The Bert Show – Full Show PT 2: Tuesday, December 2 [Vault]

Date: December 2, 2025
Host: Matt Rogers (with co-hosts Jeff, Jen Hobby, Bowen Yang, and guest participants)
Episode Context & Theme
Key Segments & Discussion Points
Notable Quotes & Memorable Moments
Timestamps

Episode Overview

This episode of The Bert Show continues their trademark mix of real-life escapades, relationship drama, and hilarious banter. The main focus is twofold:

• Listener follow-up stories from “Love Lost and Found Again”: A segment where people reconnect with lost romantic interests with the help of show listeners—and, sometimes, the cast acts as reality check referees.
• Revenge Tales: Listeners call in to share notorious (and occasionally deranged) “payback” stories after being wronged in relationships, creating a blend of confession, outrage, and collective comic relief.

The tone is playful, candid, and a bit mischievous, spotlighting authentic, sometimes cringey, human moments.

Key Discussion Points

1. “Love Lost and Found Again”: Justin & Anna Milfi Update

[01:00-14:32]

• Recap of Justin and Anna’s Story:

  • Justin, 22, met Anna (“Anna Milfi”), 45, at a Jack O’ Lantern Halloween party.
  • He was smitten, but after drunkenly saving her number as “hamburger” in his phone, he lost it. The show previously helped him find Anna.

• Their Weekend Meet-Up:

  • The long-awaited hangout at Compound didn’t quite pan out romantically:
    • Drinks, dancing, and laughs
    • Both report they “lost” each other during the night (conflict over whether anyone was ditched or just caught up in the club chaos)
    • They remain friends, but Anna is dating someone her own age and isn’t interested in more (despite finding Justin sweet and mature).

• Age Gaps, Flirtation, and Friend Zoning:

  • The age difference is a recurring, light-hearted gag.
  • Both Justin and Anna are gracious; Anna admits she’s flattered but not interested in dating someone her son’s age. Justin takes it in stride, joking about the “cougar” friendship.

2. Revenge Stories: What We Do When Wronged

[16:21-27:17]

A. Confessions of Relationship Fury

Listeners call in with epic tales of revenge after discovering infidelity or betrayal. Stories range from destructive to cunning:

• Anna Milfi’s “Waiting to Exhale” Moment [16:33-17:14]

  • Caught partner cheating, responded by burning her clothes in the basement. Realized she could’ve burned down the house, which prompts “yikes!” laughs from the cast.

• Christina’s Scorched-Earth Breakup [17:53-19:36]

  • After being cheated on, Christina destroys her ex’s clothing, bleaches his shoes, and tosses his possessions into a lake—admitting postpartum depression amplified her rage.

• Nicole, the “Silent Devil” [20:02-21:47]

  • Secretly “cleans” an ex’s toothbrush in the toilet and hides a piece of shrimp under the carpet to create an untraceable stink after a breakup.

B. On-Air “Public Service Announcement” Revenge [23:38-24:57]

• A caller outs her cheating boyfriend Ethan live on air:
  • Exposes his infidelity, married lover (name and all), and graphic evidence.
  • Threatens to send all incriminating emails (and vacation photos) to his coworkers and the lover’s husband, Raj.
  • Cast is scandalized/fascinated; emphasizes that the original broadcast did not bleep out names, causing workplace drama.

C. Another Dramatic Destruction Story [25:41-26:55]

• Angela’s Bricks and Cement Mayhem
  • After learning her partner was taking their son to the other woman’s house, Angela attacked his new car with bricks and poured cement in the engine.

Notable Quotes & Moments

The Justin & Anna Saga

• Justin’s Lovesick Rap (02:23):

  “Walking through the Jack Hugh Lantern party at the compound...dressed as a gay cowboy from Brokeback Mountain... I forgot what her name was so I saved it as hamburger... Q100 saved the day and helped me find my match... Bert may think of you as Anna the Milfy and more, but we all know I’m Ashton and you’re my Demi Moore.” — Justin ([02:23])

• On Why It Didn’t Work:

  "We had a really good time...but all that's there is pretty much just the friendship between us."
  — Justin ([04:43])

  "I think she wants to date, you know, a guy her own age, you know, has his own house and all that stuff...I guess I was too young for her."
  — Justin ([05:04])

• Anna’s Perspective:

  "It was a little embarrassing at first because I thought, you know, I’m too old for...as old as my son. But it is a compliment."
  — Anna Milfi ([13:18])

  "If he was 25, would that change things?"
  "I don't think so."
  — Matt Rogers & Anna Milfi ([13:46-13:49])

Revenge Tales

• The Clothes-Pyro:

  "Went to the basement, cut them up, took lighter fluid, put them on them and lit them all on fire."
  — Anna Milfi ([17:08])

  "It's a Waiting to Exhale moment."
  — Co-host Jeff ([17:14])

• Lake and Bleach Vengeance:

  "He had a lot of Timberland boots, a lot of stuff that this chick had bought him. I made sure I bleached them right...his dad lived by, like, a lake, I just threw some of the stuff in the lake."
  — Christina ([18:23])

• The Shrimp Under the Carpet:

  "I cut a hole in the carpet and I put a piece of shrimp underneath the carpet."
  — Nicole ([21:01])

• On Revenge Creativity:

  “That is awesome. You know, somebody listening right now just went like, that’s it.”
  — Jen Hobby ([21:20])

• Public Service Outing:

  "Ethan shouldn’t leave his laptop up and running on the kitchen table when his girlfriend spends the night…as soon as she gets home, she could email all of those to all of your coworkers…to the whore named Sarah who is married...I’m going to call you and tell you everything…"
  — Caller ([23:38-24:57])

• Ruinous Destruction with Bricks:

  "Took all the bricks, threw in the car and completely ruined the car and had to come tow it...open up the hood, you know, threw bricks in the sand, cement into the engine..."
  — Angela ([26:03-26:49])

Important Segments and Timestamps

• [01:00] Love Lost & Found Again – Justin & Anna Recap
• [02:23] Justin’s Halloween Party Rap for Anna
• [04:43-07:08] Justin & Anna Reunite, But Only as Friends
• [11:00] Anna Joins the Conversation, Friendzones Justin
• [13:41] Discussion: Would Age Actually Change Anything?
• [16:21] Revenge Story Hour — Call-ins Begin
• [17:14] Burning Clothes Revenge
• [18:23] Lake & Bleach: Christina’s Meltdown
• [21:01] Shrimp Under Carpet & Other Ingenious Vengeance
• [23:38] Live On-Air Revenge “Public Service Announcement”
• [25:41] Angela’s Car Destruction With Bricks & Cement

Conclusion

This episode showcases the humorous, sometimes jaw-dropping extremes people go to after romantic letdowns—whether trying to recapture lost love or get even after betrayal. The cast keeps it funny, compassionate, and at times gleefully scandalized, allowing listeners to both laugh and empathize.

Why Listen?
For the pure entertainment of real-life messiness, shameless confessions, and the camaraderie of a morning show that never takes itself too seriously.

Cast Attribution:

• Matt Rogers — Host, main interviewer
• Jeff, Jen Hobby, Bowen Yang — Co-hosts, banter and commentary
• Justin, Anna Milfi, Christina, Nicole, Angela — Callers and story subjects

Skip the intros/outros—dive right into the human drama!