Vault: She's Engaged To Two Men, And Ready To Come Clean

Summary

The Bert Show (Pionaire Podcasting)

Episode: Vault: She's Engaged To Two Men, And Ready To Come Clean

Date: January 5, 2026

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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.

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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])

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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 |

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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

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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.

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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.

Transcript

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[Show Host 1]

Get it the Birch show where to even start when it comes to Ally? I mean, she emailed us about two weeks ago and we haven't been able to get to it until yesterday. And what she initially emailed for, we kind of like breezed through because the second part of the conversation with Ali is where it really, really started to get interesting.

[Show Host 2]

We thought it was just gonna be this question about her lying about her age. And then it turned into something completely different.

[Show Host 1]

She ended up being engaged to two guys at the same time and she felt so guilty she wanted to break up with one of them. And she, she suggested to do it on the radio and you'll hear throughout this replay that we're gonna do for you we tell her, you know what, this is a bad idea. Dude's gonna be totally humiliated anyway once he finds out that you're engaged to another guy. Do it in private. Do it in private. She kept saying, no, I wanna do it this morning. And was it you that had the theory on why? No, it was Jen that had the theory on why she wanted to do it on the radio.

[Show Host 2]

Well, she was kinda cowardly. I mean, she was weak and cowardly. And that's the reason why she said yes to his proposal to the second proposal in the first place, because she didn't want to make him feel bad. So we thought if she doesn't do it with us, she's not going to do it at all.

[Show Host 1]

Right.

[Show Host 2]

And so I think that's why she wanted to do it on the radio. Because we would kind of like be there to say, you know, not let her just like have a chit chat conversation.

[Show Host 1]

This was a mess. This was the better part of 90 minutes on the show yesterday. And it's all compressed down to about 12 minutes. Good morning, Allie.

[Ally (Caller/Guest)]

Good morning.

[Show Host 1]

Tell us the story of you and is this a fiance we're talking about or is it a boyfriend or.

[Ally (Caller/Guest)]

It is actually a fiance. Okay. I actually live, of course, here in Atlanta and he lives in Kansas City, Missouri. Okay, so it's been a long distance for four years.

[Show Host 1]

Tell us the second part of this whole thing.

[Ally (Caller/Guest)]

Okay, well, while dating the guy and the Kansas guy, my ex, he finds me, calls my mother's house and finds me. He finds me in contact with me. It's been like five years, five or six years. He finally gets in contact with me and you know, he's like, hey, let's go out, let's talk. And you know, he's like, I just got out of my relationship and so it's just like he loves the crap out of me. And he has proposed to me, but he doesn't know that I am engaged to get married to the Kansas guy.

[Show Host 2]

Say what? He proposed to you without like ever messing around with you or did you mess around with him?

[Ally (Caller/Guest)]

Well, yeah, I mean, he's my ex. I mean it's a past relationship, so.

[Show Host 1]

How long is it?

[Show Host 3]

But what Jen is asking is he all of a sudden proposed to you at dinner, like you messed around with him currently as his ex before he proposed?

[Ally (Caller/Guest)]

Well, no, this is a guy that has did whatever he could possibly do to track me down. So he's finally tracked me down and he's calling on a regular basis, but he does not know he Thinks that I'm not with the Kansas guy anymore.

[Show Host 1]

All right, hold on one second. How long have you been broken up with the guy that just.

[Ally (Caller/Guest)]

Oh, it's been like five years.

[Show Host 1]

Five years. He comes out of nowhere and he finds you.

[Ally (Caller/Guest)]

He finds me?

[Show Host 1]

He proposes to you?

[Ally (Caller/Guest)]

Correct. He proposes to me like two weeks after he found me.

[Show Host 1]

And you say.

[Ally (Caller/Guest)]

I say yes.

[Show Host 2]

What?

[Show Host 3]

Allie.

[Show Host 2]

Allie, he proposed to you with a ring and everything?

[Ally (Caller/Guest)]

Yes, he did. Actually. He did. And he said yes. The two weeks. I mean, you know, he was just like, oh, I love you so much and doing this and doing that for me. And it got to the point, it's just like, you know, I'm already engaged, I'm already in a relationship. But he thinks I'm not with the guy anymore. But I actually am with the Kansas guy.

[Show Host 3]

Well, the reason he thinks that Al is cause you didn't tell him other otherwise. I mean, and now you're engaged to two men. I mean, you. I guess you truly are acting your age at this point.

[Ally (Caller/Guest)]

You know, it's. It's just like I don't. This guy is so hard to tell no to without him like an out.

[Show Host 3]

Ally, you're engaged to somebody. Ellie, come on. You don't need to marry. You're not ready to be married to anybody. Because you're playing this like his boyfriends in high school. Okay, I'm going out with no one and then I'm going out with the other.

