Vault: 2nd Date Update - Mike & Missy

Summary

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The Bert Show: Vault - 2nd Date Update – Mike & Missy

Date: October 29, 2025
Hosts: Bert, Jeff Dollar, (Caller: Missy, Date: Mike)
Podcast Theme: Morning radio show bringing real, funny and authentic stories—this episode features a “2nd Date Update,” tackling listener drama from the dating trenches.

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Overview

This episode dives into The Bert Show’s classic “2nd Date Update” segment. Missy, a listener, calls in seeking clarity after a promising first date with her coworker Mike fizzled out—despite months of workplace flirtation and an enjoyable night out. The cast brings both parties together on-air for an honest conversation to get to the bottom of the romantic cold shoulder, offering listeners both drama and relatable awkwardness.

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Key Discussion Points & Insights

1. Setup and Backstory

• Missy’s Call-in:

  • Missy shares the story of months-long mutual workplace flirting with Mike, culminating in their first official date (02:26).
  • The date was carefully planned: dinner at an Italian restaurant (Soto) and drinks at Highland Tap. Missy describes it as "wonderful" but is baffled when Mike acts distant and cold at work afterwards (02:29–02:47).

• Details of the Date:

  • Flirty buildup lasted the entire nine months they've worked together (02:55).
  • The evening started at around 7 pm and lasted until after midnight. After drinks, they went back to Missy’s apartment for some intimate but not extensive make-out time (03:32–03:48).
  • Missy recounts: “He came up to my apartment. We had, like, a last drink, and we were sitting there and, you know, making out on the couch, doing whatever, and then he leaves. Like a normal date would end where you assume everything's going okay.” (03:53)

2. The Hosts’ Probing

• Bert and co-host Jeff Dollar clarify: was the date too tame/did it end awkwardly?
  • Missy insists there was no pressure or awkwardness; the night ended naturally because they both had work the next day (04:29).
  • Duration of the date was about six hours: “7 to 1am. That’s a lot.” (04:56)

3. On-Air Confrontation: Mike Joins the Call

• Bert warns listeners: these confrontations get honest, even painfully so (05:02).
• Mike is aware something is up: “A friend of mine just called me about, I don’t know, 15, 10 minutes ago or something like that.” (05:46)

4. Mike’s Side of the Story

• Mike explains that while he enjoys Missy's company and finds her attractive, she talked about work for most of the date: “All she wanted to talk about was work…speculating on who makes what, and it’s just the kind of stuff, obviously, that I don’t want to talk about. Certainly out of date. I socialize to get away from work.” (06:23–06:40)

  Notable Quote

  • Mike: “I socialize to get away from work. And that was basically all she talked about.” (06:38)

• Missy seems surprised but admits maybe she talked “a few questions or said a few things,” but didn’t think it was so significant (07:07).

5. Prospects for Another Date

• Bert asks if they could give it another shot—with a “no talking about work” rule.

• Mike’s reservations go deeper: he realizes it might not be wise to date a co-worker because “inevitably that kind of stuff is going to come up.” He expresses doubts about mixing work and romance, calling it “not a healthy mix.” (07:38–08:11)

  Notable Quote

  • Mike: “After that I kind of realized maybe it’s not, you know, such a good thing to date someone that you work with really closely…not really sure if it’s such a good idea to go out again.” (07:38–08:11)

6. Resolution and Closing

• Missy accepts Mike’s explanation with brief, disappointed acknowledgement (08:11).
• The hosts thank Mike for his honesty and wrap up with friendly, if awkward, goodbyes (08:12–08:23).

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Notable Quotes & Memorable Moments

• Missy, on her confusion:
  • “Yeah. I don’t understand. Everything was so great, and then just, like, a complete total different change back at work.” (03:26)
• Jeff Dollar:
  • “This is what we call the comfortable moment of the bird show.” (06:12)
• Mike, on workplace romance:
  • “I just really, you know, don’t like talking about work outside of work, basically. And, you know, I leave it all there…” (07:25)
• Mike, on the root cause:
  • “It's not a healthy mix…I'm not really sure if it’s such a good idea to go out again.” (08:11)

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Key Timestamps for Important Segments

• [02:01] — Bert introduces the 2nd Date Update and brings in Missy.
• [02:29] — Missy summarizes her story and the “great date.”
• [03:12] — Missy details the date’s setting and events.
• [03:35] — Missy describes what happened after the date.
• [04:56] — Duration of the date: “7 to 1am. That’s a lot.”
• [05:13] — Transition to call with Mike.
• [05:46] — Mike answers, reveals he suspected the call.
• [06:23] — Mike shares why he’s not interested: too much work talk.
• [07:38] — Mike expresses reservations about dating coworkers.
• [08:11] — Final wrap-up and sign-off from both parties.

