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A new pint size personality joins the show and Alley and DZ let her join in for Am I the Jerk. DZ is celebrating his wedding anniversary and his wife left a voice message for him. Alley is still at war with her sons over the lunch money. DZ gives advice to someone who wants to leave their job but doesn't want to break a commitment. DZ gives an update on the broken couch.

She knows he's the one, but she still needs him to change his number. Is she the jerk?

DZ is at a loss on what to do with his son moving forward and needs advice. Alley confronts her son about trying to take advantage of her and his response is funny. Is it a jerk move to yell at someone who is smoking in the car with kids? That's the moral dilemma one woman has. DZ's kids broke his couch and he is trying to figure out if he should fix it or cave and buy a new one.

She was triggered when she saw a man smoking with his kids in the car and she said something. Is she a jerk?

Alley and DZ invite their coworker in to share the therapy she tried, that ended up helping her cope with serious trauma that stemmed from a family death. DZ shares his time at Bucks media day. They discuss the best Halloween candy and you might be suprised which one tops the list this year. DZ gives advice to someone who has a smelly coworker. Is she the jerk for turning down a free service from her friend?

She was offered a free service from her friend, but turned it down. Is she the jerk?

Alley’s dog Doug almost died this weekend at the More Than Pink walk. DZ’s son calls him out for having the worst favorite color. A woman asks if she’s the jerk for screaming WOOHOO when the singer asks “where are all the single ladies at?!” at a concert she attended with her husband. DZ gets an email about someone’s ex fiance keeping their stuff after the breakup so he moves it right to the top on What Would DZ Do. What Milwaukee suburb is giving away free Ring cams?

She got really excited at the concert and now her husband is mad. Is she the jerk?

Doug's Diaries returns and Doug met a new family member this week. DZ got his son's school pics back which had everyone feeling nostalgia. Did your parents order pics? A woman asks if she's the jerk after she cheated on her boyfriend. Alley is getting ready to help a local high school with homecoming. DZ gives advice to someone who dated a coworker and doesn't know how to proceed. Ed the IT guy suprises everyone with his mom, live in person from Boston, and everyone couldn't stop listening to the stories she had.

She cheated and now everyone is mad at her. Is she the jerk?

She used a pic that was VERY old but doesn't care. Is she the jerk?

Alley found out her kids were playing her the whole time. DZ is at a loss on what to do about his sons school bus route. The owner of local store All Goods joins the show for Hispanic Heritage Month and he shares his love for the city and why he opened his store. Is it a jerk move to not wish someone a happy birthday? DZ gives advice to someone who isn't sure how to get their girlfriend to stop being a know it all.

He doesn't even remember when her birthday is. Is he a jerk?

Alley is tired of her kids texting her about money, even though she was excited about the reason. DZ checked out his first apple orchard of the season. A man asks if he's the jerk for taunting his wife while she drives. Someone lost money in Milwaukee and posted on social media trying to find it. That led to the question of the day. DZ gives advice to someone who isn't sure if they should partake in the work drama or leave it alone.