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.

In order to raise some money for the H.A.H.A.A.A. Benefit, Riley and Chloe enlist the help of the others for a screenplay that they wrote. The others, thinking that big-time producer ""Marvin Dobbs"" is involved, agree to help them. Meanwhile, Manuelo gets in trouble with Mel Gibson's security guards when he keeps trying to reach him about how many tickets he wants for the play.

When Larry deletes Macy's tax returns by accident, he brings his father, Roger, over to help, but he ends up falling in love with Macy. So she tries desperately to find a way to break up with him without hurting his feelings, and enlists Tedi to help her. Meanwhile, Jake ends up making Riley and Chloe's teacher, Miss Westmore, fall in love with him by accident. Now he, too, has to find a way to break up with her.

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.

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.

Todd sees Riley sitting in a wheelchair and instantly believes she, too, is not able to walk and is forced to be in a wheelchair, just like he is. But the guilt is too much for Riley and wants to tell him the truth before it's too late. Meanwhile, when Macy and Jake leave for the night to go on a date together, Chloe and Lennon decide to throw a party at the house, but it gets cut short when Macy and Jake arrive home early.

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.

Chloe and Riley sign up for elective courses in cooking and sewing, then find they are sorely lacking in skills to do the work. Chloe ""borrows"" some of Manuelo's recipes for her cooking assignments, while Larry, who discovers he has a natural talent for fashion design, covers for Riley and lets her be graded for his project. Unfortunately, the whole thing blows up in their faces when Jake and Macy try to impress a magazine reporter by having the girls show off their ""talent.""

When Jake, Macy, and Manuelo offer to give the girls a huge Sweet 16 party for their birthday, Riley and Chloe refuse in favor of some quiet time alone instead. After overhearing Manuelo on the phone talking about what they think is their Sweet 16 party, Chloe and Riley start to think about it and decide that a Sweet 16 party might not be so bad, after all. Once they arrive at the News Stand, they come to the conclusion that they might've arrived on the wrong night, due to the fact that they don't recognize anyone there.

Chloe learns that boys are just like dogs, and can be treated in a similar fashion. Meanwhile, a nervous Macy tries designing a dress for Teddie, only to find it's exactly the same as another dress someone else is already wearing. So, Riley asks Jake to help a reluctant Macy with her dress.

When the family learns about the ""Save the Seals"" Benefit Dance, they all scramble to find dates. Chloe decides to try and get Travis to go with her, while Riley tries desperately to find someone other than Larry. Meanwhile, Macy and Jake try their luck by going out with different people.

Larry gets his friend, Tony, to persuade Riley that he's a great catch. But it backfires when Tony tries to woo her himself. This is all put on hold when the Carlson's home is threatened by a fire. Meanwhile, Macy becomes jealous when Teddie helps to rescue Jake from the trailer.

Tedi decides to quit modeling over a craving for onion rings. As a debate partner for a school project on capital punishment, Chloe pairs off with a boy she admires. This makes Riley really angry at her and she pairs off with Larry, who usually gets the giggles every time.

Chloe becomes angry with the new guy, Lennon, after he keeps taking the last blueberry muffin at the News Stand. To make matters worse for her, he also happens to be a student at her school. Meanwhile, Riley tries to comfort her new friend, Cammie, by introducing her to Larry, who is still obsessed with Riley. Back at the house, Macy and Jake date people who not only look like each other, but also act like them.

Chloe and Riley get jobs as waitresses at the Newsstand. But when they get to their customers, they realize that becoming a waitress is not the kind of job they wanted. Back at home, Macy and Jake meet a couple who are trying to rekindle their relationship.

When Chloe and Riley team up with Larry for a school project, he ruins their first attempt and then tries to redeem himself by constructing a state-of-the-art weather station.

Riley and Chloe find that they have no money for a concert they want to go to, so Larry surprises them by buying three tickets to the concert. The day after the concert, the money from their school fundraiser is missing, and immediately suspect Larry of taking it. Meanwhile, Manuelo finds it hard to spend some time with his girlfriend, Khandi, since Jake keeps interfering.

Riley gets too caught up when she receives this great massage. After she finds out about Riley and this massage, Macy gets the same treatment Riley did.

While the cable goes out all over town, the Carlsons and Manuelo reminisce about each of their experiences from previous episodes.

Chloe gets a driving lesson from Jake and Riley gets hers from Macy. Then they both get another lesson from a driving instructor. But when it is all said and done, Chloe is the driver and they get a flat tire but the instructor gets a phone call and has to go away. Chloe and Riley meet a boy who notices them having car trouble and takes off with the car. When the instructor comes back he is disappointed to see that the car is missing.

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.

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.

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.

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.

When Chloe ""adopts"" a new grandmother, Riley tries to as well. The only problem is that she keeps killing off her potential grandparents.