Vault: Love Lost And Found - MILF Update

Summary

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)

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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.

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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.”

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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.”

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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 |

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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.

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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.

Transcript

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[Host (possibly Bert)]

The Birch show all right, Melissa. How does Love Lost and found again work? Very quickly.

[Co-host 1]

Here it is where someone is out and you find a connection with somebody and then you get kind of nervous because you know, toward the end you, you don't know what you're going to say when you have to part ways and then you don't get the phone number. You have no way of contacting the person. You think you've lost them forever. So you give us a call and then you give us the description of where you met, what they look like, everything about them. We give it to our Burt show listeners to see if anybody out there knows them and then if they do, we reconnect you.

[Host (possibly Bert)]

Such is the case with 22 year old Justin who went to Love Lost and or who went to Jackie Lantern and ended up like really digging this 45 year old Anna Milfi that was there totally digging on her.

[Co-host 2]

He thought they really had a connection. It wasn't just that she was hot. I mean that was definitely helping deep connect. But he felt like they really had some, you know, maybe not a deep connection but some chemistry going on. And he was like, I don't care. I think that she's hot. I don't care about the age difference. I want this woman.

[Host (possibly Bert)]

So he goes in to put her number in his cell phone and somehow screws it up. Because he's all hammered and stuff and he comes on with us to try to find her and we did. And it was a pretty easy target. I mean a 45 year old hanging out at Jackie Lantern and was a pretty easy target.

[Co-host 3]

So we plus any Jack O Lantern one too. Like because of the costumes and everything, it's easy to narrow down. Like this is a sure thing for him.

[Host (possibly Bert)]

This was a slam dunk here.

[Co-host 3]

I mean he had no doubt. That's when he put the pen to paper.

[Justin]

Walking through the Jack Hugh Lantern party at the compound, trying to talk to every female that came around. So I'm chilling at the party, posted by the water fountain, dressed as a gay cowboy from Brokeback Mountain, looking all around and I saw from an angle a nice looking woman in her costume read Fallen Angel. I asked for her number even though it was kind of risky and if she said no, I would just have said I was tipsy. We split our different ways to enjoy the party further, but 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. I felt ashamed and so out of place like an apple in a pumpkin patch. Till Q100 saved the day and helped me find my match. 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.

[Anna Milfi]

That was fabulous.

[Justin]

And here's the last part. And if it doesn't work out between us, I'll be sad, but what the heck, I'll introduce you to my dad.

[Host (possibly Bert)]

I still think it was great. I still think it was great. It was effort.

[Verizon Announcer]

A for effort.

[Co-host 1]

Yes.

[Co-host 3]

And that's all the. All the women want, right?

[Co-host 2]

I just think that he should have ended it on the Demi Moore line. That was cute.

[Justin]

Hey, Justin, what's going on?

[Host (possibly Bert)]

Dude, you're not calling us from a bathroom, are you?

[Justin]

No, no, no.

[Host (possibly Bert)]

Okay, Sounds like there was an echo of a bathroom.

[Co-host 2]

He's just listening to himself.

[Host (possibly Bert)]

Oh, I gotcha. How you doing, man? Because the last time we talked to you, you were on with Anna Milfi and you guys said you were gonna go hang out over the weekend. And Jen Hobby thought that Anna Milfi was just being nice just to be nice on the air. I'm sorry, I didn't feel that.

[Co-host 2]

I mean, I really, I. I hope that it went well and I hope that she was just maybe embarrassed about being on the radio, but I Kind of got the vibe that she was placating you.

[Co-host 3]

I think she may have gone out with you and done all sorts of stuff to you.

[Host (possibly Bert)]

You think they went Kama Sutra page one to 120 this weekend?

[Co-host 3]

Yeah, I think she, I. I think she did stretches before she took him out. I think she limbered up, went into like a steam room. Loosen up the muscles. And I, I'm surprised you're even okay right now.

[Host (possibly Bert)]

Did you guys even meet this weekend?

[Justin]

Yeah, actually, we met up at a compound again.

