As a first-time high school student, Chris is really looking forward to attending a school with some diversity. Unfortunately, when he arrives at school, he discovers that the school's new principal, Ms. Morello has placed him in the only all-white homeroom. Meanwhile, Rochelle helps Tonya land a job at Vanessa's beauty salon, but the customers don't take kindly to Tonya's brutally honest comments about their looks.
Chris agrees to help a classmate, Angel, improve his grades if Angel will help him get the attention of Chris' latest crush, Maria. Rochelle reluctantly befriends an ex-con named Peaches who has moved back into the neighborhood, but her good deed backfires when Peaches won't leave her alone. Meanwhile, Mr. Omar goes out of town and leaves Tonya and Drew in charge of caring for his fish.
Chris is on cloud nine when a cute girl, Jenise Huckstable invites him to the Tattaglia Homecoming Dance. However, his nerves take a turn for the worse when Jenise tells him that her father, Dr. Clint Huckstable wants Chris to come over to the house to meet him before the dance. Meanwhile, with Chris busy working with the high school's football team, Drew takes over Chris' hours at Doc's store and convinces Doc to feng shui the store.
When Julius and Rochelle decide to raise Mr. Omar's rent, Mr. Omar demands they bring the apartment up to code and moves in with Chris's family until the repairs are done.
Chris realizes that by helping the school's star running back and his friends with homework he is allowed to hang out with the cool kids. Greg tries to make him see that it's a bad idea, but Chris is too happy with his new friends to realize the downside until he fails his own quarterly exam.
When Doc's obnoxious new girlfriend, Stacy, makes Chris' life a living hell, Chris decides it's about time he split up the happy couple. Meanwhile, Tonya starts wearing a bra to get the attention of the boys in her class, but Rochelle loses her mind when Tonya naively hides her bra in Julius' sock drawer and Rochelle finds it there.
Although he is supposed to be home watching Drew and Tonya, Chris sneaks out to go to the movies with his friends and witnesses a shoot-out outside the theater.
Chris is just starting to fit in at his new high school when he gets asked on a date by the dorkiest girl in school, Kelly whom everyone calls "Big Bird." Chris only agrees to go out with her because he doesn't want to hurt her feelings, but after spending some time together he realizes that he genuinely likes her.
Julius realizes that the key to keeping Rochelle happy in their marriage is getting advice from "The Oprah Winfrey Show." Unfortunately, the plan backfires when Rochelle equates Julius' new attitude with an extramarital affair. Chris volunteers for the "Big Brothers" program, but is surprised to learn who is assigned to him as his "little brother."