Ryan learns that his staff is taking advantage of him; Kat betrays 9 Mag in order to take her brand to the next level; Don's former college fling claims that he is the father of her child.
Ryan hires a tattoo artist; Kat learns that Charmaine threw away her personal items; Don takes a paternity test; Van is released from boot camp.
Don’s paternity test results send him on a downward spiral. Ryan dips his toes back in the dating pool. Van has an emotional reunion with his daughter after being separated from her for four months. Danielle’s birthday celebration turns into chaos when Ashley and her friends crash the party and attack Charmaine.
Van returns to work at 9 Mag but is angered that the shop has changed. Charmaine is forced to face the consequences of quitting her corporate job and following her dreams. Ashley confronts Don about fathering another child with another woman. Tempers flare when Ryan introduces yet another new tattoo artist in the shop.
The crew travels to New Orleans; Charmaine's family insist that she moves home; Whitney ambushes Don; Cobra confronts the crew.
Don attempts to unite his family; Ryan celebrates his 30th birthday; Van confronts Cobra about her behavior.
Don receives some life-shattering news that could send him back into a spiral. Charmaine is determined to improve her financial situation and auditions to be a radio DJ. In the wake of one of the deadliest weekends in Chicago history, Phor heads into the studio with one of hip hop’s top rappers to record a song about peace. When Cobra’s behavior becomes questionable, Ryan is forced to make a tough decision about her future at 9 Mag.
With his jail sentence looming, Don pushes up his wedding date. Kat hosts her first art show, but things turn sour when Phor shows up with the woman he cheated on Kat with. Van’s relationship is tested after he confesses to his girlfriend that he’s not a one-woman kind of guy. Phor’s girlfriend Nikki confronts Kat about her attitude at a 9 Mag party—and things get physical.
The 9 Mag crew heads to the Dominican Republic for Don’s wedding. Kat confronts Phor about cheating on her when they were together. Van’s threesome goes horribly wrong when his girlfriend brings a surprise guest to share in on the fun. And Don gets a little too friendly with a stripper, jeopardizing his wedding to Ashley.
In the Season 2 finale, Ashley arrives in the Dominican Republic for her wedding and asks her brother to spy on Don's bachelor party. Later, Terrence gives Danielle an ultimatum; and Ashley threatens to call off the big day after seeing risqué pictures from the bachelor party.