The Bert Show (Pionaire Podcasting)
Episode: Vault: She's Engaged To Two Men, And Ready To Come Clean
Date: January 5, 2026
Overview
This episode centers on a dramatic listener dilemma involving "Allie," who confesses to being engaged to two men at once. The show explores her tangled relationships, the reasons behind her decisions, and ultimately supports her as she comes clean to one of her fiancés live on air. The hosts offer candid, sometimes tough love, advice, while questioning Allie’s readiness for marriage and discussing the broader implications of honesty in relationships.
Key Discussion Points & Insights
1. Introduction to Allie’s Situation
-
[01:32–02:45]
- The hosts reveal they initially thought Allie was writing in about lying about her age, but uncovered a much bigger issue.
- Allie is engaged to two men: one, a long-distance fiancé in Kansas City, and the other, an ex who recently re-entered her life and proposed.
- Hosts debate the ethics and emotional fallout of confronting personal drama on air vs. privately.
Quote:
“She ended up being engaged to two guys at the same time, and… suggested to do it on the radio… We tell her, you know what, this is a bad idea. Dude’s gonna be totally humiliated.” — Host 1 ([01:58])
2. How the Double Engagement Happened
-
[02:55–05:00]
- Allie explains her long-term long-distance relationship and reconnection with her ex, who tracked her down and quickly proposed.
- She accepted both proposals but kept each man in the dark about the other.
- The panel presses Allie on why she agreed to the second proposal when she wasn’t interested.
Quote:
“He proposed to me like two weeks after he found me.” — Allie ([04:32])“You must be talking to him every single day…” — Host 1 ([05:39])
“No, it’s not every single day. I’m so… distant.” — Allie*
3. Confrontation and Candid Advice
-
[05:06–07:07]
- Allie admits to hiding her real relationship status and trying to avoid hurting anyone’s feelings.
- The hosts challenge her maturity and honesty, suggesting she isn’t ready for any marriage.
- Allie claims she fears the ex-fiancé’s reaction if she tells the truth.
Quote:
“There are plenty of 21 year olds in Atlanta right now going, are you kidding me?... They’re a lot more mature than you, Allie. That’s ridiculous.” — Host 3 ([06:32])“I think that you like the attention.” — Host 2 ([07:05])
“No, it’s not about the attention…” — Allie*
4. The Plan: Coming Clean Live On Air
-
[08:31–11:20]
- Allie agrees she needs to end things, and the hosts urge her to stop stringing both men along.
- The debate continues: Should she break up in private, or is radio intervention the only way?
- Allie insists on doing it live, admitting she lacks the courage otherwise.
Quote:
“I want to do it because I want to get it off my chest… I don’t think I could tell them face to face or without us.” — Allie ([10:55])
5. The Live Breakup
-
[12:45–15:54]
- The show contacts "Tom" (a pseudonym for privacy), the Atlanta fiancé.
- Allie reveals her ongoing engagement to the Kansas City man and calls off their engagement.
- Tom is mostly silent, reportedly only saying, “I’m gonna go,” before hanging up.
Memorable Moment:
“Remember my ex? I told you about the Kansas guy?... Well, we didn’t break it off, and I’m still engaged to him.” — Allie ([13:10])Host’s Reflection:
“We didn’t trust Allie to be honest with you without us. …it seemed to us… this is the only way she was gonna do it.” — Host 3 ([14:30])
6. Aftermath and Reflection
-
[15:26–17:02]
- The hosts encourage Allie to also come clean to the Kansas City fiancé.
- Allie realizes she may not be ready for any relationship and contemplates starting over.
Quote:
“Maybe I just need the single life because I obviously can’t break the news to no one.” — Allie ([16:29])“Start over.” — Host 1
“Clean slate.” — Host 2
“Yeah, that’s exactly what I’m going to do.” — Allie ([17:02])
Notable Quotes & Memorable Moments
| Timestamp | Quote | Attribution | |-----------|------------------------------------------------------------------------------------------|---------------| | 01:58 | “She ended up being engaged to two guys at the same time… she wanted to do it on the radio. We tell her… this is a bad idea.” | Host 1 | | 04:32 | “He proposes to me like two weeks after he found me.” | Allie | | 06:32 | “There are plenty of 21 year olds in Atlanta right now going, are you kidding me?... They’re a lot more mature than you, Allie. That’s ridiculous.” | Host 3 | | 07:05 | “I think that you like the attention.” | Host 2 | | 10:55 | “I want to do it because I want to get it off my chest… I don’t think I could tell them face to face or without us.” | Allie | | 13:10 | “Remember my ex? I told you about the Kansas guy?... Well, we didn’t break it off, and I’m still engaged to him.” | Allie | | 14:30 | “We didn’t trust Allie to be honest with you without us… this is the only way she was gonna do it.” | Host 3 | | 16:29 | “Maybe I just need the single life because I obviously can’t break the news to no one.” | Allie | | 17:02 | “Start over.” / “Clean slate.” / “Yeah, that’s exactly what I’m going to do.” | Hosts 1, 2, Allie |
Important Timestamps
- 01:32: Hosts introduce Allie’s email and storyline evolution
- 03:00: Allie details long-distance relationship and ex’s re-entry
- 04:32: Allie explains accepting her ex’s proposal
- 05:53: Allie describes how she juggles both engagements
- 07:05: Hosts confront Allie about her motivations
- 10:55: Allie decides to come clean on air
- 12:45: The breakup call with “Tom” begins
- 13:10: Allie finally confesses the truth to Tom
- 14:30: Hosts explain their rationale for facilitating the call
- 16:29: Allie considers taking a break from relationships
- 17:02: Episode wraps with Allie’s resolve to start over
Tone and Style
The episode maintains The Bert Show’s signature mix of humor, honesty, and empathy. The hosts are unflinching in their critiques—calling out immaturity and avoidance—while still offering Allie the support to do the right thing. The mood shifts from exasperation to encouragement as the drama unfolds, keeping listeners engaged with candid commentary and emotional realness.
For listeners new to the episode, this is an intense, real-life relationship saga that blends messy drama with the tough love and support The Bert Show is known for.