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

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.

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]

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]

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]

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.

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.