Vault: One of her two live-in boyfriends might propose

Summary

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The Bert Show - "Vault: One of her two live-in boyfriends might propose"

Air Date: June 23, 2026

Episode Overview

This episode centers around Olivia, a listener who finds herself in a highly unconventional romantic predicament—she is living with two boyfriends, neither of whom knows about the other. With Valentine's Day weekend approaching, the hosts speculate whether one (or both) might be planning a proposal. The segment dives into Olivia’s logistical and emotional juggling act, the consequences of her choices, and societal double standards around gender and dating.

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Key Discussion Points

Olivia's Situation: Two Live-In Boyfriends

• Olivia has been concurrently (and secretly) living with two men: referred to on the show as "Kennesaw dude" and "Midtown guy."
• Both men believe they are in exclusive relationships with her.
• Olivia has been with both for four months, managing to keep the relationships separate.

Valentine's Day Weekend Plans and Proposal Speculation

• The hosts have been following Olivia's story for two weeks, amping up speculation as Valentine's Day approaches.
• "Kennesaw dude" had planned a special night with a limo ride, leading the hosts to suspect a possible proposal:
  • Host [01:12]: "If he's gonna spend the money on a limo rental, then he's making it not just a special night, but an extra special night … there might be a ring involved at the end of that limo ride."
• Olivia reveals the limo was canceled due to impending snow, but the hosts warn a proposal could still be in play.
• Olivia [03:26]: "You guys planted that seed in my head … when we were on the phone, he asked me … where would you want to go for your honeymoon?"

The Challenge of Juggling Two Relationships

• Both men have expressed love to Olivia, and she reciprocates, but host skepticism abounds.
• Olivia admits the scenario is increasingly stressful:
  • Main Host [04:44]: "Aren't you exhausted? … making up lies and then having to cover for your lies … Isn't it tiring?"
  • Olivia [04:57]: "It's stressful. You know, I enjoy it, but it's totally getting stressful."
• Olivia hesitates to declare favor for either man and states she's "trying to balance and stay in both relationships as long as possible or until something presents itself to really make one better than the other."
• The hosts and Olivia discuss contingency plans if one boyfriend unexpectedly whisks her away for a trip, risking the entire charade.

Ethical Dilemmas and Double Standards

• The segment grapples openly with the morality of Olivia's actions:
  • Main Host [07:59]: "If you're moving in with somebody, that's pretty serious stuff. That's the middle layer there … There's only one place to go after that."
  • Co-host 1 [07:45]: "We've said every single time that she's cheating on both these men. We've said it every single time."
• Societal gender dynamics are debated, with hosts noting that similar behavior by a man would receive harsher judgment:
  • Main Host [07:35]: "We get emails and we get calls from women that say, you know, go ahead, get yours, girl. Get yours. If it's the other way around, guys don't ever call up and go, go, get yours, boy."
  • Co-host 2 [07:03]: "This is guy behavior."

Olivia's Defense—and Admission

• Olivia maintains she doesn't expect or require approval:
  • Olivia [08:16]: "I don't come on your show to, you know, for you to accept what I'm doing … I'm just grateful for any advice you guys have to give me because there aren't very many people that I can talk to about this."

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Notable Quotes & Memorable Moments

• Host [01:51, joking]: "Maybe there's a CZ [cubic zirconia] somewhere in that limo."
• Olivia [03:26]: "He asked me this random question, like, where would you want to go for your honeymoon?"
• Main Host [04:44]: "Aren't you exhausted? … Isn't it tiring?"
• Olivia [06:17]: "I love both guys. I really do."
• Main Host [07:59]: "Both of them, their mindset is, I'm probably gonna be with this woman for the rest of my life."
• Caller Jana [08:57]: "There are so many women out there that are great women and have trouble finding guys, and here she is over here with two of them, and it just ticks me off … One of them is going to be heartbroken, and the next girl—I feel sorry for the next girl because he's going to have such a hard time trusting women after this."
• Caller Cece [10:31]: "I've been dating seven different guys, and … you can't determine on which one you love more … You gotta do what you gotta do. Have fun, enjoy it."
• Main Host [11:35]: "If she told both guys what was going on and they decided, okay, you know what? … there's no call here."
• Main Host [12:05]: "We will talk to you on Monday morning, hopefully from Atlanta. But who knows where you'll be if this dude decides to fly you out of town."
• Olivia [12:14]: "Wish me luck, you guys."

