Jake and Lorena decide that they don't have anything in common anymore. After they call it quits, Jake realizes that he still has feelings for him and Tiffani realizes that she still has feelings for Jake.

During Valentine's Day Tony realizes that he and Sam only have four months before Sam has to return to Hong Kong. He writes a special song for her and also decides to propose to her, so that they can stay together. The gang has doubts about whether she should accept.

Tiffani takes on the role of student principal for a week. Sam tries to tutor the gang in physics for their upcoming midterm. The gang decides to have a cut day during the midterm week while Tiffani is in charge.

It's Jake and Tiffani's three month and two day anniversary. Jake agrees to go on the dating game as contestants along with Sly and Tony. To Jake's surprise, he ends up winning the date, and decides to keep it a secret from Tiffani. She finds out, causing her to break up with him again. Meanwhile, Tony gets to meet his idol, gameshow host, Milt Bradley.

Using flashbacks from previous episodes, the gang puts Sly on trial for being the most greedy and selfish person in the world. Tony is defending Sly, while Tiffani is the prosecutor, and Jake becomes the judge.

In order to get the California Dreams a gig, Sly goes on a date with an overweight girl that he used to tease. He finally does get a conscience and starts to feel bad about using her. Meanwhile, a poem that Mark wrote for a crush goes from Mark to Lorena to Jake and then to Tony, making everyone think that the poem was written for them.

Sly is rude and makes fun of the ""Senior Surfers"". After having a dream that he is old, Sly decides to change his attitude toward the group.

After Sly causes Tony to hurt his shoulder, Tony must have an operation to repair his shoulder. Tony's afraid of having the surgery and believes that he will die. Meanwhile, Lorena decides to become a candystriper to get closer to Dr. Joe.

The gang gets involved in community service projects. Tony and Jake volunteer for Meals on Wheels, Mark cleans up the beach, Sam works for the blood drive, and Tiffany and Sly work at a teen help line. Sly is of course just doing the community service in order to meet girls.

With so much trash being discarded onto the beach, Tiffani and Mark decide to create an environmental group called Save the Beach. Tony gets too involved and the gang ruins his date with a girl that he likes. The gang also are wondering if Jake and Lorena like each other.

Sam's father gives her a credit card to use in case of emergencies. Sam goes a little overboard and ends up reaching the limit of the credit card. When she can't pay her father back, he threatens to make her return home to Hong Kong. The gang has to try and help her raise enough money to pay off the debt.

When Lorena's dad leaves her in charge of the ski lodge while he's away, she has Jake take over as the winter festival snow clown. Mark ends up running into his old girlfriend Jenny Stevens, who is an Olympic hopeful skier. She dumped him in order to try out for the United States National Ski Team. Meanwhile, Tony has a crush on a snow bunny.

Lorena wants to impress the new guy at school, Alan, so she decides to pretend that she's a poet. Sly and Mark want her to turn her loft into a coffe house while her parents are away. Lorena reads a poem that her father wrote for her mother, passing it off as her own. When Alan takes the poem, she has to think of a way to get it back from him.

Lorena enters a dance contest, but right before the contest, her dance partner gets injured. Sly wants to get closer to Lorena, so he tries to convince her to let him be her partner. Meanwhile, Tony argues with Jake about how the band should be run.