The Bert Show — Vault: Love Lost And Found – MILF Update

Date: December 2, 2025
Host: Pionaire Podcasting
Main Cast: Bert (Host), multiple co-hosts, Justin (Caller), Anna “Milfi” (Caller)

Episode Overview

In this “Love Lost And Found” segment, the Bert Show catches up with Justin, a 22-year-old who previously made waves seeking to reconnect with Anna, a 45-year-old woman he met at a Halloween party. Listeners get a charming, candid update on what happened after the show successfully reunited them. This episode explores age gaps, missed romantic signals, and the sometimes bungling, always entertaining reality of real-life meet-cutes gone awry.

Key Discussion Points & Insights

1. How 'Love Lost And Found' Works

• [01:06] Co-host 1: Explains the segment: Listeners who hit it off with someone but failed to exchange contact info can reach out to the show to help reconnect and see if sparks fly or fizzle.
  • “You give us the description of where you met... We give it to our Bert Show listeners... and then if they do, we reconnect you.”

2. Justin and Anna’s Story Recap

• [01:29] Host (Bert): Recaps the original scenario: Justin, 22, met Anna, 45, at the Jackie Lantern party, felt an instant connection but lost her number.
• The unusual age gap, party atmosphere, and costumes helped Anna stand out, making it “a slam dunk” to track her down.
  • “It was a pretty easy target. I mean a 45 year old hanging out at Jackie Lantern...”

3. Justin’s “Love Rap” & His Side of the Story

• [02:25] Justin: Charms everyone with a funny, self-deprecating party rap recounting the night he met Anna.
  • “I forgot what her name was so I saved it as Hamburger. After the park I went to my car and ended up real mad because I was so drunk. I deleted her number and I needed it real bad.”
• He likens their age gap to Ashton Kutcher and Demi Moore, cementing his tongue-in-cheek approach.
  • “Now Bert may think of you as Anne of the Milfian Moor, but we all know I'm Ashton and you're my Demi Moore.” (03:19)

4. Did Anything Happen After the Reunion?

• Multiple co-hosts speculate about how far Anna and Justin went after their radio-fueled reunion, with banter about Kama Sutra and “limbering up.”
• [04:41] Justin: Clarifies what happened on their night out (“at a compound again”):
  • “We had a couple of drinks and danced around for a little bit. We had a really good time. She’s a really nice person, but I think all that’s there is pretty much just the friendship between us.”

5. Exploring the Age Gap & Romantic Chemistry

• [05:05] Justin: Realizes that Anna probably prefers someone her own age:
  • “I think she wants to date... a guy her own age, has his own house... I guess I was too young for her.”
• [06:16] Justin: Tells a slapstick story of how, after a bathroom break, he and Anna lost each other in the huge club and never reconnected that night.
  • “I went to the restroom and came back... I came out and then she was gone.”

6. Social Dynamics & Miscommunication

• The hosts poke fun, suggesting Anna is still wandering the club (“like those Alzheimer patients that get out of the home”), but Justin insists he was looking for her.
• [07:12] Justin: Admits to giving up and dancing with strangers, while continuing to exchange texts with Anna (“She kept text messaging me like, ‘Hey, I’m waiting on you. I’m here. Where you left me.’”).

7. Anna’s Perspective

• [11:02] Anna Milfi: Joins the conversation, confirming no hard feelings, but making clear it’s just friendship.
  • “We had a good time... It was fun. We were there with a bunch of girls... I thought maybe he ditched me, but that's all right.”
• [11:57] Anna Milfi: Confirms that there will be no follow-up date due to existing romantic interest elsewhere.
  • “Yeah, I don't think so. I'm good. Friendship. I mean, he’s a really nice guy and. But I’m dating somebody and I’m really interested in that person.”

8. Age and Interest Revisited

• The hosts tease Anna about what age would make Justin a viable candidate:
  • [13:43] Anna Milfi: “Well, if he wasn’t 22, I would be interested in him. He’s got a great personality.”
  • [13:55] Host: “30? Would 30 change things?”
    Anna Milfi: “Maybe 30.”
• [14:01] Justin: Jokes, “I have to call you back in eight years, I guess.”

9. Final Thoughts & Endorsements

• Anna gives Justin a complimentary send-off:
  • [14:20] Anna Milfi: “Whoever gets to go on a date with him or have a relationship with him is very lucky. So that's sweet.”

Notable Quotes & Memorable Moments

• [02:25] Justin’s Rap:
  “Walking through the Jack Hugh Lantern party at the compound, trying to talk to every female that came around…”
• [03:19] Justin: “I’m Ashton and you’re my Demi Moore.”
• [05:05] Justin: “I guess I was too young for her… we hung out pretty much for like two hours at compound... laughed and had a great time.”
• [13:19] Anna Milfi: “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.”
• [13:43] Anna Milfi: “If he wasn’t 22, I would be interested in him. He’s got a great personality.”
• [14:01] Justin: “I have to call you back in eight years, I guess.”

Timeline of Important Segments

| Timestamp | Segment | |-----------|--------------------------------------------------------------| | 01:06 | How ‘Love Lost And Found’ works | | 01:29 | Justin & Anna’s story recap | | 02:25 | Justin performs his love rap | | 03:22 | Anna Milfi reacts to the rap | | 04:41 | Justin’s date details: “just friends” | | 06:16 | The bathroom mishap—how they lost each other | | 07:35 | Co-host jokes about Anna still wandering the club | | 11:02 | Anna joins the update, confirms only friendship possible | | 13:43 | Anna on considering Justin if he were older (“maybe 30…”) | | 14:20 | Anna’s sweet endorsement of Justin |

Tone & Style

True to The Bert Show’s vibe, the segment is full of playful banter, joking speculation, and a raw, cheerful honesty about dating and missed connections. Both Justin and Anna come across as fun, self-deprecating, and genuinely kind, echoing the show’s friendly and inclusive approach to real-life romantic misadventures.

In Summary

This episode of The Bert Show’s “Love Lost And Found” delivers a warm and witty update on Justin’s quest to reconnect with Anna after an age-defying chance meeting. Although romance wasn’t in the cards, both walk away with a memorable story and mutual admiration, showing that sometimes friendship (with a few good laughs) is the real win.