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Timestamps for Key Segments

• 00:47 – Topic introduction; Olivia’s situation recapped
• 01:12 – Hosts speculate about possible marriage proposal
• 03:26 – Olivia recaps suspicious honeymoon conversation
• 04:44 – Hosts challenge Olivia on the stresses of her double life
• 05:38 – Olivia expresses uncertainty about choosing between the two men
• 06:06 – "Do you really love both?" debate
• 07:35 – Double standards and societal reactions discussed
• 08:57 – Caller Jana criticizes Olivia’s actions
• 10:31 – Caller Cece relates her own dating experience, differing views on fidelity
• 11:35 – Hosts discuss the difference between open communication and deceit
• 12:05 – Episode wrap-up, previewing future updates

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Tone and Style

The Bert Show crew delivers their signature blend of humor, candid judgment, and empathy. Throughout the episode, they toggle between teasing, challenging Olivia, and engaging genuine ethical debate, all while involving passionate listener reactions. Olivia remains honest, if evasive, about the emotional stakes and potential consequences.

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Summary

This highly engaging and provocative episode spotlights relationship ethics, personal honesty, and societal expectations. Olivia’s story is a rollercoaster of anticipation, secrecy, and possible heartbreak, both for herself and her unsuspecting partners. The hosts and callers offer pointed advice, frank critique, and alternative perspectives. The episode closes with a tease: will Olivia face a bombshell proposal, a romantic getaway, or the unraveling of her love triangle? Listeners are left eager for the next update.

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Transcript

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[Bluff Host]

Listen, it's the vert show.

[Main Host (possibly 'Bird')]

All right, let's get back to Olivia here. We've been talking to her for about two weeks now, and she's got an obstacle this weekend. She's juggling two different dudes.

[Co-host 1]

Yes.

[Main Host (possibly 'Bird')]

Living with two different dudes. So that's like the next step. That's a serious step.

[Co-host 1]

And this weekend is Valentine's Day, so I'm sure both men and both men do have plans, and she's got to juggle that.

[Main Host (possibly 'Bird')]

And, Jeff, what did she say last time that made us think that maybe one of these guys was going to propose this weekend?

[Co-host 2]

Well, the dude, Kennesaw dude, because that's what we call him. Right. Just midtown of Kennesaw. So Kennesaw dude was supposed to get Sunday night, and Midtown dude was supposed to have Saturday night. Right. But then Kennesaw dude snuck in with a surprise and said, hey, I'm going to get us a limo to pick you up on Saturday. And I think our theory is that if Kennesaw dude's not real, he's kind of broke. And so I think the theory is that if he's gonna spend the money on a limo rental, then he's making it not just a special night, but an extra special night. And so somebody thought there might be a ring involved at the end of that limo ride.

[Main Host (possibly 'Bird')]

Maybe there's a CZ somewhere in that limo.

[Lowe's Announcer]

Yeah.

[Olivia]

Nice.

[Main Host (possibly 'Bird')]

Hey, Olivia. Good morning.

[Olivia]

Good morning.

[Main Host (possibly 'Bird')]

How are you?

[Olivia]

Well, I'm pretty good.

[Co-host 1]

Okay.

[Olivia]

I'm still a little nervous about this weekend. Although I solved the limo problem thanks to the weather, because the snow that we have coming in. Kenneth, Hawkeye and I had a little conversation about how we don't know how the drive will do in the weather. And I could get stuck there and not be able to go to my mother's house. And that it was better to just not to plan anything driving that night.

[Co-host 1]

When Tomorrow night.

[Co-host 3]

Tomorrow night. Because it will have already snow.

[Main Host (possibly 'Bird')]

Snow and ice on the ground, though.

[Co-host 1]

Yeah, but it'll be 41 and sunny tomorrow.

[Co-host 2]

Mo is it?

[Co-host 3]

Yeah, it's 41.

