E1 - Chicago Party Aunt

Aired: September 17, 2021

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.

E2 - Helicopter Aunt

Aired: September 17, 2021

Diane studies for a corporate test while Daniel moves in with her and begins job hunting, leading to some unfortunate encounters with city wildlife.

E3 - Ribs for Her Pleasure

Aired: September 17, 2021

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.

E4 - Tailgate Jailgate

Aired: September 17, 2021

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.

E5 - Halloweener Circle

Aired: September 17, 2021

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.

E6 - Twenty-Six Point Tattoo

Aired: September 17, 2021

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.

E7 - The Beefys

Aired: September 17, 2021

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.

E8 - Emergency Contact

Aired: September 17, 2021

On Christmas Eve, everyone has plans that don't involve Diane — until a glitchy voicemail has her panicked family searching hospitals to find her.

E9 - Doppel Änger

Aired: December 30, 2022

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.

E10 - St. Patrick's Day

Aired: December 30, 2022

Diane must wear a court-ordered breathalyzer bracelet, but it jeopardizes her living out one of her biggest dreams. Daniel's boss loses control.

E11 - Go Scratch

Aired: December 30, 2022

Diane uses a dating app and matches with someone she least expected. Daniel starts seeing a professional baseball player for the Chicago Cubs.

E12 - Swing and a Ms.

Aired: December 30, 2022

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.

E13 - Empire State of Mind

Aired: December 30, 2022

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.

E14 - Tits Up, Tits Out

Aired: December 30, 2022

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.

E15 - Breaking Balm

Aired: December 30, 2022

Diane partners with Gideon to sell homemade lotion but its secret ingredient proves costly. Bonnie wants to return to work as an event planner.

E16 - Lotion Commotion

Aired: December 30, 2022

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.