Sly's trying to find a date for the Romance Dance at school. So, he heads online and meets a girl, Allison, on the online chat room ""Comp-U-Chat"". When he finally meets her, he finds out that she's blind. After seeing Sly's good luck getting a date, Tony and Sam decide to give ""Comp-U-Chat"" a try for themselves.

Jake enters a motorcycle contest and Uncle Frank pays a visit to help Jake win the competition. Uncle Frank gets Jake hooked on smoking. The whole gang thinks that smoking is a bad idea, especially Lorena. She threatens to not date Jake anymore if he doesn't quit. The band also finds a box filled with money on the beach. Mark is left in charge of it and Sly thinks investing the money in a get-rich-quick program is a good idea.

While trying out for a spot on the National Volleyball Team, Tiffani realizes that her small size is keeping her from being the best. Sly suggests that Tiffani takes steroids to make her bigger and stronger. The band soon realizes that Tiffani is addicted to them. Sam and Lorena also have a studs contest featuring Tony, Sly, and Mark as contestants to see which one of the guys is the best with the ladies.

Everyone takes a career aptitude test at school that will tell them what career would be perfect for them. Mark a guidance counselor, Sam a photographer, Tiffani a veteranarian, Jake a florist, and Lorena and Sly both a fashion designer. In trying to get a date with Lorena, Sly copied off of her test so that they would have more in common with each other. While Jake has trouble writing a new song, he decides to work on his new florist career.

After Allison announces that she's going away to another school, Sly is heartbroken. Lorena and Sam accuse Jake and Tony of not being as romantic as Sly. Jake and Tony try to prove that they are romantic, too.

Lorena makes a bet with Jake that greed can rip apart friendship, even the band's friendship. Lorena and Jake create a plan to make the gang believe that there is buried treasure hidden nearby. Lorena's right- friendships start to get strained. Both Jake and Lorena end up surprised at the extent of everyone's greed.

Lorena loves working on the school radio station, but due to budget cuts, the station will be closed. She takes Jake's advice to try and keep it open. Mark also does an on-air review of Tony's play ""Hamlet"".

It's time for another battle of the bands. This time the California Dreams are against the rap group Total Defiance. Managed by Rosie, Sly in the form of a girl. After Total Defiance says that Lorena is just a groupie, she wants to join the band. When she auditions, the band realizes that she can't sing at all. They don't want to hurt her feelings and tell her, especially Jake.

Lorena's father hires the band to play at his ski resort in Colorado. During their stay they run into some weird things, including an old mountain man and a Yeti driving the guests away from the resort.

Not wanting her dad to be alone, Tiffani sets her father, Paul, up with marine biologist Ariel. This turns out to be a bad idea when Tiffani's dad spends all his time with Ariel instead of Tiffani. Mark creates a compatability test that claims that Tony and Sam aren't compatabile as well as Jake and Lorena. The couples start arguing over the results.

The new guy at school, Tommy Keating, bad-mouths Jake around the school. After Tommy challenges Jake to a motorcyle race, Jake accepts. After hitting a speed bump at Sharkey's, Jake crashes his bike and doesn't compete in the race, resulting in being accused of being a coward. Tony and Sly also become school safety monitors.

The band must work on a project for school, creating their own television shows. Tiffani and Mark partner up to create ""Ms. Smith's Neighborhood"", which is a cross between a surfing show and ""Mr. Roger's Oceanside."" Jake, Lorena, and Sam partner up to create ""Hall Monitors,"" a take-off on ""Cops."" While Sly and Tony create ""The Goo-Ga-Moo Guys,"" a ""Wayne's World""-type show for guys that are interested in girls. ""The Goo-Ga-Moo Guys"" becomes a hit show on a local station and Sly quits being manager of the band. However, Sly and Tony's friendship gets strained over greed.

An old friend from Tony's childhood, Darren, pays a visit to Tony. He aks Tony to help out one of their friends from a gang that he's joined. The friend ends up in the hospital and Tony has to decide if he should help get revenge on the gang. The rest of the band takes a job delivering singing telegrams.

After the Garrison family moves away, including Matt, Sam moves in with Lorena Costa. The band also get to use her place to practice from now on. Unfortunately, all their equipment is at a pawn shop and they have to get it back. They also need to find a replacement for Matt. Sly thinks that his cousin, Mark, might be right for the job, but Mark has had a bad case of stage fright ever since Sly embarrased him at Carnegie Hall.

The gang is assigned a school project to research their family tree and give a report. Tony isn't able to find anything about his family past the Civil War. Embarrassed, Tony lies about his family's background. Sly and Mark give a speech about their ancestors who had the Winkle charm, and try to use it on girls.

The gang competes in a video competition. When trying to write a new song, Mark spends a lot of time at Lorena's house. They end up kissing and Mark tries to find a way to confess to Jake without getting the pulp beat out of him.

For an economics project at school, the gang decides to sell Sam's Great Great Grandmother's cold remedy. Sam is overwhelmed with greed, and later has to decide what's more important- money or her Great Great Grandmother's honor. Jake and Mark decide to create their own business as music teachers.