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.

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.

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).

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)

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.

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.

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.