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Episode Takeaways

• Dating coworkers can easily blur personal/professional boundaries and lead to unforeseen consequences.
• Communication gaps—how one person perceives conversation topics (Missy’s casual workplace talk) can be off-putting to another (Mike’s desire to “leave work at work”).
• Honest confrontation, live and on air, produces both drama and real-life insights about boundaries, social norms, and dating pitfalls.

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For listeners who missed this episode, “2nd Date Update: Mike & Missy” packs the awkwardness, humor, and relatability you’d expect—along with real advice on why workplace flings sometimes fall flat.

Transcript

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[Bert (Host of The Bird Show)]

Get it the Bird show we have all been here before. You have a great first date. You spend six or seven Hours on it. And you're just waiting for the second date, waiting for the phone to ring so you can set up that second date, and it just doesn't happen. Well, when that happens to one of the Burksho listeners, what they do is they call us up, and we call the guy on the air and ask him why there's been no second date. We call that second date update. Morning, Missy.

[Missy (Caller)]

Good morning.

[Bert (Host of The Bird Show)]

All right, Missy, tell us about the great first date you had with.

[Missy (Caller)]

It was Mike. Yeah, he's just this really great guy. We actually. We are working together. I've dropped quite a few hints, and the guy finally asks me out. So it was just this wonderful date that we had, and I don't understand. You know, since then, he's just totally given me the cold shoulder at work.

[Bert (Host of The Bird Show)]

Now, how long have you guys been working together?

[Missy (Caller)]

Gosh, we've been working together for about nine months.

[Bert (Host of The Bird Show)]

And how long has this whole flirty, flirty thing been going on?

[Missy (Caller)]

This has been. Well, originally starting about when he first started working there, and we've both been working there for about nine months. So it's been like this long, overdrawn thing where, you know, built up to flirting. He finally asked me out, we went out, and everything was great.

[Bert (Host of The Bird Show)]

Where'd you guys go? What'd you do?

[Missy (Caller)]

Oh, man. He took me down to Soto. Soto took me over. We went to Highland Tap for martinis, and we. Gosh, for a couple of hours we were there.

[Bert (Host of The Bird Show)]

This guy did it right. Takes you to a nice Italian place, gets it for the best martini in the town. Okay.

[Missy (Caller)]

Yeah. I don't understand. Everything was so great, and then just, like, a complete total different change back at work.

[Jeff Dollar (Co-host of The Bird Show)]

Did you guys go back home after Highland Tap?

[Missy (Caller)]

Yeah, we actually, you know, we made out for a little while. He came back up to my apartment, and, you know, it wasn't too extensive, but it was really cool. I just can't figure it out.

[Bert (Host of The Bird Show)]

All right, so a little intimacy there, but nothing, like over the top.

[Missy (Caller)]

Yeah.

[Bert (Host of The Bird Show)]

Yeah.

[Hannah Berner]

I'm curious.

[Bert (Host of The Bird Show)]

How did the date end? Like, did it seem like it was on a good note?

[Missy (Caller)]

Yeah, I mean, he came up to my apartment. We had, like, a last drink, and we were sitting there and, you know, making out on the couch, doing whatever, you know, and then he leaves. Like a normal date would end where you assume everything's going okay.

[Bert (Host of The Bird Show)]

What was. How. What was the approach to leave the apartment was, I've got an early day tomorrow, was it?

[Missy (Caller)]

No, it was just kind of like, you know, it was.

[Bert (Host of The Bird Show)]

Night was over.

[Missy (Caller)]

Night was over 11 in the morning, we both had to work the next day. It wasn't, you know.

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[Hannah Berner]

I mean, the reason I was asking about how the date ended because I'm.

[Bert (Host of The Bird Show)]

Just wondering if he was disappointed it didn't go further.

[Missy (Caller)]

No, I really, to be honest with you, I don't think so because there was no really pressure there from either side. It was just. It was time to be over. I think that was kind of how we both felt about it.

[Jeff Dollar (Co-host of The Bird Show)]

Okay, what from, from the time he. Did he pick you up or did you guys meet at the restaurant or how'd that work?

[Missy (Caller)]

We actually met at the restaurant.

[Jeff Dollar (Co-host of The Bird Show)]

Okay. From the time you guys met at the restaurant to the time you guys finished necking and he headed home. What's. What are we looking at for a total date time frame there?

[Missy (Caller)]

Oh, Gosh, I'd say 7 to 1am That's a lot.

[Bert (Host of The Bird Show)]

And Missy, I gotta be honest with you. We totally tr. I mean, we will pressure this guy to give you total honesty and we won't let him off the phone until he does. So sometimes it gets painful. All right, Missy, hold on one second.

