Vault: You'll Never Believe What Happed To Jamie At A Coffee Shop

Summary

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The Bert Show – "Vault: You'll Never Believe What Happened To Jamie At A Coffee Shop"

Podcast Host: Pionaire Podcasting / Bert Show Cast (Bert, Kristin, Abby, Cassie, Tommy, et al.)
Release Date: November 7, 2025

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Episode Theme & Overview

In this episode, the Bert Show crew revisits the dramatic, humorous, and disappointing story of Jamie Massey's coffee shop encounter, which started off like a rom-com and ended with a jaw-dropping twist. Jamie recounts her experience—what seemed like a promising romantic serendipity turns into a cautionary tale about hidden marital status. As Jamie grounds the listeners in her personal disappointment, other callers chime in with their own stories of unknowingly dating married men, creating a larger conversation about dating, trust, and red flags.

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Key Discussion Points & Insights

1. Jamie's Coffee Shop Meet-Cute

• The Setup (01:12–02:27)

  • Jamie recalls going to her local coffee shop, waiting in a long line, and chatting with an unusually attractive man behind her. Their interaction is playful and natural.

  • When the credit card machine fails, the man chivalrously buys her coffee, and they swap contact info (his card with number and email).

    "He was very chivalrous and was like, let me take care of your coffee, I'll pay for it." —Jamie, [01:33]

• The Playful Reconnection (02:27–03:19)

  • Over the week, Jamie and the man exchange lighthearted emails. They set a plan: if he’s in line at 10 AM next Sunday, she’ll buy his coffee.

  • Jamie is nervous, arrives early, and eagerly awaits his appearance.

    "I've got the newspaper, I order a cup of coffee and I sit down. And of course, every person that walks by, I'm like looking up..." —Jamie, [02:47]

• A Near Miss and a (Slightly) Happy Twist (03:19–04:22)

  • The guy doesn't show by 10, Jamie leaves, feeling stood up—but then, as she's pulling out at a red light, he arrives!

  • She turns around, treats him to coffee, and they chat briefly before agreeing to reconnect later.

    "He comes flying into the parking lot... I like, you know, turn my car around real quick and we go in the coffee shop." —Jamie, [03:54]

2. The First Date… and The Bombshell

• Tour and Chemistry (04:22–05:48)

  • That evening, he invites Jamie to his business, gives her a tour, and then takes her out for what feels like an amazing first date, marked by great chemistry.

    "It's like total chemistry. You just hit it off and you just get along... he's cute, this is perfect." —Jamie, [05:16]

• The Shocking Revelation (05:48–07:24)

  • Midway through dinner, Jamie jokingly asks, "You're not married, are you?" The mood shifts instantly; the man admits he is, in fact, married.

    "He goes, 'how'd you know to ask that?'" —Jamie, [06:10]

    "I was totally kidding. And he goes, how'd you not ask that? ...He says, 'well, I didn't know how... I just like to meet people, and you're a beautiful girl.'" —Jamie, [06:24, 06:47]

  • Jamie is flabbergasted and humiliated, learns he had no intention of telling her, and leaves in shock.

    "I mean, I was absolutely humiliated. Humiliated." —Jamie, [07:24]

3. Aftermath & Emotional Fallout

• Jamie Processes (07:24–09:24)

  • Jamie details feeling devastated but also with some dark humor about her luck in love.

  • She emphasizes she’s held onto this story for days, feeling the need to share.

    "You know, it's just... I, like, cried all the way home... And then by the time I got home, I'm like, this is freaking perfect. It's just perfect." —Jamie, [09:03–09:10]

    "Now it's like, okay, I don't think there's anything else that can happen on a date to me that has not happened already at this point." —Jamie, [09:26]

4. Callers Share Their Own Shocking Experiences

• Call-In Segment: Others' Stories of Hidden Marriages

  • Multiple callers (Colleen, Maggie, Jessica, Michelle) recount their own bewildering discoveries that men they were dating were already married.

    • Colleen (11:04): Dated a man for a month. Found out he was married when he referred to 'my first wife.'

    • Maggie (11:52): Guy admits to being married after weeks of daily calls and dates.

