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.
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.
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.
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.
Don brings his two baby mamas together in hopes of uniting his family but Whitney has no intention of making nice. Ryan celebrates his 30th birthday in style with a Great Gatsby themed bash, but the celebration comes to a halt when Van confronts Cobra about her behavior. And Danielle’s boyfriend Terrence makes a fool of himself when his jealousy gets the best of him.
The crew heads to New Orleans for some Bourbon Street debauchery. Charmaine’s family demands that the she moves back home when they find out she’s broke. Don is caught off guard when his baby mama Whitney ambushes him at 9Mag. Van reaches his boiling point after Cobra confronts the crew about the cleanliness of the shop.
Van returns to work at 9 Mag but is angered that the shop has changed as 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.
Don’s paternity test results send him on a downward spiral as 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.
The shop is up in arms after Ryan hires a new tattoo artist. Fists fly when Kat learns that Charmaine threw her personal items in the trash. Don takes a paternity test hoping to squash the rumors that he fathered a love child. Van is finally released from boot camp but rising tensions in the shop could put a damper on his happy homecoming.
Ryan steps up his boss game when he learns that his staff is taking advantage of him. Kat betrays 9 Mag in order to take her Kat Tat brand to the next level. Don’s old college fling claims that he’s the father of her child, threatening his engagement to Ashley. Meanwhile, when the crew turns up for the biggest performance of Phor’s career, all hell breaks loose.