[Host (possibly Bert)]

Okay, okay.

[Justin]

Saturday night. And 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.

[Co-host 2]

Why?

[Justin]

You know, seeing the age difference and everything, you know, what happened?

[Co-host 1]

Well, that didn't bother you at Jackie Lantern, so what was the difference?

[Justin]

Well, you know, I think, I think it's more on her part. You know, it really doesn't matter. You know, I can see her. I think she wants to date, you know, a guy her own age, you know, has his own house and all that stuff and making the big bucks, you know, But I guess I was too young for her. You know, we got. We get along just fine and, you know, we hung out pretty much for like two hours at compound and, you know, we danced and everything. I bought her a couple of drinks and laughed and had a great time.

[Anna Milfi]

Russian.

[Host (possibly Bert)]

So are you. Are you convinced that if she was younger or you were older that there would be a follow up date?

[Justin]

I'd like to think so. You know, I'd like Anna even if she was 65 years old. You know, I just, I think she's a really pretty woman. I like her personality. So, you know, what a good guy.

[Co-host 1]

What. So when did it. How did the date end? Like, I mean, how did, when did you know on Saturday that things were not gonna progress?

[Justin]

I guess. Well, I went to the restroom and came back and I was like, wait here. And I came out and then she was gone.

[Host (possibly Bert)]

She really was gone.

[Justin]

And then, you know, I was like. She called me and said she was waiting inside because it was cold, but, you know, compound so big, you know, heck, I couldn't find her after that. I was kind of. Kind of tipsy walking around, so.

[Host (possibly Bert)]

So there you were kind of like aimlessly searching for Anna Milfi.

[Justin]

Well, after that, I pretty much. I couldn't find her. She kept text messaging me like, hey, I'm waiting on you. I'm here. Where you Left me. So after that, I just snuck into VIP and started dancing with some random girls.

[Co-host 3]

So you just left her?

[Justin]

Oh, I mean, I couldn't find her when I came out, you know, I walked out of the bathroom, and I'm like, whoa, where'd she go? You know?

[Co-host 3]

So she's still wandering around compound like those Alzheimer patients that get out of the home that we hear.

[Justin]

Trying to.

[Co-host 3]

Find her way back.

[Host (possibly Bert)]

Justin, walking around compound, even right now.

[Co-host 2]

So you never saw her at the end of the night?

[Justin]

No, I never saw her at the end of the night. She sent me a text message, and she said, you know, did you get your ride home? And she was like, you know, we'll take you. And I said, yeah, I got my ride home. She was like, well, have a good night.

[Co-host 3]

So you blew her off?

[Co-host 1]

Dude, she still could have given you a ride home, even after all that.

[Host (possibly Bert)]

Well, I'm assuming you hooked up and you got a ride home from somebody else.

[Justin]

No, just one of my buddies drove me home.

[Co-host 3]

But you could have driven home in her Cutlass.

[Justin]

No, that's wrong. Come on.

[Host (possibly Bert)]

So here's the thing, though.

[Co-host 3]

I'm thinking, like, the whole way, 15 miles an hour.

[Host (possibly Bert)]

She's got those. She's only 45, man. I know she's only 45.

[Justin]

She looked really hot Saturday night, too. You know, she was banging.

[Host (possibly Bert)]

See, I'm thinking that the two of you guys really didn't want to find each other because you text her, you tell her exactly what bathroom you're in front of. She texts you back and says, I'll be right there. She walks back there, and then you guys see each other. Yeah, it's really pretty simple.

[Justin]

She says she was waiting inside to the left. You know how they block it off with a tent and compound, but, you know, there's, like, so many places right next to the bathroom. I didn't. I didn't really know there was a couple of people there, so, you know, it's hard to find people, you know, you got confused. I was confused.

[Host (possibly Bert)]

She won't come on with us this morning for whatever reason. I don't want to talk about it.

[Justin]

Okay. I don't want to embarrass her. You know, she's a mom. She has kids, you know, in the life.

[Host (possibly Bert)]

Yeah.