[Ally (Caller/Guest)]

Trying to play it like that. It's just the simple fact that just don't know. I mean, I don't want to be with the guy, the guy that is my ex. I don't want to.

[Show Host 3]

Then why did you say yes then?

[Show Host 1]

You're engaged to him right now, so you must be talking to him every single day.

[Ally (Caller/Guest)]

No, it's not every single day. And I'm so. I'm totally distant towards him. He doesn't. He doesn't get the point. And I want to be able to like, you know, hey, I don't love you anymore.

[Show Host 1]

I used to love you.

[Show Host 3]

Are you wearing his ring right now? Are you wearing his ring?

[Ally (Caller/Guest)]

I'm not.

[Show Host 3]

Where is it?

[Ally (Caller/Guest)]

It's at home.

[Show Host 1]

You're so funny to me. Cause you say he just doesn't get the point. Well, you said yes when he engaged to you, so what's the point?

[Show Host 3]

You have his ring.

[Ally (Caller/Guest)]

Yeah, but it's not on.

[Show Producer/Assistant]

Oh, okay.

[Show Host 3]

Oh my God. Are you kidding me?

[Ally (Caller/Guest)]

It's not on. It's really bad.

[Show Producer/Assistant]

Do you think you're one of Those people who attracts drama, do you think?

[Ally (Caller/Guest)]

I mean, it's just a simple one. If I pass there, pass by his house on the way leaving work, he's like, hey, can you stop by? I'll stop by and I'll put it on. But I'll put the ring on. But it's like when I leave, I'll take it off.

[Show Host 3]

There are plenty of 21 year olds in Atlanta right now going, are you kidding me? Like, yeah, they're a lot more mature than you, Ally. That's ridiculous.

[Show Host 1]

So, I mean, Allie, all you had to do when this guy came back and say, look, I don't want to see you. And when he proposed to you, all you had to do is say, hey, I'm seeing somebody else. I'm engaged to somebody else, I want nothing to do with you. You couldn't even do that.

[Ally (Caller/Guest)]

The guy is the type of guy, he's just so clingy. And he's clingy because you're engaged to him. No, he was clingy beforehand. It's just like if I tell him that, you know, I don't want nothing to do with you, I think he'll like wig out or something.

[Show Host 2]

I think that you like the attention.

[Ally (Caller/Guest)]

No, it's not about the attention. I can care less about the attention. It's just a simple fact. You know, he's like, I mean, as soon as he found me, he called my mom's house and my mom gave him my number.

[Show Host 2]

It's just like, you're flattered by the attention. You're flattered by the fact that he searched for weeks to find you. So you wanted to keep that attention coming. You got the long distance boyfriend. Well, he's long distance, he's far away. He hasn't given me attention in months. And I won't see him for a while and he'll never find out about it. I'll just play with this for a little while.

[Ally (Caller/Guest)]

I know, but I don't sleep with the guy. It's not about that.

[Show Host 1]

You are engaged to two men.

[Show Host 3]

Can you hear yourself? This is ridiculous.

[Ally (Caller/Guest)]

I do. I just, you know, I want to tell him that, hey, I'm engaged with the guy in Kansas. I don't want anything to do with you, just. So why stop calling?

[Show Host 2]

Why don't you say just that and.

[Ally (Caller/Guest)]

I apologize, I took the ring. I mean, you know, I want to.

[Show Producer/Assistant]

Be able to, but why don't you? You're telling us what you want to do, we're asking why you don't.

[Ally (Caller/Guest)]

Because he'll I don't. His reaction will be really crazy and. I mean, he's like, suicidal.

[Show Host 1]

Good.

[Show Host 2]

Let's call him right now then.

[Ally (Caller/Guest)]

I can't do that.

[Show Host 1]

I don't think there's anything that anybody in here or anybody in the phones is going to say to you to make you realize that you're probably not ready to be in a marriage.

[Ally (Caller/Guest)]

Well, I just. I just want. I mean, the age thing, I can, you know, tell the Kansas guy.

[Show Host 3]

No, you need to tell the Kansas guy a hell of a lot more than your age.

[Show Host 1]

Yeah, you've got a whole bunch of things going on.

[Ally (Caller/Guest)]

I know, I know that, but at least the guy here. I'm just trying to be like, you know what? I'm still engaged with the guy in Kansas.

[Show Host 1]

He doesn't know that. He is walking around today thinking he's gonna spend the rest of his life with you.

[Ally (Caller/Guest)]

That is so true.

[Show Producer/Assistant]

Yeah, it is.

[Show Host 3]

And why? Because you said yes.