[Missy (Caller)]

All right, Missy.

[Mike (Date of Missy)]

Yes, you're there.

[Bert (Host of The Bird Show)]

Okay, cool. We're gonna beg him for total honesty with this thing. Okay.

[Missy (Caller)]

Okay. All right, I want you to.

[Bert (Host of The Bird Show)]

You know these things don't end well, right? It's very rare that they end well.

[Mike (Date of Missy)]

Hello?

[Bert (Host of The Bird Show)]

Hi, is Mike around, please?

[Mike (Date of Missy)]

Yes, he.

[Bert (Host of The Bird Show)]

Hi, Mike, this is bert calling from Q100. We're on the air right now. I'm with Melissa Carter and Jeff Dollar and we also. We have one of your co workers on the phone.

[Mike (Date of Missy)]

Okay. Yeah, and you guys are gonna call. Actually.

[Bert (Host of The Bird Show)]

How'd you know that?

[Mike (Date of Missy)]

A friend of mine just called me about, I don't know, 15, 10 minutes ago or something like that.

[Bert (Host of The Bird Show)]

Alright, so you know what's going on here?

[Mike (Date of Missy)]

Kind of, but not really sure exactly what the point of it.

[Bert (Host of The Bird Show)]

Hey, Missy.

[Missy (Caller)]

Yeah.

[Bert (Host of The Bird Show)]

You want to go ahead and tell Mike why we're calling?

[Missy (Caller)]

I was actually wondering, you know, we went out, we had a great date and I don't understand, like it didn't go anywhere from there.

[Mike (Date of Missy)]

Yeah.

[Jeff Dollar (Co-host of The Bird Show)]

This is what we call the comfortable moment of the bird show.

[Mike (Date of Missy)]

Yeah, I know.

[Bert (Host of The Bird Show)]

And now she's.

[Mike (Date of Missy)]

She's opened up embarrassed.

[Bert (Host of The Bird Show)]

She's opened herself up here too, Mike. She wants total honesty on why there's been no second date.

[Mike (Date of Missy)]

I guess basically what it boils down to is, you know, it was really fun and I think she's really nice and she's got a nice personality and everything, and she's good looking, too. But basically, I mean, all she wanted to talk about was work, you know, and it was just always about work. She was talking about, you know, my friends who I work with and have worked with for a while and, you know, speculating on who makes what. And it's just the kind of stuff, obviously that I don't want to talk about. Certainly out of date. You know, I socialize to get away from work. And that was basically all that she talked about.

[Bert (Host of The Bird Show)]

Missy. Did that make any sense to you? Just a little too work, you know.

[Missy (Caller)]

I don't really think I was talking about work that much, was I? I mean, yeah, kind of.

[Mike (Date of Missy)]

Yeah, you were.

[Missy (Caller)]

I don't really recall, but I guess maybe I did ask a few questions or say a few things, but I didn't think it was like that much to where it would bother you.

[Mike (Date of Missy)]

Yeah, I just really, you know, don't like talking about work outside of work, basically. And, you know, I leave. I leave it all there and.

[Bert (Host of The Bird Show)]

Well, would it be possible for you guys to go out again? And if so, then she'd promise not to talk about work?

[Mike (Date of Missy)]

I'd like to if I thought it would, you know, be the right thing to do. But, you know, after that I kind of realized maybe it's not, you know, such a good thing to date someone that you work with really closely and, you know, inevitably that kind of stuff is going to come up. You're going to talk about it, you know, I mean, you. You do talk about your problems with your significant other, so. And they tend to be work related. And I just don't, you know, I don't know if it's such a healthy mix. I'm not really sure if it's such a good idea to go out again.

[Missy (Caller)]

Well, okay.

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[Bert (Host of The Bird Show)]

You just kind of realize now that, you know, maybe it's not a good idea to start dating somebody from work.

[Missy (Caller)]

All right, all right.

[Bert (Host of The Bird Show)]

Hey, we're gonna let you go, Mike. Thanks for being so honest.

[Hannah Berner]

Appreciate it.

[Mike (Date of Missy)]

Okay, man, thanks.

[Bert (Host of The Bird Show)]

Take care.

[Mike (Date of Missy)]

I'll see you later.

[Bert (Host of The Bird Show)]

Get it the bird show.

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[Hannah Berner]

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[Hannah Berner]

Same. They're so light and so comfy. And if it's not comfortable, I'm not wearing it.

[Paige Desorbo]

And the bras. Soft, supportive and actually breathable.

[Hannah Berner]

Yes. Lord knows the girls need to breathe. Also, I need my PJs to breathe and be buttery, soft and stretchy enough for my dramatic tossing and turning at night. That's why I live in my Tommy John pajamas.

[Paige Desorbo]

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[Hannah Berner]

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