It’s “Take Your Son to Work Day” and Dean heads to band practice with Bill. But the “grown folks’ business” at the music studio prompts Lillian to have to pick up Dean. While at her office, Dean finally learns what his mom does while he’s at school all day, gaining a newfound respect for her career and ambition.

Dean tries to impress Keisa's cool new boyfriend by inviting him and his friends to a party Kim is throwing while Bill and Lillian are away for the night; things get out of hand just as Bill and Lillian arrive home.

Torn between his secret relationship with Keisa and his friendship with Broderick, Dean turns to Jackie for advice. Meanwhile, after her latest run-in with the law, Jackie decides to turn over a new leaf.

After Lillian's boss announces budget cuts, she is forced to make a decision and enforce boundaries between her personal and professional life. Meanwhile, Dean and Cory's friendship hits a few speed bumps as they work together for the boxcar derby.