Vault: This Voicemail Is Every Friend Group's Worst Nightmare

Summary

Podcast Summary: "Vault: She left a criticizing message about her friend's boyfriend"

The Bert Show
Date: July 6, 2026

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Episode Overview

This Bert Show "Vault" episode zeroes in on a relatable friendship dilemma: What happens when you vent a little too candidly about a friend's potential new boyfriend, only to realize you're way off-base—and you might have accidentally left those criticisms in a voicemail she hasn't heard yet? Hosted by Jeff with Jessica, her friend, and the usual crew, the discussion is equal parts cringe, humor, and real talk about communication in friendships, oversharing, and judging others.

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Key Discussion Points and Insights

1. Jessica’s Voicemail Mishap (01:17–04:10)

• Background: Jessica admits she’s a serial long-voicemail-leaver, particularly with out-of-state friends. Her friend teases her about her four-minute updates covering everything from travel plans to pet tricks.
  Jessica: "First of all, I think I'm in danger of losing my best friend. Oh no. [...] It’s because I talk too much and I leave too much information on voicemail." (01:17)
• The Mess Up: Jessica witnesses a high school acquaintance on her friend’s Facebook, judges his lifestyle based on photos (“cheesy and lame”), and proceeds to rant about him, leaving a critical voicemail.
  Jessica (about the message): "I decided that based on the photos, he was a little cheesy and lame and, you know, all these other things." (02:32)
• Realization: Mid-message, her friend calls. Excited, Jessica flips to the call, only to discover during the conversation that her friend is actually dating (!) the guy she was just ripping apart.
  Jessica: "Turns out that they are, like, kind of starting to date. Oh, no. Oh, no." (04:00)

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2. The Fear of Being Found Out (04:11–05:46)

• Anxious Wait: Now in limbo, Jessica fears her friend will eventually hear the mean voicemail, and she dreads the fallout since she was polite during their real-time conversation. Jessica: "I know at some point she's going to hear that voicemail and then I'm going to have to... She’s going to feel terrible because I said all those bad things and she actually likes this guy." (04:41)
• “Hypocrite” Moment: Jessica feels guilty for being two-faced—nice on the phone, judgey on voicemail. Jessica: "When I was on the phone with her, I didn't say bad things to her face, so. Such a hypocrite." (04:54)

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3. Could She Get Away With It? (05:07–05:44)

• Jeff’s Hopeful Theory: Jeff suggests her friend may just delete the voicemail after their conversation, rendering the issue moot.
  Jeff: "When I get off the phone with you, my assumption is you were just leaving the details of the voicemail that you and I talked about live. So I just immediately delete and move on." (05:18)
• Gender Divide: They debate if this is more of a “guy” reaction, while Jessica insists women would do the same. Jessica: "No, we do that same thing." (05:36)

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4. The Dread of the Unknown (06:24–07:33)

• Jessica’s Friend’s Point: “You’ll never, ever know”—the worst part is the lingering uncertainty; her friend might listen and never say anything but keep her distance. Jessica's Friend: "It is possible she could listen to it and never tell you and never bring it up...You’ll know if they get married and you don’t get invited to the wedding." (06:25)
• Jessica’s Dilemma: Wonders if she should ask her friend outright. The others joke she can concoct a story about "what was on the message" to test if it was heard—but Jessica fears this would just draw attention. Jessica’s Friend: "All you have to do is call her back today and ask her if she listened to the message because you left...make something random up." (06:58)

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5. Reflection and Growth (07:41–09:13)

• Judgement & Maturity: Jessica recounts how, during their chat, her friend reflected on being less judgmental as she ages, prompting Jessica to feel extra guilty. Jessica: "She started to go off into this tangent about how now that she’s a little bit older, she doesn’t judge people as harshly and gives everyone a chance...I really started to feel bad because I was like, oh my gosh, who am I to judge this person?" (07:41)
• Next Steps: Jessica isn’t sure when they’ll speak again, but she’s now hyper-aware and hopes to gauge her friend’s mood in the next contact. Jeff and others suggest that if her friend replies with a breezy “Hey, call me,” she probably didn’t listen—or didn’t mind.
• Silver Lining: They joke her friend may simply have a different taste ("she may find his Trans Am with the T-tops totally sexy") and everything will work out.

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Notable Quotes & Moments

• On Friendship Communication:
  "It's almost annoying the way Jessica leaves this girl voicemail messages because...we'll leave like a 4, 4 minute message with an update of everything of the past two weeks." – Jessica’s Friend (01:51)

• On Gossip & Hypocrisy:
  "I was so in the zone of being mean...I just click over. So she and I start talking...Turns out that they are like, kind of starting to date." – Jessica (03:44–04:01)

• On The Dangers of Voicemail:
  "I just can’t believe—this is the danger of voicemail." – Jessica (06:49)

• On Not Knowing:
  "You will never, ever know. Because it is possible she could listen to it and never tell you and never bring it up...You’ll know if they get married and you don’t get invited to the wedding." – Jessica’s Friend (06:24)

• On Second Chances:
  "Now that she's a little bit older, she doesn't judge people as harshly and gives everyone a chance." – Jessica (07:41)

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Recap Flow and Tone

The conversation is lively and teasing, true to The Bert Show’s friendly, bantering style. While Jessica’s situation is classic cringe, the crew keeps it lighthearted: they tease her but ultimately show empathy, offer theories for damage control, and pivot the discussion toward self-reflection and giving others (and ourselves) grace.

