When Dre takes over "mom'' duties, the praise he gets from everyone at the school goes to his head.

Pops comes to the rescue with the colorful story of how his great-great grandfather, Drexler Johnson, bet the future of the Johnson family against a ruthless gangster, Elroy Savoy, for Jack and Diane's school assignment.

Jack performs the song “Gold Digger” at a school talent show and when he sings a lyric that includes THE word, it leads to his possible expulsion from school. Dre and Bow work together to get him reinstated, and along the way, examine the evolution of THE word through the generations and just who, if anyone, has the right to use it.

The Johnsons go to Jack and Diane’s school play about Columbus Day, and Dre is dismayed by the historically inaccurate way that the holiday is portrayed. He feels like there aren’t enough black holidays, so he enlists Aloe Blacc at work to help him create a catchy song to raise awareness for a holiday worth celebrating, Juneteenth.

Diane experiences a big life event toward becoming a woman and Bow, Ruby, Zoey and Alicia are there to support her. Meanwhile, afraid that he may never be able to beat Junior at basketball again, Dre conducts psychological warfare on Junior before challenging him to a game.

Bow keeps in touch with Dre’s incarcerated godbrother, Omar, but when they find out he is being released from prison, Omar’s future sparks debate. Meanwhile, Ruby lets it slip to the kids that she’s been to jail and they push her to tell them more secrets from her past.

Bow struggles to adjust as she returns to work after maternity leave. Meanwhile, Ruby gives the twins a “workaround” plan to get out of doing homework.

Dre and Bow struggle with the changing times of identity politics and gender neutrality. Diane auditions for the school play and scores the male lead part, but her crush starts spending time with another girl. Meanwhile, Junior’s Valentine’s Day date goes awry after Dre and Pops have a talk with him about chivalry.

Dre is upset after he learns that Jack and Diane are getting the same surface-level education about Black History Month that he got when he was growing up. After taking it up with the twins’ teacher, he is asked to present at the assembly and wants to bring Black history to life.

Jack joins the robotics club and Dre worries it might be a detrimental failure for him after already being cut from the basketball team. Ruby embellishes a story for Diane’s school project.