Calvin and Jen have dinner with David and Dana Kang (Kipp Shiotani, Lauren Tom), who are constantly cursing at each other in public. Michael Kang (Yun Choi) breaks up with Terri, while Isaac begins seeing Michael's sister Michelle (Camille Chen). Eddie picks up a gorgeous woman (Sheryl Lee Ralph) in a bar.

Yinka tries new dirty talk on Jen's gynecologist (Victoria Platt). Jen competes with her sister Jan to find the perfect gift for Calvin's birthday. Terri finds marijuana in Romadal's locker, after which Issac, Yinka and Eddie join her in smoking it while on the job. The Kang siblings try to hide their flings with Terri and Isaac from their mother Dana. Jimmy decides to run for alderman. Eddie discovers that Claire is a transsexual.

Calvin learns that his mother and brother (Roz Ryan, Phil LaMarr) have known about his father's second family for years. The former mayor of Chicago (John Rubinstein) decides to run against Jimmy. After discovering Terri and Yinka's drug habits, Calvin forces them to enter drug rehab, led by an extremely confrontational drug counselor (Kevin Hart). Eddie's friends question his "deviant behavior" with Claire. Jen and Dana decide to open an urban bed and breakfast. Malcolm (A. Doran Reed) sues Calvin for invasion of privacy after he is caught on the surveillance cameras having sex in the back of the barbershop.

Calvin continues to spend time with his other family, and the barbershop suffers in his absence. Isaac steals a famous client from Yinka, and the two barbers eventually come to blows. A ventroliquist and his dummy cause trouble for Jen and Dana at the bed and breakfast. Yinka falls in love with a married Nigerian woman (Nzinga Blake). Romadal is arrested for assault.