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Timestamps for Key Segments

• 01:17 — Jessica admits fear of losing her friend and explains her long voicemail habit.
• 02:32–03:27 — She details her critical voicemail about her friend’s new boyfriend.
• 04:00–04:41 — Realizes during the call her friend is dating the criticized guy.
• 05:07–05:44 — Jeff proposes that her friend might have deleted the voicemail.
• 06:24–06:37 — The others suggest she may never find out if the voicemail was heard.
• 07:41–08:24 — Jessica reflects on feeling guilty and her friend’s comments on not judging.

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Final Thoughts

This episode delivers a cautionary—and very funny—tale about the perils of gossip, the permanence of digital communication, and the art of being kinder, both to others and ourselves. Jessica’s anxiety is familiar for anyone who’s ever overshared, while the group’s solutions (and semi-evil jokes) keep it engaging and relatable. Will Jessica ever find out if her friend listened? Will it torpedo the friendship (or just embarrass her forever)? The Bert Show leaves it open, for maximum suspense—and maybe a follow-up story.

Transcript

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[Jeff]

The Bird Show Jeff and Jessica are in the middle of sort of a situation that has to end sometime over the next 24 hours.

[Jessica's Friend]

It's not me. I didn't do anything.

[Jeff]

It's just you sitting back enjoying the ride for once.

[Jessica's Friend]

There is a big screw up in the Dollar Castle in Sandy Springs and I didn't do it. Okay, 100%. Jessica.

[Jessica]

Jessica, what'd you do? Well, first of all, I think I'm in danger of losing my best friend. Oh no.

[Jeff]

Seriously?

[Jessica]

Yes. And you know what? It's because I talk too much and I leave too much information on voicemail and I'm not even going to do that anymore. Uh oh. What happened? Well, I have a like one of my best friends, she doesn't live here. We don't talk on the phone that much. I mean, we exchange voicemails a lot because we play phone tag. So we leave a lot of information on voicemail. Facebook, whatever.

[Jessica's Friend]

It's almost annoying the way Jessica leaves this girl voicemail messages because it's like, hey, just call, say hey, blah blah blah. Jeff and I are on our way to the airport because we're going to Panama. I don't even know if I told you we were going to Panama. We're going to Panama. And it's so weird because Jeff's co worker Jen is going to be in Central America and his coworker Bert is going to be in Central America. And you know, Bert's a surfer and Jen's going to surf camp. So that's really cool. But they're not going to be together. Obviously, they're going separately. Anyways, we've got that going on. And Sasha learned a new trick. And we'll leave like a 4, 4 minute message with an update of everything of the past two weeks. All sorts of random information. I make fun of her for it, but that's how she communicates with, like, two or three of her friends from other states. Okay.

[Jessica]

Yeah, so that's exactly what I do. And I got on Facebook the other day and I noticed that she's friends with this guy from our past. And you know how when you're friends with someone on Facebook, you can see even if you're not friends with them, you can see their friends pictures. Right. So I noticed that she's now friends with this guy that we both used to know. So of course I went and looked at all of his pictures and I saw all these photos. And so I, you know, I decided that based on the photos, he was a little cheesy and lame and, you know, all these other things. So I called her to leave a message. And we'd been playing phone tag for like a week. So I'm on her voicemail leaving this really long message. Oh, my God. Can you believe. I can't believe you're friends with this guy. What a cheese ball he turned out to be. I mean, and then I'm like rattling off this list of things like, can you believe this? Can you believe that? Blah, blah, blah, blah.

[Jessica's Friend]

Making fun of his car. The way he dresses now. Oh, no. Like, the way he's decorated the inside of his house, how he was cool in high school, but has grown up to be the biggest redneck dork ever.

[Jeff]

Just every area ripping on this guy, Ripping.

