Jake realizes that he and Tiffani still have feelings for each other, with seriously complicates his relationship with Lorena. Meanwhile, Tony, Sly, and Mark take up ballet classes to get closer to women - but to his surprise, Tony ends up loving up.
As they get ready to celebrate their first Valentine's Day together, Tony and Sam realize that it may also be their last, since Sam will transfer back to Hong Kong at the end of the school year. Desperate to maintain their relationship they decide to get get engaged - much to the concern of the rest of the gang.
Principal Blumford makes Tiffani the school's student principal, and while at first she's scared of being in a leadership role, she quickly finds that she loves the power - maybe a little too much. Meanwhile, the rest of the gang worries about impending midterms.
To help out Sly and Mark, Jake agrees to participate in a dating game for charity. But to his surprise, he actually wins, meaning he has to go out on a date with another girl. And as luck would have it, their date falls on the night of his anniversary dinner with Tiffani.
Jake has a chance run in with his musical idol in Sharkey's, and the rocker actually agrees to give the Dreams a listen. Unfortunately, his intentions may not be as pure as they seem. Meanwhile, Tony suffers a bout of bad luck brought on by a cursed fortune cookie.
Sly feigns a romantic interest in a classmate so that she will agree to book the Dreams to play for her upcoming party. However, once feelings get involved, he realizes that his selfish agenda is not going to play out as easily as he expected. Meanwhile, Mark writes a love note to a girl he's crushing on, but when it falls into the wrong hands (repeatedly), it causes a lot of confusion and misplaced affection.
At first, Tony scoffs at Tiffani and Mark's concern for the environment after their favorite beach is shut down due to pollution. But after he realizes just how important an issue environmental awareness is, he not only joins their crusade, but goes overboard and becomes a nuisance to the rest of the gang.
While her parents are away celebrating their anniversary, Lorena decides to hold a coffee house-style poetry reading in her loft in order to impress a new guy who only seems interested in serious poets. But her deception goes too far when she loses the special poem her father wrote for her mother, and must find a way to replace it.
Lorena is faced with a tough decision when her partner for Sharkey's dance contest is injured; either forfeit the competition, or accept Sly's offer to fill the spot. Meanwhile, Tony decides that he should be the leader of the Dreams instead of Jake.