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As a first-time high school student, Chris (Tyler James Williams) 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 (guest star Jacqueline Mazarella), has placed him in the only all-white homeroom.

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Chris agrees to help a classmate, Angel improve his grades if Angel will help him get the attention of Chris' latest crush, Maria.

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Chris is thrilled when Jenise Huckstable asks him to the homecoming dance. His nerves begin to get the better of him when Jenise tells him that her father Dr. Clint Huckstable wants to meet him before the dance. Drew tries to get Doc to feng shui the store when he takes over Chris' hours.

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After Julius and Rochelle raise the rent, Mr. Omar demands reparations and moves in with the family while his apartment is being repaired. While there, he begins to play blackjack with Drew and Tonya using real money. Meanwhile, Chris is assigned to do a book report and decides to watch the movie instead of reading the book as an easy way out. However, as he later learns from Greg, the movie he saw did not match the book assigned.

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Although warned by Greg that it's a bad idea, Chris starts to help the football team with their homework as a means to socialize with the cool kids. As a result, Chris ends up failing his own exams. Meanwhile, Julius begins a new job collecting dead bodies for Mr. Omar's funeral home and soon finds himself appreciating life more. He begins to buy numerous gifts for his friends and relatives, but then ends up with financial troubles.

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Doc has a new girlfriend who is making life hard for Chris so he decides it's time to get her to move on. Rochelle is not happy when she finds a bra in Julius' sock draw, but what she doesn't know is that Tonya is the one that hid it there.

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Chris has a dilemma when a reward is offered for anyone who witnessed a shoot-out outside a movie theater. Chris was there but he was supposed to be babysitting Tonya and Drew - what will he do? Meanwhile, Julius and Rochelle have a very eventful anniversary at a Broadway musical.

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When the dorkiest girl in school, who everyone calls "Big Bird", asks Chris out on a date, he agrees but only to spare her feelings. He soon realizes after spending time with her that he genuinely likes her.

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Julius begins to take marriage advice from "The Oprah Winfrey Show" leading Rochelle to suspect an affair. Meanwhile, Chris volunteers for the "Big Brothers" program and is shocked when he learns the identity of is his "little brother".

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New Year's Eve in Times Square is something Chris really wants this year but needs an adult to accompany him. And that is where problems arise... Meanwhile, Tonya and Drew make a bet to see who stays up the longest and Julius becomes a local hero.