Vault: 2nd Date Update - Dylan & Maggie

Summary

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The Bert Show

Episode: Vault: 2nd Date Update – Dylan & Maggie
Date: October 31, 2025

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Episode Overview

This episode of The Bert Show revisits a particularly memorable “2nd Date Update” involving Dylan Carbello and Maggie. The segment explores the fallout after a seemingly successful first date, followed by Dylan’s relentless attempts to contact Maggie—which border on obsessive. The hosts dissect the situation with humor and candid advice, letting Maggie tell her side and cautioning listeners about overbearing dating behavior.

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Key Discussion Points & Insights

1. Dylan’s Overzealous Follow-Up

• The Setup:

  • Dylan emails the show just 15 hours after a Friday night date, puzzled by Maggie’s lack of response.
  • He attempts to come on air but Maggie warns him off, threatening never to speak to him again if he does.

• Dylan’s Call Pattern:

  • Despite Maggie’s warning, he calls her persistently over the weekend—multiple times Saturday (morning and night), Sunday morning, and even again Monday before she joins the show.
  • The hosts react incredulously to the number and persistence of these calls.

  "He called me Saturday morning. What are you doing?" – Maggie (04:12)
  "17 calls? That includes the hang ups." – Podcast Host 3 (06:43)

2. Maggie’s Perspective

• Her Account of the Date:

  • Maggie emphasizes she enjoyed the date and would’ve been interested in a second—if Dylan hadn’t overwhelmed her with calls.
  • She describes how each call grew more intrusive, from innocent check-ins to prying about her social plans.

  "We had a great time last night. Don't push it. Don't wreck it, you know?" – Maggie (04:23)

• Her Red Flags:

  • Maggie mentions hang-ups and unsolicited calls, escalating to what she jokingly refers to as “stalker mentality.”
  • She laments how Dylan’s excessive attention ruined any potential.

  "Oh, my God. I don't know if I need to change my phone number or stalker mentality kind of thing, but if Dylan Carbello calls you, run for your lives, ladies." – Maggie (04:49)
  “Dylan Carbello. Ladies, run.” – Maggie (07:09)

3. The Hosts Weigh In

• They react with humor but firmly side with Maggie, warning listeners about the dangers of over-pursuing someone after a first date.

• The hosts call out the intensity as a universal “don’t” in dating, with some chuckling at the spectacle but expressing sincerity about respecting boundaries.

  “Some guys just don’t know how to take no for an answer. And we found out in this second date update that Dylan Carbello is one of those guys.” – Podcast Host 3 (02:17)
  “Essentially what you have done is basically are the post office. And you’ve just put his picture up on the post office wall.” – Podcast Host 3 (05:13)

4. Dylan’s No-Show

• Despite being the focus, Dylan’s absence is a running joke and a statement—he won’t come on air, possibly fearing Maggie’s (and now a larger audience’s) reaction.

• The show ends with light-hearted warnings and gratitude to Maggie for sharing her story.

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Notable Quotes & Memorable Moments

| Timestamp | Speaker | Quote | |-----------|---------------------|---------------------------------------------------------------------------------------| | 04:49 | Maggie | “Oh, my God. I don't know if I need to change my phone number or stalker mentality kind of thing, but if Dylan Carbello calls you, run for your lives, ladies.” | | 06:43 | Podcast Host 3 | “17 calls? That includes the hang ups. 17.” | | 06:08 | Maggie | “I have no problem with the call the next morning. I really don't, however... don’t sit there and ask me to go through my itinerary as to what I’m going to do today and get weird about it.” | | 05:13 | Podcast Host 3 | "Essentially what you have done is basically are the post office. And you’ve just put his picture up on the post office wall."| | 07:09 | Maggie | “Dylan Carbello. Ladies, run.” |