[Jessica]

And I'm like, blah, blah, blah. And I'm so in the zone of being mean that I see my phone beeps. I'm getting a call, and it's her. I'm like, oh, my God. So excited to actually talk to her in person that I just click over without ending that first call. I just click over. So she and I start talking, blah, blah, blah. We get into the conversation of this guy. Turns out that they are, like, kind of starting to date. Oh, no. Oh, no. Insert face. And I'm like, oh, my gosh. So tell me about this guy. You know, I can't found you on Facebook. She's like, yeah. Oh, my gosh. I have so much to tell you. We actually went out to lunch. We this and we that. And, you know, she starts going into all these things About. I'm like, well, so. I mean, are you dating? And she's like, I don't know. I think so. I hope so. And so, you know, I started talking about that in the back of my mind. I'm thinking, oh, my God, I hope that that voicemail I left somehow erases, which I know it won't. She doesn't check her voicemail very much. But I haven't heard back from her after our. After we actually talked. So I know at some point she's going to hear that voicemail and then I'm going to have to. She's going to feel terrible about it because I said all those bad things and she actually likes this guy. And when I was on the phone with her, I was, you know, I didn't say bad things to her face, so. Such a hypocrite.

[Jeff]

Now, you might have saved yourself. You might have saved yourself, and here's why, okay? If the same chain of events happened to me and I left a voicemail, but then I talked to the person as I was leaving the voicemail, when I get off the phone with you, my assumption is you were just leaving the details of the voicemail that you and I talked about live.

[Jessica's Friend]

Great point.

[Jeff]

So I just immediately delete and I move on to the next voicemail.

[Jessica's Friend]

Is that a guy thing, though, or do girls do that?

[Jessica]

No, we do that same thing.

[Jeff]

Cause why listen to a message when you just talk to the person? So she might have just deleted it and moved on.

[Jessica]

Now, that's a great point.

[Jessica's Friend]

How far into the message was it before you started ripping on this guy? Like, was it immediately like, hey, oh, my God, this dude on Facebook, blah, blah, blah, blah, blah? Or was it like, hey, I got so much to tell you about, and then like, it was the second or third thing down the list?

[Jessica]

Yeah, it was the second or third thing, you know, because you know, when I talk crap about someone, I don't just jump right into it.

[Jessica's Friend]

You gotta warm her up.

[Jeff]

You gotta take a pace lap. You gotta throw bp. Yeah, you gotta stretch a little bit.

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[Jeff]

I bet that if you're leaving, if you're one of those people that leaves long messages, and the third thing you leave in that message is ripping on the guy she three. Seven'd you.

[Jessica's Friend]

Now, you know what the bad thing about that is? You will never, ever know. Because it is possible she could listen to it and never tell you and never bring it up and just never bring up this guy. And you'll know if they get married and you don't get invited to the wedding.

[Jeff]

And I don't think that you have the kind of personality that can allow it just to sit. Like, at some point, I think you're gonna break down and say, did you ever listen to that voicemail message I left you?

[Jessica]

You're probably right. I just can't believe this is the danger of voicemail.

[Jessica's Friend]

I.

[Jeff]

No, it's the danger of talking too much.

[Jessica's Friend]

Exactly. Thank you.

[Jeff]

And judging.

[Jessica's Friend]

I solved it. By the way, Bert, while using your tip, all you have to do is call her back today and ask her if she listened to the message because you left him. You included something in that message that you haven't talked to her about. So, hey, did you listen to the message and hear that and just make something random up? Like, Jeff and I test drove the car that you own. We might get one or something totally random, but would be relevant? No, Bad Wendy.

[Jessica]

Because then what if the message is still saved in her voicemail, Then she's gonna go back and listen to it.

[Jeff]

She'll be intrigued to listen to it.

[Jessica]

You can't do that.

[Jeff]

This is a ticking time bomb right here. Wow.

[Jessica's Friend]

And I love the fact you just

[Jessica]

gotta hold out and see.

[Jessica's Friend]

And I love the fact that you'll never find out.

[Jessica]

Well, she may say something. She would say something. If she hears it and she's offended, is she the kind of friend that would say something? Yes. Because, you know, another thing is when we were talking about. When we were talking about that guy, you know, and we were kind of talking about them dating, she started to go off into this tangent about how now that she's a little bit older, she doesn't judge people as harshly and gives everyone a chance. Seriously. And I really started to feel bad because I was like, oh, my gosh, who am I to judge this person? I mean, really. And then she's like, you know, I just. I don't like to judge people anymore. And she kind of went a little bit under that. So, yeah, she might say something about that.

[Jeff]

So when is the next time that you are supposed to have communication with her?

[Jessica]

I don't know. I mean, it's just whenever. I mean, there's no time. It's just I'll probably start calling her more often now so I can see if she's gonna call me back.

[Jessica's Friend]

Well, the way that you guys trade voicemail messages, if you get one from her, that's just, hey, call me then. You know.

[Jeff]

You know what it might be also? It might be when she goes out with this guy for a second time or something, she may call you back and just say, you know what? You totally miss pegged this guy. He's so not what you think.

[Jessica's Friend]

Or she may, while you find it a little rednecky, she may find his Trans Am in the T tops totally sexy.

[Jessica]

Hey, those are hot.

[Jeff]

All right, Jess, keep us posted.

[Jessica's Friend]

All right?

[Jessica]

Okay.

[Jeff]

You're on the Birch show.