[Justin]

So I really don't care about my image, you know, I do at some point, you know, but it doesn't really matter to me.

[Co-host 2]

I think she felt ditched.

[Co-host 3]

Yeah, you blew her off, dude.

[Justin]

I was playing hard to get.

[Host (possibly Bert)]

No, you weren't.

[Justin]

Were you I'm just kidding.

[Co-host 3]

You're playing.

[Justin]

It's. We're just, we're just friends I guess, you know, but it's cool though, you know, not many 22 year old guys have, you know, a hot ass 45 year old mom as a friend, you know, so I mean, I hope we're friends, you know, for sure.

[Co-host 3]

I couldn't. I know I couldn't say that when I was 20 something.

[Justin]

Yeah, I know. So, you know, if I ever see her out again, at least, you know, we can talk and dance, you know, and just, you know, chit chat and all that. So.

[Host (possibly Bert)]

There was never any specific conversation by her though saying, you know what, this is just not going to work, let's just hang out.

[Justin]

Yeah, I think she's dating, you know, I think she's been in a relationship with, you know, a guy her age for the, for maybe the last couple of months. So, you know, just kind of left it at that, you know, I didn't really go on any further. And then, you know, she asked me about my dad and you know, I told him where he goes to party a lot. You know, I told her, you know, maybe that they should hook up or something.

[Co-host 2]

Do you think that you were like insulting her the whole night and maybe you just didn't realize you were.

[Justin]

No, you know, she told me she was like, you know, you're a very sweet young man, you're very polite, very mature, you know, I mean, obviously if she thought I was annoying and you know, a nuisance, she wouldn't have even called me to begin with to meet her at compound.

[Co-host 3]

You know, maybe you shouldn't have taken her to compound the first night.

[Justin]

Maybe I didn't actually. The thing is we didn't, I didn't take her there. She just showed up there and I was actually going somewhere else and she called me and said, where are you going? I said, I'm going to Fever. And she said, no, go to compound. So I went to compound, said, so it's kind of like it really wasn't even a set date.

[Co-host 3]

Maybe you should have like an official date and take her to one of them talk.

[Justin]

You guys could tell on the radio she really didn't want, you know, a set date, you know, she said it's my friend's, you know, birthday and we're going out to celebrate, you know, so.

[Host (possibly Bert)]

She'S doing the group date. That's what those 45 year olds do.

[Justin]

Yeah, the group thing.

[Host (possibly Bert)]

The group thing. All right, man, sorry it didn't work out for you. But you had a cool night with her? A couple of cool nights, yeah.

[Justin]

It was cool.

[Co-host 2]

Did you write any poetry?

[Justin]

No, I didn't write any more poetry.

[Co-host 2]

No poetry?

[Justin]

Actually, she told me Saturday that she had a poem for me.

[Co-host 1]

Really?

[Justin]

Yeah, but apparently I guess she doesn't want to read it. She must have forgot it.

[Co-host 3]

You went to the loo and then said F. U.

[Co-host 2]

That's a good starting point.

[Host (possibly Bert)]

Here she is.

[Co-host 1]

Oh, she's here.

[Host (possibly Bert)]

Yep, I think she's here.

[Co-host 2]

Okay.

[Host (possibly Bert)]

Hey, Anna.

[Co-host 3]

I can't wait to hear this.

[Host (possibly Bert)]

How are you?

[Anna Milfi]

Fine. How are you?

[Host (possibly Bert)]

Good. We were just talking to Justin about a very disappointing Saturday night.

[Anna Milfi]

Well, okay. Was he disappointed?

[Host (possibly Bert)]

Only that he couldn't like, you know, like finish off the night with you. That you guys lost each other. He said you had a great time, but you guys kind of like lost each other.

[Co-host 3]

You're one of those wanderers.

[Anna Milfi]

Yeah, well, it's the big place. It's. I lost him. He went to the restroom and I never saw him again. I thought maybe he ditched me, but that's. That's all right. That's okay. We had a good time.