[Show Host 1]

Ali, you got to take a real. You gotta look at this. Honestly, I don't know if you're capable.

[Ally (Caller/Guest)]

When are you looking at it? That's why I want to tell the. Tell the guy now that you know. Hey, I. I can't be all.

[Show Host 3]

You gotta tell them both. I wish you'd come clean to both of them and just lose them both.

[Show Producer/Assistant]

When are you gonna tell the Atlanta fiance?

[Ally (Caller/Guest)]

Like, soon.

[Show Host 3]

Like, soon.

[Ally (Caller/Guest)]

Like, like really soon.

[Show Producer/Assistant]

Like within 24 hours, within one week, within one month?

[Show Host 3]

What's too.

[Show Host 1]

No.

[Ally (Caller/Guest)]

Because I don't want to keep going on for a month or for a week or for another day.

[Show Producer/Assistant]

Are you going to tell him? But, like, by this time tomorrow, I will.

[Ally (Caller/Guest)]

I will tell him yes. Because I don't want him to keep hoping things in the future for us. And it will never be.

[Show Host 1]

I know where Jeff's going with this. He wants us to check back in with you tomorrow morning around the same time, see if you. But I wouldn't believe you.

[Ally (Caller/Guest)]

Yeah, you know, if you want. I mean, if you all have time, hell, you can call now if you want to, but it's just simple fact that I don't want to keep going. It's killing me. It's killing me inside to lead these two gentlemen on.

[Show Host 3]

I think, you know, we need to lead her on the right path. I think. You know, as Jen said earlier, I do think that we should allow Ally the opportunity to call him and tell him with us.

[Show Host 1]

You want to call him next, Allie?

[Ally (Caller/Guest)]

Well, I can for sure call the Atlanta guy.

[Show Host 3]

Okay, let's call the Atlanta guy. Then make you, you know, stand behind your word.

[Ally (Caller/Guest)]

Yeah. For once, I, I, I would love to call him. So I want to get it off my chest. It kills me every time I see him that, you know, hey, I'm just actually not being with you. I just don't want to be with you.

[Show Host 2]

Do you know it's mean, though.

[Ally (Caller/Guest)]

I mean, I know it's mean.

[Show Host 2]

It.

[Ally (Caller/Guest)]

It hurts just once. It kills me. It really kills me inside, to be honest.

[Show Host 3]

I was mean to say yes to him.

[Show Host 2]

Huh?

[Show Host 3]

We got to clean this up.

[Show Host 1]

All right. You suggested that you wanted to do this this morning.

[Ally (Caller/Guest)]

You know, I thought about it all last night and flying back into town from yesterday, it's time to do it. I can't. Can't sleep another day with that on my mind or in my heart.

[Show Host 1]

Now, you suggested that you wanted to do this on the radio. Are you sure you want to do that?

[Ally (Caller/Guest)]

Yeah, I am. Cause I don't think I could tell them face to face or without us.

[Show Host 2]

Pushing her along, too.

[Show Host 1]

I'm not. I'm advising against it.

[Ally (Caller/Guest)]

I'm actually. I want to do it because I want to get it off my chest, and I want to get it out.

[Show Host 1]

The way because, you know, like, this guy's going to feel a little humiliated right off of the bat because you're going to tell him that you're engaged to somebody else, and now you're going to do it publicly, which isn't going to help things.

[Ally (Caller/Guest)]

I know. I just want to get it off my chest. I really do.

[Show Host 1]

Okay, here's our deal. We're going to do the same way we did it last time, where we have to tell him before we put him on the radio live, that he's going to be on the radio. So the next thing you're going to hear is, Is Jeff telling him that he's gonna be on the radio, and we're not gonna use his real name. We're calling him Tom. Right. Okay. We're not gonna use his real name. Jeff will tell him what's sort of going on, and then I'll talk to him a little bit, and I'm just gonna throw it to you.

[Ally (Caller/Guest)]

Okay.

[Show Host 1]

All right. Jeff. Jeff's not exactly sure what he's doing.

[Show Producer/Assistant]

He didn't answer, so I had to ask for him.

[Show Host 1]

Okay. Jeff was huddled in the corner to where we couldn't hear him on mic. Ask for his real name, obviously. Good.

[Show Producer/Assistant]

Hey, listen, we want to. We're talking with. They do it their home with your girlfriend now. But we're using A fake name for her, so we're calling her Ally. So we want to know if we can put you on the air with her and use a fake name for you. Is that cool? You have. She called us with a question about Yalls relationship, y'.

[Show Host 1]

All.

[Show Producer/Assistant]

What. What's.

[Show Host 3]

He's evolving.