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Timestamps for Key Segments

• [02:17] – Introduction to Dylan’s persistent behavior
• [03:34] – Maggie joins the call and begins her account
• [04:09] – Details of the call barrage begin
• [04:49] – Maggie voices her frustration and gives her warning
• [06:08] – Maggie explains what was reasonable versus intrusive
• [06:43] – The host tallies up the 17 calls
• [07:09] – Maggie delivers her final warning to listeners

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Conclusion

This “2nd Date Update” episode is a classic cautionary dating tale—funny but filled with real-life lessons on boundaries, persistence, and respecting signals. Maggie’s candid humor and the hosts’ supportive banter make the awkward saga memorable and instructive, reinforcing that sometimes, less is truly more.

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Transcript

[Jeff Bridges]

Morning Zoe. Got donuts.

[Dana]

Jeff Bridges why are you still living above our garage?

[Jeff Bridges]

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[Dana]

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[Podcast Host 1]

Nice.

[Dana]

J free.

[Podcast Host 2]

You heard them.

[Jeff Bridges]

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[Dana]

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[Podcast Host 1]

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[Jeff Bridges]

It's the vert show.

[Podcast Host 3]

Some guys just don't know how to take no for an answer. And we found out in this second date update that Dylan Carbello is one of those guys.

[Podcast Host 2]

This guy emailed me on about 2 in the afternoon and he said, I went out with this girl, I had a great date. Gave me all the details needed. Made it sound like a great second date update. Well, the interesting part of it was the date that he was referring to ended at midnight the night before. So he wanted to know why she wasn't calling him back 15 hours after the date.

[Podcast Host 3]

Oh, man. What's this dude's name?

[Podcast Host 2]

The guy's name is Dylan.

[Dana]

And how many times had Dylan called her?

[Podcast Host 2]

Well, Dylan called her so many times, he actually already spoke to her this morning before he was scheduled to go.

[Podcast Host 3]

On with us because he kept calling.

[Podcast Host 2]

And calling and calling, and she said, you go on the air, I will never speak to you again. So he won't. Come on.

[Podcast Host 3]

Let me tell you something. Anyway, she wasn't gonna talk to him. Anyway.

[Podcast Host 2]

Now, hold on a minute. After she got off the phone with him, she called us and left a message on my voicemail and said, I told him that I wouldn't do this, but I'll still go on. So I was just about to call our backup second date update when I got her message.

[Podcast Host 3]

Oh, really?

[Podcast Host 2]

She will go on the phone. Wait until you hear how many times this guy called her since. Keep in mind, the date ended Friday at midnight.

[Podcast Host 3]

Hey, Maggie.

[Maggie]

Good morning.

[Podcast Host 3]

How are you today?

[Maggie]

Oh, I'm just fine. And you?

[Podcast Host 3]

Oh, we're doing just great.

[Maggie]

You know what? Let me clear something up for you, okay? His name is just not Dylan. It's Dylan Carbello.

[Advertisement Voice]

Dylan.

[Maggie]

And I want everybody to know who Dylan Carbello is, okay?

[Podcast Host 3]

Why? What happened?

[Maggie]

Okay, we went out on the date Friday night. We went to some Italian restaurant. Remember what it was? We had a great time. We really did. And I would have gone out with him again. I had a lot of fun and everything was cool and great. He called me Saturday morning. What are you doing?

[Podcast Host 2]

What time? How long? The date ended at midnight. What time did he call you on Saturday?

[Maggie]

10Am Saturday morning. What are you doing?

[Podcast Host 2]

Did you speak to him on Saturday morning or did he leave a message? No.

[Maggie]

Dylan Carbello. I spoke with him Saturday morning. I went out and ran errands. Had a bunch of hang ups on my phone by the time I got home. Oh, yeah, he called again Saturday night. I spoke with Dylan Carbello. And it's another one of those, what are you doing tonight? You know, that kind of thing. And I'm just like, we had a great time last night. Don't push it. Don't wreck it, you know?

[Podcast Host 2]

How many calls total did he make?