    • Jessica (13:32): Lived with her boyfriend for over eight months before his wife showed up at their shared apartment.

    • Michelle (14:44): Dated a man for five years, even got engaged, before uncovering his marriage through personal investigation.

      "Five years. I never suspected a thing." —Michelle, [14:49]

      "And I said, well, what's that brown covered thing in the backyard? He goes, what are you doing out here? He goes, oh, my God. He goes, my wife's coming home." —Michelle, [15:40]

• Common Patterns & Reflection

  • Many of the men weren’t wearing rings and justified it for various reasons.

  • The segment underscores how common and devastating this scenario is for many women.

    "This guy wasn't wearing a ring either. And I asked him, I said, why don't you—Where's your ring? ...He said, I don't believe in wearing rings." —Jamie, [13:05–13:15]

5. Group Support and Closing Thoughts

• The cast offer support and laughter to Jamie and the callers, reinforcing the message that it’s not their fault, and anyone can be fooled.

• Jamie sums up with some dark humor and relief she found out early before investing more.

  "At least I found out in the first, you know, week you didn't waste too much time." —Jamie, [17:10]

  "I'm never getting married." —Jamie, [16:40]

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Notable Quotes & Memorable Moments

• Jamie’s At-the-Light Surprise:

  "He comes flying into the parking lot... I like, you know, turn my car around real quick and we go in the coffee shop." —Jamie, [03:54]

• The Gut-Punch Admission:

  "'You're not married, are you?' He goes, 'how'd you know to ask that?' ...'Yeah, I am actually. I've been married about two years.'" —Jamie, [06:10–06:18]

• Jamie's Reaction:

  "I mean, I was absolutely humiliated. Humiliated." —Jamie, [07:24]

• Listener Solidarity:

  "Five years. I never suspected a thing." —Michelle, [14:49]

• Group Humor Amid Disappointment:

  "You know, the next one's gonna be gay." —Cast, [09:44]

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Timestamps for Important Segments

• Jamie's Coffee Shop Story Begins: [01:03]
• Playful Emails & Nervous Wait: [02:27]
• Red Light Encounter: [03:54]
• First Date/Tour: [04:22–05:48]
• Revelation of Marriage: [05:57–07:24]
• Listener Call-in Stories: [11:04–16:25]

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Tone & Style

The conversation is candid, irreverent, full of humor even in disappointment, and deeply empathetic. The Bert Show cast and listeners create a space where heartbreak is shared, commiserated, and even laughed at, maintaining an authentic and uplifting energy throughout.

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Takeaway

This episode combines real-life dating debacles with comic relief and heartfelt solidarity. Jamie’s coffee shop story is both entertaining and relatable, sparking a larger dialogue about the complexities—and occasional absurdity—of modern romance. If you’ve ever had a romantic situation go awry, you’ll find yourself nodding (and maybe even laughing) along.

Transcript

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[Host/Moderator]

The Birch show so on Friday we talked to Jamie Massey about the coffee shop incident that happened I guess the week before or two weeks before.

[Jamie Massey]

Was it a week before? Yeah, it was two Sundays ago. I'm in line Sunday morning around 10 at the coffee shop by my house and the line was really, really long and I'm standing in line and this really attractive man comes and gets in line behind me and it's kind of an older place, like there's a lot of older people. So I was surprised to see a young good looking guy in the coffee shop. Well, we get the line was so long, it was about 10 minutes of just talking. We struck up a conversation and when I get up I place my order. Their credit card machine was down so he was very chivalrous and was like, let me take care of your coffee, I'll pay for it. I was like oh no, no, I'll run to the atm. Well, he insisted. He paid for my coffee and so we talked a little bit after that and I said I want to repay you. So he gave me his card with his number on it and his email address. So we corresponded a couple times during the week via email. I wasn't going to call him, but via email. We corresponded a couple times during the week and I was like I want to repay you because he was cute. And so the correspondent ended up with okay, I'm going to be in line at the coffee shop 10 o' clock Sunday morning. And if you're the next person in line, I will buy you that cup of coffee, which is so cute.

[Jen]

And this is like exchange, going back and forth, kind of playful, kind of.

