Jen convinces Calvin to hire her distant relative Romadal Dupree, who has just been released from prison. Calvin teaches Yinka how to talk dirty to a woman during sex. Terri is forced to confront her anger issues after her identity is stolen. Jimmy tries to use his nonexistent political clout to do a favor for Jen.
"Niggaz", an urban fashion chain store owned by African-Americans, opens a franchise in the neighborhood. But when the owner of the new store turns out to be Korean-American, some residents are outraged by the use of the N-word . . . and Jimmy takes full advantage of the situation. Terri is attracted to the son of the new store owner. Big Tricky (Page Kennedy) wants his cousin Romadal to be the spokesman for his new hip-hop CD, but he needs Calvin's approval first.
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.
The barbershop staff (along with Jen and Jimmy) attends one of Bill Cosby's lectures on personal responsibility in the African-American community. Terri and Yinka continue to smoke marijuana at the barbershop, which drastically affects their work performance. Isaac, who only dates women of color, decides to try dating White women. Eddie is in turmoil after learning the truth about Claire. Calvin learns that his late father had a second family . . . including a White wife and adult biracial children.
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.
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.
When Isaac puts his celebrity clientele ahead of his regular job, Calvin fires him. Jimmy tries to raise funds and support for his faltering campaign. Calvin puts up the barbershop as collateral to bail Romadal out of jail . . . but then Romadal disappears. After learning that Vivian will be put to death upon her return to Nigeria, Yinka helps her seek sanctuary at the bed and breakfast.
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.