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.

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.

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.

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.

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

Dylan has a new track that he's sure will get some attention, but he needs a female vocalist for the hook and after using Rebecca for the part, he can't contain his jealousy when she starts getting more attention than him.

Myles joins Dylan in camping out overnight for a chance to appear in a music video and score new sneakers, but a series of mishaps threatens Dylan's ability to actually get the shoes.

When a valuable collectible that Rebecca and Charlie sneak into school is confiscated by the principal, Dylan must help his cousins pull off an elaborate heist to retrieve it before Myles realizes it's missing.

Rebecca wants to use her new scooter to make social media posts, and Dylan wants to use it in a rap video, but both need to hide it from their parents if they want to keep it.

Accidentally trapped in the garage with Myles, Dylan puts his street smarts to the test against Charlie's scout smarts to see who can find a way out.

Charlie is tempted to change his clean reputation when a group of school vandals invites him into their clique, forcing Dylan to try to change Charlie's mind; Rebecca and Bethany protest when they are not allowed on the football team.

Rebecca and Dylan, desperate to sneak out of the house, plot how to get past Viola, nicknamed "Alcatraz" because no one has ever escaped on her watch; Charlie prepares a report on a historical person who inspires him.

Dylan insists that baseball isn't another one of his fleeting interests, but when he decides he wants to quit after a few days, he has to hide it from the family; Rebecca struggles to choose something for her class time capsule.

Dylan and Charlie decorate the school for a Halloween party and discover that the creepy janitor might be keeping a spooky secret; Rebecca and Bethany can't agree on a two-person costume for trick-or-treating.

Dylan's popularity skyrockets when he engages in an online rap battle, but the pressure to settle the beef at school creates a new set of problems; Rebecca's upcoming solo at church spurs Yasmine and Viola to offer fashion advice.

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

Blamed for a classmate's prank, Dylan must decide whether to reveal the real culprit, or suffer the consequences for taking the fall; Charlie and Rebecca think the family is being evicted from their home.

Hoping to be a baller in his latest music video, Dylan secures a credit card and starts ordering everything he needs to look the part, but after getting Rebecca and Charlie on board, the kids learn that credit card debt has to be paid back.

The family tries to make Dylan's first Christmas away from home special, but goes overboard trying to recreate his favorite traditions; the kids panic when they realize they don't have gifts for their parents.

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.

When Lay Lay and Dylan get duped into buying fake designer clothing, they team up to track down the scammer.

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.

Faking being sick to stay home from school, Dylan and Charlie plan a day of fun, but Rebecca tries to expose their lie.

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.

Appointed hall monitor, Dylan finds the job more than he bargained for; with their parents working evenings, Rebecca and Charlie must prove they can hold down household responsibilities by themselves.

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 falling asleep in class due to staying up late for a family tradition with Myles, Dylan is forced into Saturday detention; the family deals with Viola's competitive nature on game day.

After Myles and Yasmine enforce a no-technology policy into place, Dylan, Rebecca and Charlie find themselves on a treasure hunt in order to retrieve their gadgets.

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.

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

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.

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.

When he's hired to perform his hit viral song for a commercial, Dylan's artistic integrity is tested; Charlie must give a school presentation on someone in his family tree.

Dylan and Rebecca unexpectedly play the role of magician's assistant, while determined to return a cash-filled lock box to its rightful owner.

Dylan confronts 'Dylon' -- a poor imitation of himself with whom Bethany is smitten; Myles tries to help Yasmine fix their patio.

Viola teaches Rebecca and Dylan a lesson in sabotage. Myles introduces the family to camping.

Charlie enlists Dylan to help run his campaign for school ambassador against their mutual enemy Ace.

While receiving tutoring from Bethany, Dylan's decision to cheat leads to sabotaging Bethany's class presentation.

Myles worries he's losing the bond with Charlie as Charlie develops new interests that don't include Myles. Dylan and Rebecca learn about the financial woes of running their own record label.

Charlie convinces Dylan to stand-in for him in this year's Mother-Son dance leading to surprising consequences.

It's Halloween, and the Wilsons take the holiday very seriously; Dylan must deal with his family dressed up for Halloween when the heads of a hot brand stop by to interview him as a potential spokesperson, but while trying to do so, he experiences a series of fright, horror and trauma.

Dylan tries to mend a rift between Rebecca and Bethany only to make matters worse.

Dylan tries to convince local street artists to create a mural featuring himself resulting in widespread chaos.

Dylan and Rebecca hatch up a plan to set Viola up on a date with the delivery man.

Dylan and Rebecca secure a guest spot on a popular hot-wing eating talk show to promote their new record label, but when they get embarrassed on live TV and become the laughingstock of the school, they turn to Charlie to help get them back on the show; Myles and Viola compete against each other to see who is the most "adventurous", even if it means getting a risky tattoo.

After Rebecca is chosen as a model for a hot clothing boutique, Dylan and Bethany will do anything to get her back; a reluctant Charlie decides to let Myles and Yasmine take care of his baby egg for his class project.

Deciding they aren't babies anymore, Dylan and Charlie turn their bedroom into a man cave... until they end up with a rodent problem; Rebecca helps Myles co-manage his fantasy basketball team, but the two soon find themselves at odds.

When Rebecca embarks on a mission to sell Fun Goo, Dylan accidentally ruins all of her products, causing sabotage to her master plan to leave for Houston for an academic championship. Now Dylan and Rebecca have to make a new batch of goo, but when Dylan notices something is up with Rebecca, he soon learns the real reason why; Charlie goes to drastic lengths to avoid being embarrassed when he decides to join Yasmine's Bible club to impress a girl.

Dylan and Charlie's holiday spirit comes to a halt when they are grounded and are trapped in a delivery van on Christmas Eve; Yasmine becomes the student after trying to teach Rebecca a lesson about gratitude.

In an epic sleepover showdown, the girls and boys engage in a fierce battle to claim dominance over the living room; Myles and Yasmine attempt to have an entire night of fun to themselves in the garage, until Viola crashes the party.

After Charlie's video of Dylan performing a dance goes viral, Dylan must recover his reputation at school; Myles and Yasmine use coupons to trick Rebecca into doing house chores, until Viola and Rebecca get the upper hand.

The day of Dylan and Rebecca's launch party for their label is finally here! However, after a venue Rebecca had planned ends up being taken, the duo must find a way to secure a new venue for their big event before it's too late; Charlie and Viola contribute on their part to the label by opening up a mini diner at the house.