[Jamie Massey]

Playful, not committal, but not, you know, playful in a undertone kind of way. Like, it was not blunt flirting or blunt, you know, it was just kind of like, hey, I'd love to repay. Like, hey, well, I'd love to see you again kind of thing. And it was just kind of chemistry, you know.

[Jen]

Okay.

[Jamie Massey]

So of course I like couldn't sleep Saturday night. I was so nervous. But I also found out I had to work at the Braves game and I was supposed to be at Turner Field at 10:30. So this was gonna be kind of cut short, unfortunately. But so I get to the coffee shop around 9. I get there early, kind of get a good seat on the couch, I've got the newspaper, I order a cup of coffee and I sit down. And of course, every person that walks.

[Jen]

By, I'm like looking up every time the bell on the door jingles and somebody walks in, you're like, who's that?

[Jamie Massey]

So 9 o' clock comes, 9:15, 9:30, 9:45, 10 o' clock comes, no guy. And I have, oh, you're feeling like stood up. I have to leave, you know, and I've got like. I stuck it out as long as I could. I even called my boss down at Turner Field and I was like, yeah, I'm gonna be a little bit late. I've got some stuff going on. So I stayed till about 10:05 and I was like, I just, I have to go. So I get in my car and I start to drive out and there's a red light coming out of the parking lot. And I'm at the red light and he comes flying into the parking lot.

[Jen]

Like out of control driving?

[Jamie Massey]

Yeah, like, kind of like he feels like he's late. So he sees me and I see him and he waves and so I like, you know, turn my car around real quick and we go in the coffee shop and I buy him a cup of coffee and we talked for like another 10 minutes or so. And I said, I'm so sorry, I have to leave. And he's like, oh, well, you know what, Give me your phone number and let me call you a little bit later and we can talk. So he asked for my digits, so I said, okay, I will be home around 5 o'. Clock.

[Jen]

I think that's so funny that you were at the red light.

[Host/Moderator]

What If I were, my thing is that you stayed for like 5min later, you stayed late. If you had left right at 10, you wouldn't have seen him at the light.

[Jamie Massey]

All these things could have happened. So I go to the Braves game at work, I come home, I'm kind of chilling a little bit and at 5:30 my phone rings and he calls. So we talked on the phone for about half an hour, 35 minutes and he finally says, well, I'm at work, I'm wrapping things up. I'd love for you to come down and see where I work because he owns his own business, I'd love for you to come see it and maybe we can grab some dinner. So I'm thinking, awesome. So I said I'll be there at 7:30, get in my car, you know, shower, get ready, I'll do all the things, shave my legs, you know, do all the things you do. And I drive down to his place of business and he's there. He gives me a hug, he takes me on a tour of the place. It's all so exciting. And we're talking and we're laughing. It's like total chemistry. You just hit it off and you just get along. And so I take the tour and I'm thinking, okay, he's like successful, he's got his own business, he's cute, this is perfect.

[Jen]

You're like, what's wrong with him?

[Jamie Massey]

Yeah. So we walk down the street and there's like a ton of restaurants and stuff. So he picks out a restaurant and we go in and we sit down and we order dinner and dinner comes and we are just talking and laughing like we've known each other forever.

[Host/Moderator]

Awesome.

[Jamie Massey]

And at some point, oh no, oh no, oh no. Uh oh.

[Jen]

The pause is scaring me for some reason.

[Jamie Massey]

It's almost like I'm gonna get upset about this. I said to him, so tell me a little bit more about yourself. I said, haha, you're not married, are you? He goes, how'd you know to ask that?

[Jen]

Shut up.

[Host/Moderator]

You're kidding me.

[Jamie Massey]

He was married?

[Host/Moderator]

No.

[Jen]

You're kidding me.

[Host/Moderator]

How did you know to ask me that?

[Jamie Massey]

Didn't wear a ring. No.

[Host/Moderator]

See Jen, hobby.

[Jen]

What you just say Jamie, I'm sorry.

