Chris and his family move to Bed-Stuy and Chris attends a predominantly white middle school where he meets his new friend, Greg and ends up in the crosshairs of the school bully, Joey Caruso.
Chris has a crush on Keisha, the girl next door and when Rochelle asks Keisha to help Drew with his math, Chris makes his move to impress her, but is heartbroken when he catches Drew kissing Keisha. Julius finds himself in an uncomfortable position when he suddenly becomes attracted to Keisha's mom, Sheila. Also, when the school principal orders Caruso to stay away from Chris, Greg sticks close to him.
The school basketball coach recruits Chris for the basketball team, but there's one problem: he doesn't know how to play. But a bad grade on a pop quiz could kick him off the team. Meanwhile, Rochelle has her suspicions about a new tenant in their building.
When Julius buys a big crate of sausage, he makes everyone eat it with every meal. But Tonya refuses to, causing friction between the her and Rochelle. While at school, Chris is sentenced to 3 days of detention after a rumor goes round about him beating up the school bully, Joey.
Despite his parents' warnings, Chris lends his bike to a kid who disappears with it; While Julius is on strike, he proves to be a better housekeeper than Rochelle which makes her very angry.
In order to impress a girl Chris goes to an adult party where the girl will be. With some urging from his friend he decides to go as the eccentric singer Prince.
When Rochelle and Julius go out for the night, they hire a sitter to look after Chris, Drew, and Tonya. But the babysitter keeps leaving the house and Chris covers for her. Julius and Rochelle's night-out is anything but romantic when the restaurant gets robbed.
Toyna keeps getting Chris into trouble and Chris is sick of it, so he decides to hang out at Greg's house without permission from either of their parents. When Greg's father comes home and Chris finds out Greg isn't allowed to have anyone over when his dad's not home, Chris hides in the closet to avoid getting into trouble.
Rochelle and Julius don't have enough money to get Chris his new Walkman that he wants for Christmas. Drew tells Toyna the truth about Santa Claus, which makes Tonya question about other things her mom and dad told her.
In order to get a new leather jacket, Chris goes to work with Julius. When Drew and Tonya's school is shut down because of lead paint poisoning, the two play a game of "I Dare You" which gets out of hand when Toyna ends up in the emergency room.
Chris gets a new outfit for school picture day, but Caruso ends up stealing it. Drew hides Toyna's shoe when she breaks his toy. Rochelle sells make-up at home to make some extra money.
Chris gets a bunch of "I hate you" cards from Caruso and also develops a crush on a girl named Tangee on his bus ride. Tonya reveals that she has a boyfriend which surprises Julius, and Drew gets a bunch of Valentines' cards from a lot of girls.
Julius and Rochelle struggle to give up the things they like: chocolate turtles and lottery tickets. Meanwhile, Chris claims to be a pro at "Asteroids", but when he hears that someone beat his score, it's up to him to defend his title.
Chris gets an "F" on his report card and tries to figure out a way to change his grade before his parents find out. When Julius is sick with the gout, he starts watching The Young and the Restless.
When Rochelle's dad, Gene unexpectedly dies during a family dinner, Rochelle starts acting less than normal and Chris is shocked to see his mother not acting like herself.
Fed up with Drew being the best at everything, Chris decides to take up karate. But when the two brothers challenge each other, Chris ends up breaking Drew's hand. Meanwhile, Toyna gets a lesson in gossip at the beauty salon.
Chris finds a Playboy magazine in Julius' toolbox and takes it to school, but the assistant principal confiscates it, Chris attempts to get it back. Julius is surprised when he finds out that Rochelle has money stashed in their room. Toyna teases Drew because of his fear of spiders.
Chris has to sell cookies in order to go on a field trip to Washington D.C. Meanwhile Julius and Rochelle had tickets for Dreamgirls but Drew and Tonya get sick.
