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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.
Diane uses a dating app and matches with someone she least expected. Daniel starts seeing a professional baseball player for the Chicago Cubs.
Diane tries to find a way to cheer Daniel up, but they then get into a big fight. Mark goes to stay with Diane after he and Bonnie argue.
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.