[Jamie Massey]

I know. So he's like, yeah, I am actually. I've been married about two years. And I said, were you? I mean the look, I still can't, I still can't believe that I even asked that. I was totally kidding. And he goes, how'd you not ask that? I was like I was joking. And he says. He says, well, I said, why didn't you tell me that? And he said, well, I didn't know how. And plus, you know, I just like to meet people, and you're a beautiful girl. And I said, does your wife know that you're out here meeting people? And he goes, oh, no, I'm not gonna tell her about this. And I said, when were you planning on telling me? And he said, well, I wasn't gonna do it today. Maybe, you know, like down the road.

[Host/Moderator]

Are you kidding? He said that.

[Jen]

You are kidding me.

[Jamie Massey]

And I said, I mean, I was absolutely humiliated. Humiliated.

[Jen]

So what happens then? Like, do you just, like, get up and walk out?

[Jamie Massey]

Like, I mean, I sat there for like 4 minutes and listen to him BS just babble, just on and on and on. And finally I just said, you know what I mean? You put yourself out there like that, you know, and you know that they know that you're putting yourself out there like that.

[Host/Moderator]

There's no reason for you to be humiliated. There's no reason for you to be humiliated.

[Jen]

He should be.

[Jamie Massey]

You cannot help. You just can't help it. So I just said, you know what? I've got to go. I'm. I just. I need to get out of here. And fortunately, my car was not too far outside the restaurant, and I went and got my car and just started bawling.

[Jen]

Oh, I am so sorry.

[Co-host or Friend]

I'm surprised he told you.

[Ryan Seacrest]

I am.

[Co-host or Friend]

If he would have gone that far, if he invited you out, if he took you to show you his show off his business, took you out for food, and then he told you that quickly, like, there's something about that that.

[Host/Moderator]

Well, she asked point blank, though he.

[Co-host or Friend]

Wasn'T going to bring it up himself. He had other int.

[Jamie Massey]

When I said to him, so, are you married? The look on his face. We were smiling, laughing, and it went, like, blank. And since then, I know somebody who knows somebody who knows him.

[Jen]

Okay, so.

[Jamie Massey]

And he is. After. After I called them and asked them about that, they went to that person. That person went to the other person and confirmed it.

[Jen]

That he's married?

[Jamie Massey]

Yeah.

[Jen]

Oh, that is so disappointing. That is so awful.

[Jamie Massey]

You know, it's just. I, like, cried all the way home, and then by the time I got home, I'm like, this is freaking perfect. It's just perfect. It just. It's just kind of the way that my little dating life has been going. And it just. It's entertaining to me at this point. It is entertaining to me because you've.

[Jen]

Told us you're, like, swearing off men.

[Jamie Massey]

I have had, like, in the past three or four months, everything but this happened. And now it's like, okay, I don't think that there's anything else that can happen on a date to me that has not happened already at this point. This one kind of came out. I'm not gonna lie. It surprised the hell out of me.

[Co-host or Friend]

You know, the next one's gonna be gay.

[Jamie Massey]

That's gonna happen too, I'm sure. I don't know. I just. Yeah. So that was my coffee shop update.

[Jen]

Your serendipity supposed to be romantic like that? What was the Tom Hanks, Meg Ryan.

[Jamie Massey]

Like, you've got mail. Yeah. Yeah. And the problem is that I sat here and listened to Jen just go on and on on Friday. This could be the one. It could be serendipity. It could.

[Jen]

Oh, yeah, I got him. Like, when you were telling that story, I'm like, I've already got you walking down the aisle.

[Jamie Massey]

Oh, I totally. She's planning my kids too.

[Host/Moderator]

You know, mostly he had already done it, so it sucks.

[Jen]

That sucks. I don't know what else to tell you, but that's awful.

[Jamie Massey]

And I have held this for days and days and Then starting at 5:30 this morning, all the way up until now, and I just wanted to tell you guys so bad, and you were like, da, da, da, da.

[Co-host or Friend]

She was tagging out traffic reports with, and I'm Jamie Massey and went out with the merry guy this weekend.

[Jamie Massey]

I just feel sorry for his wife. I mean, I certainly hope that maybe he learned a bit of a lesson there.

[Jen]

So he really.

[Jamie Massey]

I.

[Jen]

Man, he thought you were going to go along with it.

[Jamie Massey]

I don't. I don't. I mean, I don't know.

