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Diane wins a free mammogram and needs to see a specialist after the results, so Bonnie helps out. Daniel tries to overcome his anxiety over driving.
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.
Diane partners with Gideon to sell homemade lotion but its secret ingredient proves costly. Bonnie wants to return to work as an event planner.
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.