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Chris and Jamal end up in jail after getting caught with fake IDs. But the situation worsens when Al and El-Train (Steven Daniel) come to bail the guys out and end up behind bars as well. Meanwhile, Dawn and Cassidy offer their tutoring services at the school fundraising auction, but they're worried that Vinnie and Rocco have more than tutoring on their minds when they bid on the girls.
Chris and Jamal uncover the school's old radio station. The station is restarted and quickly ended after an unapproved song gets played on the air. The boys now have to figure out how to get the station back on the air.
El-Train has a fight with his mom and decides to move out of his home. But when Chris lets El-Train stay at his Park Avenue penthouse, he soon realizes that El-Train isn't interested in going back home anytime soon, so he has to come up with a plan to get El-Train back with his mother. Meanwhile, Al asks Cassidy and Dawn to be models for a photo shoot, but the girls become angered when they see where the photos end up.
After being robbed at gunpoint during the nighttime, Jamal buys a gun himself to feel safe.
Chris finds out that his parents are getting a divorce, he becomes a recluse and blames himself for their breakup. But his friends help him realize that it was not his fault and that he should talk things out with his parents.
After El-Train beats up a local bully, he starts reverting back to his own days of bullying people, and even begins to isolate his friends. But when Miss Noble gets ahold of him, she reminds him of how far he's come, forcing him to think twice about his attitude, and his next schoolyard fight. Meanwhile, Dawn is embarrassed after a terrible date with school quarterback Brent (guest star Scott Hamm), where she tried to pass herself off as a football expert and ended up looking like a fool.
Jamal asks Cassidy if she can get her new boyfriend, 98 singer Nick Lachey, to perform with the rest of the group at an 'unofficial' school dance on the roof of Manhattan High. Although the dance is supposed to be kept a secret from Miss Noble, the gang soon realizes the consequences of trying to fool the principal.
Chris decides to go on a date with one of the callers to his radio show, but when he sees that she dresses like a Goth, he is unsure about whether or not to go out with her again, even though he likes her. Meanwhile, El-Train leads the gang in throwing a surprise party for Miss Noble's tenth anniversary at Manny High.
Miss Noble asks Jamal and Chris to become big brothers as part of a class project. But their little brother, Ernesto, turns out to be a handful of trouble, especially when he keeps disappearing on the guys. Meanwhile, Cassidy tries to pass Driver's Education again, but first she has to get by the very strict teacher's assistant, El-Train.
Cassidy starts taking pills when she is overworked.
Ms. Noble quits after the students take her for grant one too many time. She returns when her replacement gets out of control.
During his radio show, Jamal advises an anonymous caller to drop her current boyfriend for the guy she has a crush on, but doesn't realize that Al is going to be the one cut loose. The situation worsens when Jamal finds out her crush is on him, so he concocts a plan to get her to stop liking him. Meanwhile, El-Train sees Dawn's comet viewing party as an opportunity to signal aliens and befriend them.
When El-Train continues having problems with his test scores in school, he decides to drop out and join the Marines. He becomes even more distraught when he fails the Marines' admission test, until someone discovers that El-Train may be suffering from dyslexia.
The gang help AL and his family during the holidays after Al's father loses his job.
