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Diane must wear a court-ordered breathalyzer bracelet, but it jeopardizes her living out one of her biggest dreams. Daniel's boss loses control.
Diane seems to find a kindred soul in a new neighbor. Bonnie and Mark want to have a new baby, while Daniel is shocked while taking an art class.
Diane uses a dating app and matches with someone she least expected. Daniel starts seeing a professional baseball player for the Chicago Cubs.
Chicago Party Aunt Diane's undying love for the Windy City is on full display as she tries sobriety, dating and going into the lotion-making business.