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Diane uses a dating app and matches with someone she least expected. Daniel starts seeing a professional baseball player for the Chicago Cubs.
Diane must wear a court-ordered breathalyzer bracelet, but it jeopardizes her living out one of her biggest dreams. Daniel's boss loses control.
Daniel doesn't want his Aunt Diane to know who he's dating because he fears what she may do. Diane tries dating a nice guy, for once.
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.