[Maggie]

Oh, wait, I'm not done yet.

[Podcast Host 3]

Oh, there's more.

[Maggie]

Yes, yes. So he understood. He's sorry. The whole thing. Sunday morning, 8:00am oh, man, let it go. Do you want to go to Sunday brunch? Oh, my God. I don't know if I need to change my phone number or stalker mentality kind of thing, but if Dylan Carbello calls you, run for your lives, ladies.

[Podcast Host 3]

Well, essentially what you have done is basically are the post office. And you've just put his picture up on the post office wall.

[Maggie]

I'm telling you. And that was not the only time he called me Sunday. And then this morning, before I spoke with you guys, Dylan Carbello calls me again.

[Dana]

It's 7:22 in the morning. What time did he call you?

[Maggie]

Early. I couldn't even see the clock. My eyes weren't focused and he was all excited and he's like, oh, my God, I'm so. I'm like, oh, dude. You know, I would have gone out with you again, but you are just totally over the line on this.

[Podcast Host 2]

Now, Maggie, let me ask you a question, because let's say that your date on Friday night was beyond good. Let's say it was exciting.

[Podcast Host 1]

Excuse me?

[Maggie]

With Dylan Carbello.

[Podcast Host 2]

Let's say it was exceptional. Let's say that this was like you walked away from that dinner thinking, this might be the guy that I will marry and spend the rest of my life with. Is there any chance at all that you would have appreciated the phone calls that he made?

[Maggie]

I have no problem with the call the next morning. I really don't, however. But don't sit there and ask me to go through my itinerary as to what I'm going to do today and get weird about it, about meeting friends for. Well, who?

[Podcast Host 3]

And Dylan won't come on with us.

[Podcast Host 2]

He won't come on any of this. He won't come out. We can call him again.

[Maggie]

You mean Dylan Carbello?

[Podcast Host 2]

Now, let me.

[Dana]

I thought the reason he wouldn't come on is because he didn't want to make Maggie mad.

[Maggie]

You mean Dylan Carbello?

[Podcast Host 2]

If you count every hang up that you Got over the weekend as a call from him. How many calls do you think you got from from Saturday morning to this morning?

[Maggie]

17.

[Podcast Host 3]

17?

[Podcast Host 1]

Whoa.

[Podcast Host 3]

That includes the hang ups. 17.

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[Jeff Bridges]

Freak.

[Maggie]

There were hang up calls in there.

[Podcast Host 3]

And he must have an explanation on why he called you 17 times.

[Dana]

Do you have caller ID?

[Maggie]

Yes.

[Dana]

Okay, so you know that it was in fact Dylan calling you and hanging up.

[Maggie]

Mm.

[Podcast Host 3]

All right, well, he's not coming on with us, so this is pretty much done.

[Maggie]

Okay.

[Podcast Host 3]

I don't think you'll be getting any calls from Dylan Carbello.

[Maggie]

All right, well, thank you very much.

[Jeff Bridges]

Take care.

[Maggie]

Dylan Carbello. Ladies, run.

[Jeff Bridges]

It's the Birch Show. Morning, Zoe. Got donuts.

[Dana]

Jeff Bridges, why are you still living above our garage?

[Jeff Bridges]

Well, I dig the mattress and I want to be in a T mobile commercial like you. Teach me. So, Dana.

[Dana]

Oh, no, I'm not really prepared. I couldn't possibly at t mobile get the new iPhone 17 Pro on them. It's designed to be the most powerful iPhone yet and has the ultimate pro camera system.

[Jeff Bridges]

Wow, impressive. Let me try. T Mobile is the best place to get iPhone 17 Pro because they've got the best.

[Advertisement Voice]

Nice.

[Dana]

Jeffrey, you heard them.

[Jeff Bridges]

T Mobile is the best place to.

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[Jeff Bridges]

So what are we having for launch?

[Dana]

Dude, my work here is done.

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