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.

Jen and Dana get help from Big Tricky and Da Boot (Kia Joy Goodwin) in developing their urban bed and breakfast. Calvin neglects the barbershop while spending time with his "other" family (Tanya Roberts, Christopher "Kid" Reid, Kendra Smith). Malcolm drops the lawsuit after Romadal attacks him. Jimmy's campaign manager (Lalanya Masters) starts to question whether Jimmy can win the election. Terri and her drug counselor James Ricky begin a very odd sexual relationship.

After Romadal jumps bail, Calvin tries to track him down to avoid losing the barbershop. As Election Day approaches, Jimmy seeks an endorsement from Eddie, who was "like a son" to the late Chicago mayor Harold Washington. Isaac and Terri finally give in to their mutual attraction and consummate their relationship. Yinka learns that Vivian is not as innocent as he thought. Shocking turns of events leave both Jen and Jimmy in desperate need of cash.