There was a special edition of Dumpster Fire Dating so Alley could fill everyone in on her date with Orphan Boy over the weekend. Did it get romantic or stay in the friend zone? DZ helps out a man who has saved a lot of money and doesn't know what to do with it. Ariana in West Allis asks if she's the jerk for going against her husband's wishes. Alley was traumatized by her experience in a parking garage and DZ and his family had major nostalgia after visiting a local fast food spot.

Dumpster Fire Dating was INSANE today because Orphan Boy actually had the courage to call into the show and discuss the status of his relationship with Alley. DZ helps out a woman whose neighbors are trying to ruin her Halloween display. The question of the day involves snacks you grab on the go after Alley taught her son about a legendary snack move. A woman shocks everyone on Am I the jerk when she asks her boyfriend to get a Halloween tattoo with her or else the relationship will end. Happy Halloween!

Is it better to be single or taken? That's the question of the day and everyone shares their own pros and cons. It turns out we think negatively about our body 4 times a day so Alley and DZ decide to try and tackle this problem. DZ helps out a woman who is going back to school full time but needs ideas finding a job that fits her new schedule. Is she a jerk for not giving a ride to her coworker whose car broke down? It was not a clean sweep today on Am I the Jerk. Alley is excited to be an aunt in real life even though she's had neices and nephews for years.

She has a coworker with a broken down car, but she really likes her alone time. Is she the jerk for not giving her coworker a ride?

Halloween is the loneliest holiday for singles and Alley explains why today. Her son gives his hilarious trick or treating recap(what candy did Hudson truly appreciate??). You won’t believe what the most popular sandwich is and that turns into the question of the day. A man needs help from DZ because he hates the couple costume his girl picked out. Clarice asks if she’s the jerk for not congratulating her newly married brother in law. DZ explains why he can’t go to physical therapy anymore for his knee and they discuss all the ways to make daylight saving easier on you this weekend. Enjoy the show!

Alley and DZ went out to dinner with their families over the weekend and Alley finds out DZ slipped something to her kids when she wasn’t looking. There are two new celebrity couples that no one saw coming. DZ helps out someone who wants their roommate to stop getting busy while they are home. A man asks if he’s the jerk for not hiring his friend’s kid. DZ is struggling with his kids' sleeping arrangements, so everyone shares advice on how to make more space when kids share a bedroom.