City Guys - Season 2 (1998)

After being robbed at gunpoint one night, 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. However, 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 to his own days of bullying people, and even begins to isolate his friends. But when Miss Noble gets a hold 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, 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 Ms. 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 granted one too many times. 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.