[Jen]

There's some moral support for you.

[Host/Moderator]

Jamie's not the only one this happened to. Colleen says don't feel bad because it took him longer to tell her. Hey, Colleen.

[Caller - Colleen]

Hey. I just want to say don't feel bad. I dated a guy for almost a month before I figured it out.

[Jamie Massey]

Oh, my gosh. How did you find out?

[Caller - Colleen]

We got on to dinner and before we had ordered, he said something about my first wife. And I kind of said, okay, how many wives have you had? Because, well, I've been married once and I'm married now. I said, okay, what did you do?

[Jamie Massey]

Did you just, like. Because, I mean, when he. When I found out that I sat there because I think I was in shock. And I sat there for like five minutes and listened to him BS me. And then I got up and just said I had to leave. What did you do?

[Caller - Colleen]

Well, I was in Boston at the time and had transportation, so ordered the most expensive thing on the menu, let him take me back to the hotel. And didn't hear from him ever again. Didn't call him, nothing.

[Jamie Massey]

Good for you.

[Ryan Seacrest]

Awesome.

[Leah Thomas]

Thanks.

[Host/Moderator]

Colleen. Maggie. Same thing happened to Maggie online, too.

[Caller - Colleen]

Yes. I was with friends at Eclipse Saloon one night and met this beautiful guy. We danced all night, had a great time. I gave him my phone number, not really thinking anything would come of it. And for a couple of weeks, he called me every day. We talked. And I was thinking, you know, this has to be too good to be true. And we decided to meet up again at Eclipse. Elena. And we were talking, and when I was listening to Jamie's story, I was like, that's exactly what happened to me because we were having a great time. And I was like, you're not married, are you? And he was like, yeah. And I was just shocked. And I was like, you know, how long have you been married? And he said, a couple of months.

[Jen]

Months?

[Jamie Massey]

Yes.

[Caller - Colleen]

And I was like, well, does your wife know about this? And he said, yeah, she's actually meeting me up here in a few minutes.

[Jamie Massey]

You're gonna get a little freaky.

[Caller - Colleen]

So at that point, I dipped. I was not staying around for that. And he continued to call for about another week, but I just ignored his calls.

[Jamie Massey]

And did he. Was he wearing a ring?

[Caller - Colleen]

No, he wasn't.

[Jamie Massey]

This guy wasn't wearing a ring either. And I asked him, I said, why don't you What? Where's your ring?

[Caller - Colleen]

Exactly?

[Jamie Massey]

And he said, I don't believe in wearing rings.

[Host/Moderator]

Of course not.

[Jamie Massey]

Well, now. Yeah. Because you couldn't pick up chicks.

[Host/Moderator]

Yeah, sorry. Thanks for the call. Now, number on line one is Jessica. Who needs the voice disguiser?

[Jamie Massey]

Phil, it's on.

[Host/Moderator]

All right. Hey, Jessica.

[Caller - Colleen]

Hi.

[Host/Moderator]

So the same.

[Jamie Massey]

We're calling.

[Host/Moderator]

Yeah. Who were calling? Jessica. Same thing happened to you?

[Caller - Colleen]

Yes. It was a little worse, though, for me. I was actually with this guy. He was really my first, like, boyfriend. We were together for a long, long time. And I was. I found out. I was surprised when his wife came to our apartment where we were living together. Yes. We were living together. And his wife actually showed up at our apartment. And she's like, well, who are you? They were supposed to be just separated, of course. And like, I never knew he was married at all. I knew he had a child. They had a three year old little boy. And I knew he had a child. I Did not know that they were actually married. And it was. Oh, my God. It was the hardest thing for me, like, cope with. Because we had been together for so long.

[Host/Moderator]

How long? How long had you been together?

[Caller - Colleen]

We were together for almost eight and a half months.

[Jen]

Okay, eight and a half months. And you did not know he was married?

[Host/Moderator]

That's nuts.

[Caller - Colleen]

And it was horrible, Jessica.

[Host/Moderator]

Sorry about that. But you know what? Michelle just called up and eight months is dropping the bucket to how long.

[Jen]

She was with the guy.

[Host/Moderator]

Hey, Michelle.

