The Bert Show

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

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.

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.

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.” |

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

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.