Messing With The Mailman Episode — The Middle Classholes

The tables have officially turned! In this episode, Murray gets a taste of his own medicine when a group of kids on e-bikes decide to harass him while he’s out on his delivery route. Faced with teens pulling dangerous bike tricks in front of his 1980s mail truck, Murr reaches a classic midlife realization: he has officially become the grumpy adult he used to mess with back in the day.

The guys swap stories of childhood delinquency—including Wes’s late-night fireworks, construction site destruction, and terrorizing the local newspaper delivery man while wearing a terrifying, custom-made porcelain devil mask.

Later in the episode, the crew dives into a BuzzFeed list highlighting things that have become "socially acceptable" in the last ten years. They debate everything from location sharing among friends and last-minute plan cancellations to using AI as a therapist and the breakdown of proper dress codes.

Finally, Murray rounds out the show with Fun Fact Friday, featuring public servant blunders—including a mayor taking bribes on a yacht from "vetted" undercover FBI agents and a politician caught red-handed stealing sunglasses at an airport.

00:15 — The Shoe Has Flipped
03:45 — Murray’s E-Bike Standoff on the Mail Route
09:30 — Realizing You’ve Become the Grumpy Adult
14:15 — Wes’s Childhood Shenanigans & The Devil Mask
21:00 — Socially Acceptable Now: Location Sharing & Tracking
27:30 — Canceling Plans: "Protecting Your Peace" or Flaking?
34:15 — Phone Etiquette, Dress Codes, and AI Therapy
41:00 — Fun Fact Friday: Public Servant Blunders
46:30 — Corruption on a Yacht & Airport Sunglasses Theft
52:15 — Final Thoughts & Episode Wrap-Up