Chicago Party Aunt Diane is an idolized troublemaker with a talent for avoiding adulthood — and a soft spot for her soul-searching nephew.
After one late night too many, Diane worries she’s out of step with the times but vows to school her nephew in living life.
Diane studies for a corporate test while Daniel moves in with her and begins job hunting, leading to some unfortunate encounters with city wildlife.
An unwanted senior citizen discount at Ribfest sends Diane on a quest to reassert her youth that runs into just one problem: she's getting older.
Diane and Bonnie's parents, Big Lou and Peg, fly in to tailgate at a Bears-Packers game, where a longstanding feud between rival families is reignited.
Hoping to score his first kiss, Daniel suits up for the Halloween costume party at Roscoe's Tavern, where Diane blabs a big secret about Gideon.
Mark overhears Bonnie saying he won't go the distance in the Chicago Marathon. Daniel is delayed in meeting the CEO of Kreativ Jus at the finish line.
Diane is thrilled to see the '85 Bears re-create the Super Bowl Shuffle at the Beefy Awards, but her son, Mikey, plans a dinner party for the same night.
On Christmas Eve, everyone has plans that don't involve Diane — until a glitchy voicemail has her panicked family searching hospitals to find her.
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 must wear a court-ordered breathalyzer bracelet, but it jeopardizes her living out one of her biggest dreams. Daniel's boss loses control.
Diane uses a dating app and matches with someone she least expected. Daniel starts seeing a professional baseball player for the Chicago Cubs.
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 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 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 partners with Gideon to sell homemade lotion but its secret ingredient proves costly. Bonnie wants to return to work as an event planner.
Gideon wants to take their lotion global, but Diane has second thoughts. Mark and Bonnie have financial trouble and may need to sell the condo.
