E1.
Food for the SoulDylan 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.
E2.
My Fair CharlieCharlie 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.
E3.
A Tale of Two RappersWhen 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.
E4.
EinsteinsA 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.
E5.
Who Done Done It?Dylan plays detective after an expensive vase is broken in the house, but no one admits guilt, and everyone is a suspect.