[Show Producer/Assistant]

What name? Do you have a preference as to the name you'd like to use? All right. Okay, we'll use Tom. Hold, please. There he is.

[Show Host 1]

Hi, Tom.

[Ally (Caller/Guest)]

Yes, sir.

[Show Host 1]

Hi. You sound so nice. My name's Bert, and you're on the radio right now.

[Ally (Caller/Guest)]

Okay.

[Show Host 1]

And we have Allie on with us. And I want to brace you right now. I want to tell you that the news that she's going to give you is not great news.

[Ally (Caller/Guest)]

Okay?

[Show Host 1]

All right. With that, Ally, I'll turn it on over to you.

[Ally (Caller/Guest)]

Hey. You know I really care for you, right? And it's really killing me inside that I can't continue to let this lie kill me. So you remember my ex? I told you about the Kansas guy? Remember I told you that I was engaged to him? That we broke it off? Well, we didn't break it off, and I'm still engaged to him. And it's. It's like I really care for you and. But it's just like I don't see you and I being, you know, engaged or a life down the road, because it's just not like, you know, we've been together.

[Show Host 1]

Hey. Hey, Allie. At that point, I think you just. I think it's wise to stop. Hey, Tom.

[Ally (Caller/Guest)]

Yes, sir?

[Show Host 1]

What Allie told us this morning was that when you proposed to her.

[Show Producer/Assistant]

She.

[Show Host 1]

Really has, like, this thing about saying no. She didn't want to hurt your feelings. And even though she knew in her heart it wasn't the right thing to do, she said yes. And she's kind of been living this lie that she's been regretting ever since, and she didn't know how to tell you.

[Show Host 3]

Well, and Tom also. I mean, I know it seems kind of rude to do this on morning radio, but I think that we didn't trust Allie to be honest with you without us. And I felt like you needed to know the truth. And so I'm sorry to do it in this way, but it seemed to us from Ally, that this is the only way she was gonna do it.

[Show Host 2]

Are you there?

[Ally (Caller/Guest)]

I'm still here. I just don't. I didn't know how to tell you because I've been with the Kansas guy for four years, and it's just like you did all you could possibly do find me. And I totally, really, really appreciate that. But, you know, as far as, like, the engagement goes, I just. I just don't see that, you know, later on down the road.

[Show Host 1]

So, Elliot, essentially what you're saying is you're engaged to another man and you're gonna. Right, you're gonna keep that engagement to the guy in Kansas City.

[Ally (Caller/Guest)]

Yeah. I. I'm so sorry that I. I didn't know how to tell you.

[Show Host 1]

Well, I mean, you knew that wasn't going to end well, right?

[Ally (Caller/Guest)]

I know.

[Show Host 3]

At least he knows I'm. I just. He had to know the truth.

[Show Host 1]

Did anybody catch what he said before he took off?

[Show Host 3]

I think he's just gonna go.

[Show Host 2]

I think he said, I'm gonna go.

[Show Host 1]

He's gonna go.

[Show Host 3]

Yeah.

[Show Host 1]

You know, I mean, you knew it couldn't end well. I mean, you were gonna. You had to hurt him either in the beginning or you had to hurt him at the end.

[Ally (Caller/Guest)]

Right. I totally understand that now you gotta.

[Show Host 2]

Fess up to Kansas City guy.

[Show Producer/Assistant]

Tell him you're really 12.

[Show Host 3]

Well, I mean, yeah, I think you gotta be honest all the way around. Ally, you're starting your Kansas City thing based on lies. I think you need to be honest with everybody and just.

[Show Host 1]

Yeah. So do you go ahead and do you tell the Kansas City guy that you said yes to an engagement from a guy here in Atlanta or not?

[Ally (Caller/Guest)]

You know, I'm gonna have to like, clear it all up with. And I don't think I need to be in a relationship. I mean, it's not. Maybe I just need to single life because I obviously can't break the news to no one.

[Show Host 1]

Ellie, you had to see some of this coming.

[Ally (Caller/Guest)]

Yeah, I know, I know.

[Show Host 1]

We gotta go.

[Ally (Caller/Guest)]

I've been. I'll just have to break the news and just clear out everything. Good.

[Show Host 1]

I think it's a great idea.

[Ally (Caller/Guest)]

Yeah.

[Show Host 1]

Start over.

[Show Host 2]

Clean slate.

[Ally (Caller/Guest)]

Yeah, that's exactly what I'm going to do.

[Show Host 3]

Well, good luck, Allie.

[Ally (Caller/Guest)]

All right. Thank you so much.

[Show Producer/Assistant]

Bye bye.

[Ally (Caller/Guest)]

Bye.

[Show Host 1]

Bye. Get it the Bird show.

[Verizon Announcer]

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