[Caller - Colleen]

Hi.

[Host/Moderator]

Do you need the voice disguiser?

[Caller - Jessica]

No.

[Jen]

Okay.

[Host/Moderator]

How long were you together?

[Caller - Jessica]

Five years.

[Jamie Massey]

Five years?

[Caller - Colleen]

Five years.

[Caller - Jessica]

I never suspected a thing.

[Jen]

You're kidding.

[Caller - Jessica]

No, no, no. He even. He went as far as to ask me to marry him. We went ring shopping. We were dead serious. My daughter, you know, she used to call him Daddy. I mean, everything was going smoothly. And I had taken an investigations class, and during that class, I received some software that I, you know, investigated people. And I found some stuff on him that really I had to question. And during the course of it, I had called him and I had confronted him, and he said, well, yeah, so what? I said, so what? You're married and it doesn't mean anything to you? And I was like, no. What are you going to do about it? So I googled his address, and my daughter and I went down in front of his house, and we're sitting in front of his house, and I called him on his phone and I said, you know, you really need to mow the grass.

[Jamie Massey]

What do you mean?

[Caller - Jessica]

And I said, well, what's that brown covered thing in the backyard? He goes, what are you doing out here? He goes, oh, my God. He goes, my wife's coming home. I said, yeah. And that's the point is I'm gonna sit here until she does.

[Host/Moderator]

Oh, my God.

[Jamie Massey]

So did you talk to her? You chickened out?

[Caller - Jessica]

I chickened out.

[Jen]

I couldn't do it. Did you ever talk to her?

[Caller - Colleen]

No.

[Caller - Jessica]

But I gave him one last booty call and said, that's it, you know, you will never ever see. And he called. I mean, one time he called 42 times in one day.

[Jen]

Whoa.

[Host/Moderator]

42 times he lived. Were y' all living together?

[Caller - Colleen]

No. No.

[Jen]

Okay.

[Caller - Jessica]

That's just it. He was convenient. He was always at my house. He would come to my house, you know, morning, noon and night. I never suspected it because he was always available. You know, I didn't have his cell. I didn't have his house number. But, you know, like everybody else, you have a cell phone and a house phone. So it doesn't really, you know, you don't question that.

[Host/Moderator]

And he never went over to his house or.

[Caller - Jessica]

I know, I know because he said he lived with his sister and that, you know, it was easy for him to come to me. And I was just so stupid and naive and so crushed when I found. I just couldn't believe that somebody would carry this on for five years.

[Jamie Massey]

I'm never getting married.

[Jen]

But you had to. You had to know something was up in order to investigate him.

[Caller - Jessica]

It was just, you know, there was something in the back of my mind that things just didn't seem right because he started lying and his lies started catching up with him one after another. And I'm thinking, okay, I'm gonna catch him in something. So, yeah, there was something in the back of my mind that just didn't seem right.

[Jamie Massey]

God, these poor women that are married to these guys that just.

[Caller - Jessica]

They don't know that your husband is out doing this all the time. It just doesn't make sense.

[Jamie Massey]

Oh, horrible. Well, at least I found out in the first, you know, week you didn't.

[Jen]

Waste too much time. You're right.

[Jamie Massey]

Yeah. And nothing, like, at all happened, you know, so that's good. I don't feel bad about that. The Bird Show.

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[Jamie Massey]

Acast powers the world's best podcasts. Here's a show that we recommend.

[Leah Thomas]

For centuries, colonization has fractured our relationship with the land. We've come to position ourselves outside of nature as observers and masters of it, as if it were ours to control and bend to our will. But the Earth pushes back, reminding us otherwise. I'm Leah Thomas. I'm the founder of the nonprofit Intersectional Environmentalist, and I'm excited to be returning as your host for season four of as she Rises. This season, we're exploring rewilding. We'll hear how communities are letting the land lead and reimagining what it means to truly coexist with a new natural world. Subscribe now and listen to this season of as she Rises. Wherever you get your podcast.

[Jamie Massey]

Acast helps creators launch, grow, and monetize their podcasts everywhere.

[Co-host or Friend]

Acast.

[Jamie Massey]

Com.