The Bert Show – Vault: She Wants To Know If Her Fiancé Has Been Engaged Before

Date: December 10, 2025
Podcast Host: Pionaire Podcasting / The Bert Show Cast

Episode Overview

This episode of The Bert Show centers around a classic segment called “Cosmo Call” and a listener’s pressing relationship concern: she suspects her boyfriend of a year may have been engaged before and hasn’t told her. Fueled by Internet sleuthing, anxiety, and a need for answers, the show crew helps the listener indirectly confront her suspicions. The episode explores themes of trust, communication, and privacy in relationships—with the Bert Show’s trademark empathy and lighthearted banter.

Key Segments & Discussion Points

1. Introduction to Cosmo Call & Listener’s Dilemma

[01:19 – 04:12]

• The hosts reintroduce the “Cosmo Call,” a quirky segment where they help listeners uncover information indirectly, often with Jen posing as someone from a women’s magazine conducting a survey.
• Jen recaps the current case: a listener suspects her boyfriend Tony of hiding a previous engagement after discovering an announcement online.
  • “She came across one that has his name in it…from this other bride's town, announcing the engagement.” — Jen [03:37]
• The listener expresses concern: after a year of dating, Tony has confided about past girlfriends but never about an engagement.
  • “I just feel like he might be keeping something from me. So.” — Caller [06:12]

2. The Cosmo Call Prank & Tony’s Response

[08:06 – 09:14]

• Jen (“from Cosmo Magazine”) phones Tony under the guise of a short survey, asking subtly whether he has ever been engaged.
• Tony confidently denies ever being engaged or currently engaged.
  • “Have you ever broken off an engagement?”
  • “No.” — Tony [08:51]
  • “So are you or have you ever been engaged?”
  • “No, I’ve not been engaged.” — Tony [08:57]
• The crew and listener initially accept his answers, and the listener feels reassured.
  • “I believe him…now I feel good about it. Oh, I’m so happy.” — Caller [09:29]

3. The Shocking Update: The Truth About Tony

[10:09 – 11:55]

• The listener calls back soon after with new information: she finds photographic proof—an engagement photo—confirming Tony was, in fact, engaged to the woman in the announcement.
  • “I found a picture of them, their engagement picture. It is Tony Shaw that I am dating. And I’m very, very upset.” — Caller [10:27]
  • She describes hearing hesitation in Tony’s voice during the call, now convinced he lied.
  • She considers calling Tony’s ex or even Tony’s family but is talked down by the hosts.
    • “She’s an innocent woman.” — Shannon [11:06]
• Discussion shifts to the betrayal of trust, and Jen points out the issue is not the past engagement, but Tony’s dishonesty.
  • “It’s the fact that he’s lying to me. What else is he lying about?” — Caller [11:22]

4. Listener and Host Reactions: Advice & Empathy

[12:12 – 16:24]

• The hosts offer empathy and practical advice; Phil Turano urges calm:
  • “First of all, you need to breathe. I think you need to sleep...then this is something you need to talk with him about.” — Phil Turano [12:12]
• The panel discusses possible innocent reasons Tony might not have told her (embarrassment, desire to close a chapter) vs. reasons for concern.
• Call-ins from listeners offer varied perspectives:
  • Some say to let it go as it’s the past:
    • “I think she needs to chill out. I mean, it was in the past. He’s with you now.” — Angela [13:17]
  • Others emphasize the concern is broken trust, not the secret itself:
    • “I think that I would have a pretty big problem with it…you’re like, wait a minute. Do I not know him at all?” — Jen [13:34]
  • Real-life analogies are shared; one caller learned her boyfriend had been married and had a child—she chose to discuss it openly.
• Hosts advise against confrontation and recommend an honest, calm conversation.
  • “If you approach him and put him on the defensive, right off the bat, you’re gonna do some real big damage.” — Shannon [14:54]
  • “Cause you realize you’re gonna have to explain him why you googled him…he’s gonna…be a little leery.” — Phil Turano [15:12]
• The listener expresses gratitude for the advice and admits to feeling better.
  • “I feel so much better after this advice, and I think you’re all right.” — Caller [16:04]

5. Meta-Reflection and Show Philosophy

[16:29 – 17:28]

• The show reflects on their “role” in people’s private lives. Phil explains the difference between helping at the last resort vs. immediately intervening in raw situations.
  • “We are sometimes the last resort for them…in her situation, she hadn’t done anything at all…” — Phil Turano [17:13]

Notable Quotes & Moments

• On Trust and Past Relationships:
  “If somebody was engaged and they're for some reason keeping it secret or hasn't told you about it and you're in a serious relationship. Yeah, it is a big deal.” — Shannon [11:26]

• On Privacy and Googling Dates:
  “I think I read this in a statistic a couple of weeks ago, like, 75% of women will Google the guy that they are going out with.” — Shannon [15:26]

• On Handling Emotional Turmoil:
  “You need to breathe. I think you need to sleep. I think you need to take some time. …this is between you and your man.” — Phil Turano [12:12]

• Reality Check from Listeners:
  “You either take it, accept it, or you move on. She’s way dramatizing the whole thing.” — Kelly [14:54]

Timestamps for Key Segments

• [01:19] – Cosmo Call explanation and dilemma setup
• [04:12] – Shannon/the listener describes discovering the engagement
• [08:06] – The “Cosmo Call” to Tony
• [09:23] – Initial relief; listener believes Tony
• [10:09] – Listener calls back: new proof, emotional turn
• [12:12] – Advice from the hosts; calming down & planning next steps
• [13:14] – Caller feedback: perspectives from other listeners
• [15:26] – Discussion of online sleuthing in dating
• [16:29] – Show philosophy about getting involved in listeners’ lives

Episode Tone

• Empathetic, conversational, and candid: The hosts balance humor with genuine concern; they validate the listener's emotions while also urging perspective and a calm approach.
• Supportive but real: They don’t sugarcoat the challenges of uncovering trust issues in relationships, and they’re honest about what’s at stake.

Final Takeaways

• Past secrets, especially involving engagement or marriage, trigger strong emotions around trust.
• The Bert Show serves as a relatable, non-judgmental sounding board, but ultimately, the solution lies in honest, direct communication between partners.
• Listeners are reminded that privacy, trust, and confrontation all require care, context, and a level head.

For anyone who’s ever had doubts about a partner’s past—or Googled a date—this episode is a reminder that you’re not alone, and that the answers (and even the anxiety) are best faced together, not in isolation.