In order to beat their rivals, Bradley and the Billionaires, in Sharkey's Battle of the Bands competition, the gang encourages Matt to go out with the slightly-geeky Angela, who happens to be one of the judges. Matt begins to doubt whether he can go through with it, though, when he actually starts to develop feelings for her. Meanwhile, the girls tease Tony for being too afraid to go through with getting his ear pierced - and refusing to admit it.
Tony quits the band and joins the football team to please his father, who sees the band as just a hobby and believes that sports offer Tony more of a future. Meanwhile, Tiffani has an unlikely secret admirer.
When Sharkey leaves Tony in charge of his restaurant for a week, Sly convinces him to "borrow" some money from the cash register and throw a luau party (featuring a performance by the Dreams) in order to earn a little extra money. Things get complicated, though, when Matt books the Dreams to play for a wedding on the same night. With canceling either gig out of the question, the band has to figure out how to make it work.
Sly overhears Jenny describing her "dream man," and then proceeds to try to make himself into her ideal mate. Meanwhile, Matt doesn't know how to tell Tiffani that her new song lyrics leave something to be desired.
Jenny and Tiffani go from friends to rivals when they both begin dating the same guy, and Matt worries about the affect that their rift might have on the band, especially with a big audition at Sharkey's coming up.
After Jenny and Tiffani come up with a scheme to teach Tony and Sly a lesson about how to treat women with respect, a battle of the sexes ensues. Meanwhile, Melody becomes frustrated with Richard, Matt, and Dennis, who insist on asserting their manliness by fixing things around the house, but only make things worse.
Tiffani's mother comes back to town for the first time after she abandoned her family ten years before. Tiffani surprises everyone when she is thrilled about the situation, but Jenny suspects that she might be holding back some anger.
Sly enlists Tiffani to give him surfing lessons in the hopes that it might help him get girls. But to everyone's surprise, they end up falling for each other. However, Sly immediately begins to feel smothered and tries to get Tiffani to break it off. Elsewhere, Matt, Jenny, and Tony convince Melody to pay them the money they need for some lighting equipment if they paint a bedroom.
Jenny assumes the best when her ex-boyfriend suggests that they get back together. But Matt worries that he's too self-centered, and his fears are confirmed when he convinces Jenny to skip band practices and gigs in order to spend time with him.
When their parents go away for the weekend, Matt is left in charge of Jenny and Dennis. When he breaks the rules and agrees to let Sly offer up the house for a party, Dennis feels left out and runs away. Meanwhile, Jenny gets fed up with her boyfriend's predictability.