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After 2nd City Ink's Zach brokers a deal with Draya in exchange for a date, they flirt with the idea of starting a shop romance. Ryan opens up about some family issues in therapy.
Charmaine bounces back with a shop of her own, with London's hottest black female tattoo artist by her side. Ryan's business excels as his personal life struggles. Don and Ashley get unexpected news.
Charmaine announces her pregnancy to the 2nd City crew and tries to appease her unhappy mother-in-law. Jess announces a pajama party at her house and gets a dose of reality of Chicago life with Prince and Fly.