can't go to the party. The girl promises Riley and Chloe to have them over for a party, here at school. Chloe has an outburst, saying that Riley can tutor her, too. Riley and Chloe doesn't know how to handle is situation, so when the girl comes over they dress Gothic.

They tutor her, and she pass with a B+. She tells them that the party will be at Midnight. Riley and Chloe are pretty nervous about how to attend the party, so they have a plan to leave late, because that what cool kids do. But the truth is that they are scared, and doesn't want to go. So they fall asleep on the bed.

Thinking that they are at the party, Larry wants to take them both out. He tries to sneak in but they kick him out. He then sneaks in as Britney Spears, and asks the girl where was Chloe and Riley. He then says that they never showed up.

Larry then gets hit on a guy, thinking that he is a girl.

In the morning, Chloe and Riley blames each other for not going to the party. They are then greeted by Larry in the whole Britney Spears costume, and he tells them to hide him.

Macy wants to meet an old high school flame when Jake decides to read her private e-mail. Meanwhile, Chloe, Riley, and Larry have to perform community services.

Riley and Chloe manage to get Teddie and Manuelo for Career Day at school instead of their parents, who would have ruined it for them. Meanwhile, Macy plans for a new family portrait, and unknowingly doesn't include Manuelo in it. This prompts Manuelo to become extremely upset and eventually quit, since he believes, in their eyes, he's just a simple employee.

The Carlsons' continue searching for Manuelo throughout Malibu. Meanwhile, while working at Neptune's Net, Larry finds Manuelo to be the new chef there. However, he is blackmailed into maintaining his secret.

When some seniors advise the girls to look into college entrance information early, Chloe and Riley discover that they're interested in different schools and decide to try a ""trial separation"" to see how it would be like living apart from one another. Larry winds up being the go between for the girls, helping them to decide what to wear after they come to school in the same outfit; unfortunately, he loses it after a long cram session that requires him to keep running back and forth from Jake's trailer and Macy's house to study with both girls. Macy and Jake, growing tired of finding other people to date, decide to start over and have ""first dates"" as if they never met before as a method of rekindling the sparks.

When Travis gets detention at school, Chloe decides to also get detention to spend some time with him. So she tries to get in trouble with something major to impress him, but she soon learns getting detention is harder than it looks, and ends up getting everyone else except herself in detention. Meanwhile, Riley attempts to give Larry a chance at getting to know him better, and discovers he is even worse than she thought he'd be.

Riley must deal with unsavory rumors being spread about her by a previous date and a young musician she is absolutely smitten over. Chloe tries every trick in the book to land Lennon as a boyfriend and fails, until she throws the book away.

Riley and Chloe decide to create their own rock band and enter a ""battle of the bands"" contest at school. However, the only musicians they are able to recruit are Larry and Randy, the school nerd.