[Host (possibly Bert)]

Justin, you weren't ditching her, right?

[Justin]

No, I wasn't ditching her. I came out of the restroom and I didn't see her. And so I tried to walk back, you know, just to wherever I thought we were at last. And I didn't see her. She said she's inside at a bar, but heck, you know, there's 20 bars in downtown.

[Zyn Nicotine Pouches Announcer]

That's okay.

[Anna Milfi]

We had a good time. It was fun. We were there with a bunch of girls and.

[Host (possibly Bert)]

Yeah, it's just a one time thing for you though. Anna, there's not going to be a follow up date or anything like that?

[Anna Milfi]

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.

[Host (possibly Bert)]

Okay.

[Co-host 1]

Yeah. Now I'm still just confused about how you can lose each other outside a bathroom. I mean, you know, I mean, I know that can be a place.

[Co-host 3]

Well, the losing I can understand. It's the.

[Co-host 1]

Because like never finding each other again.

[Co-host 3]

Right. Well, I can give you a perfect example at Compound. Saturday night when we walked in as we ran into Jen Hobby and we were with one of the owners of the club and we lost him. Like he kept walking and we stopped at the. Talk to someone, so. But we found each other again. Like you can always find each other, right? You know what I mean?

[Host (possibly Bert)]

Like text you say exactly where you are, right?

[Co-host 3]

Then it's like, okay, don't. Which is what happened. You said, boom, don't move. I'm coming right up there. And then we all walk up and there he is, and it's, you know, done and whatever.

[Host (possibly Bert)]

Either way, it doesn't matter. She's got a guy, she's seen that she's digging.

[Co-host 2]

So I think she ditched him.

[Host (possibly Bert)]

You think, Anna?

[Co-host 2]

I do.

[Co-host 3]

Did you?

[Anna Milfi]

I didn't hear that.

[Co-host 3]

Did you ditch him?

[Anna Milfi]

No, absolutely not.

[Co-host 1]

Did you make it a little bit.

[Co-host 2]

Too hard for him to find you?

[Anna Milfi]

No, I didn't. I really didn't. I really didn't. I enjoyed his company. It was. It was fun. And all the girls that were there just thought he was great, and he was very polite and we had a good time.

[Host (possibly Bert)]

It's got to be very flattering to you.

[Anna Milfi]

Yeah, it is. It was a little. It was a little embarrassing at first because I thought, you know, I'm too old for. For as old as my son. But. But it is a compliment. And. And like I said, he was. He was very nice. So he wasn't rude or anything or sarcastic about anything or, you know, he was very nice.

[Co-host 1]

So this was basically it. You just met up and that was all was intended to be. Like, this really wasn't a date.

[Co-host 2]

Like a real date date.

[Anna Milfi]

Well, if he wasn't 22, I would be interested in him. He's got a great personality.

[Host (possibly Bert)]

If he was 25, would that change things?

[Anna Milfi]

I don't think so.

[Host (possibly Bert)]

30? Would 30 change things?

[Anna Milfi]

Maybe 30.

[Host (possibly Bert)]

30.

[Anna Milfi]

Maybe 30. All right, Justin, I'm a young 40.

[Justin]

I have to call you back in eight years, I guess.

[Host (possibly Bert)]

Yeah, call us back in eight years. I'm sure we'll be doing the same thing. All right, you guys.

[Anna Milfi]

All right.

[Host (possibly Bert)]

You guys want to wrap this up? Am I forgetting anything?

[Co-host 1]

No, no.

[Justin]

I mean, just hopefully you guys will sell me a day, right?

[Host (possibly Bert)]

It sounds to me like you're doing okay for yourself, for sure.

[Anna Milfi]

Yeah, I think he is. And whoever gets to get on date with him or have a relationship with him is very lucky. So that's sweet.

[Co-host 2]

That's a nice endorsement.

[Justin]

Thanks a lot, guys.

[Host (possibly Bert)]

All right, you guys, we'll talk to you later.

[Anna Milfi]

Bye, guys.

[Justin]

The Birch Show.

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