Dylan writes a serious rap about his mom, prompting Martin to read his diary to find out if he’s doing ok. Dylan catches him in the act, triggering an escalating run of each family member invading the others’ privacy.

Yasmine’s celebrity client DJ Khaled visits, presenting Dylan with a golden opportunity to prove his rap credentials and score a record deal.

On his first day at school, Dylan starts a classroom protest over having to wear uniforms.

Rebecca is being bullied online, prompting Dylan to encourage Martin to respond to some of the posts. His posts are not anonymous, however, and the family must deal with the fallout.

The kids help Myles plan Yasmine’s big dinner at the house for her boss. While Myles struggles to write a speech in honor of his wife, the kids throw out the catered food and plan their own menu.

Charlie seeks Dylan's help when he has a crush on a girl, but Dylan's rap music-informed advice clashes with Rebecca's more feminist take on how Charlie should handle the situation.

After failing to get approval to go to the school dance, Rebecca tells her date that she can’t go because her grandmother has died, a lie that leads to a series of misunderstandings within the family.

Dylan doesn’t want to attend school, and does whatever it takes to avoid going, including convincing little Charlie not to go, either.

The family can't get any peace while Dylan plays the drums all day and night, and everyone tries to convince him that he needs to give up his new instrument for good.

Rebecca is babysitting Charlie and Dylan, but when a deliveryman arrives with a package from Dylan’s mom, Rebecca and Dylan fight over the rule about not opening the door.

Young Dylan arrives at his relatives' home needing a place to live, but his streetwise swagger upends the conservative Wilson household.

Dylan has trouble adjusting to the Wilson family’s rules, leading to confrontation with his uncle that makes him feel unwanted.

Dylan tries to help Charlie with his homework, but his unconventional style of doing his homework comes to a head with Dylan gets into a rap battle with their teacher.

A lucky guess in math class lands Dylan on the Mathlete squad, where his teammate, Rebecca, is worried that he will hurt their chances in the upcoming regional competition.

When the school does a hip-hop version of Shakespeare, Dylan takes on another boy for the lead role; after only being cast as an understudy, Dylan is determined to outshine his rival and nab the part for himself.

Dylan gets ready to return to Chicago with his mother when a change in the plan causes him to question their relationship and prompts the Wilson family to help him through this latest crisis.

When Dylan is assigned to write a history report for school, he travels back in time to the Harlem Renaissance.

Charlie's habit of listening to other people's private conversations goes wrong after he informs Yasmine and Miles of Dylan's new life plan; Rebecca learns the meaning for true friendship and accepting oneself.

Dylan plays detective after an expensive vase is broken in the house, but no one admits guilt, and everyone is a suspect.

Rebecca's assignment to study animals in the wild leads her to observe Dylan and Charlie as they battle for suprema

Dylan discovers his new substitute teacher is a former rap star, and Dylan plots to get him back on top; after successfully reviving the former star's profile, Dylan finds that own dream remains out of reach.

With the annual Juneteenth parade on the horizon, Dylan and Rebecca find themselves at odds over the float parade; Myles and Yasmine utilize Charlie's culinary skills to bake pies for Viola's church social.

Dylan becomes an egomaniac when he thinks his latest song is a number one hit in Nigeria; Yasmine enlists Rebecca to direct a commercial for her business.

After secretly opening his birthday gift from Myles and Yasmine early, Dylan must invent a cover up when he accidentally destroys it; the family plans to be the top seller at the neighborhood yard sale by way of Charlie's culinary skills.

Dylan and Rebecca form an unlikely team to win a school gaming competition; Charlie is tasked with painting a portrait of Myles and Yasmine.

After his old rap group from Chicago pays him a visit, Dylan must decide between the past and his future as a solo artist; Rebecca puts Myles and Yasmine on a strict diet regimen.

Dylan and Charlie cause chaos among the family in an attempt to create a dramatic audition tape for a reality TV show; Rebecca and Bethany teach Dylan a lesson about compromising his values.

As the school dance approaches, Dylan and Tara work together after they realize they have the same nefarious hidden agenda; Yasmine becomes overly protective of Charlie when the family supports his decorating efforts.

Viola and Dylan work on his de-stressing skills so that he can reconnect with his rapping abilities; Yasmine reluctantly seeks help from Charlie for her anniversary plans.

Rebecca offers anonymous advice to her peers and a superior but goes further than is appropriate; Myles and Yasmine struggle to be partners until Charlie leads them with his advice.

Dylan must make amends after he invades the privacy and violates the trust of a classmate; Yasmine and Myles are disappointed when Charlie uncovers an awful truth.

Charlie gets his first job but must stand up for himself in order to keep it; Rebecca realizes that Tracee may be more manipulative than she appears.