[Co-host 1]

It'll be 41 and sunny tomorrow. The snow's going to be gone.

[Co-host 2]

It's going to be dangerous. Why are you trying to thwart love?

[Main Host (possibly 'Bird')]

Because he's living with love ears and not logic ears.

[Co-host 3]

That's true.

[Main Host (possibly 'Bird')]

So anything she says dead on.

[Co-host 2]

When it's.

[Co-host 3]

And everybody freaks out here.

[Co-host 2]

There's 2 inches of snow on the ground. It goes up to 41. Right. That ice. That snow turns to pure ice.

[Co-host 1]

I can't believe Daggers is actually doing this. I'm trying to help her size the snow earlier.

[Co-host 2]

I'm trying to help her.

[Co-host 1]

Okay.

[Main Host (possibly 'Bird')]

Okay. So I'm having a tough time following along here.

[Olivia]

So anyway, he has already canceled the limo.

[Co-host 3]

That was a close one.

[Main Host (possibly 'Bird')]

But that doesn't. That still doesn't avoid what might be a wedding proposal this weekend. I mean, if he. If it's a limo or not, he still may be popping the question to you.

[Olivia]

You guys planted that seed in my head, and, you know, I have not ruled that out. It does seem like a possibility. And the other night when we were on the phone, he asked me this random question, like, where would you want to go for your honeymoon?

[Main Host (possibly 'Bird')]

And you said, you mean if I get married to the Midtown guy?

[Olivia]

Very funny. No, I was. I was like, oh, no. Oh, my gosh. And I said, Hawaii. But that got me thinking that he might be planning it. You know, he might really be planning a surprise for this weekend. And Midtown guy has also been acting really excited. And so now I'm going to be spending Saturday night with a Midtown guy, and I'm worried that he is going to pop some trip on us to do it. And I'm just afraid that there's going to be something that's going to happen that's going to keep me from getting to Kennesaw guy on Sunday. Oh, no.

[Co-host 3]

He's going to be like, baby, we're going to the airport right now.

[Main Host (possibly 'Bird')]

I know we're laughing about it, but aren't you exhausted? I mean, you're exhausted, like, making up lies and then having to cover for your lies, and then the possibility of this happening on Saturday night and then Sunday. Isn't it tiring?

[Olivia]

It is. It's. It's stressful. It's. It's. You know, I enjoy it, but it's totally getting stressful.

[Co-host 3]

So what do you. I mean, what are you leaning one way or the other? Are you leaning towards Midtown guy? Like, if Midtown guy, Saturday night, says, I've booked this trip, baby, I already bought you a new bathing suit. We're on the way. Like, your bags are packed. We're going to Hawaii. Do you just throw your hands up there?

[Co-host 2]

No, she told the other guy, Hawaii. Like, midtown guy's got more money. She wants him to take her to Tahiti.

[Olivia]

Oh, right.

[Co-host 3]

They're going to Bali. Right, Right. Whatever it is. I mean, do you throw your hands up and say, okay, Midtown guy, is it?

[Olivia]

I mean, I think I'm just gonna have to wait until I'm in the moment, because right now, I'm really not leaning one way or the other. I'm leaning just towards trying to balance and trying to keep. Stay in both relationships as long as possible or until something presents itself to really make one better than the other. So that could present itself this weekend. Who knows?

[Main Host (possibly 'Bird')]

So each one of them you told us has already said that I love you to you. And she says it back, and you say it back. But do you really think that you're in love with both of these guys?

[Olivia]

I love both guys. I really do.

[Co-host 3]

Who are you more in love with?

[Main Host (possibly 'Bird')]

That's crap.

[Olivia]

Oh, that's hard.

[Co-host 2]

Her boyfriends are like her children. She has a different love for each one. She doesn't love one more than the other.

[Co-host 1]

She's not in love.

[Co-host 3]

Because when you're. Yeah. When you're dating two different people, like, at some point, somebody wins. Right? At some point, somebody.

[Main Host (possibly 'Bird')]

Or both lose.

[Co-host 1]

In that case, I think that's more. I mean, because, I mean, it's not just you're dating two guys. She's living with two men and stepped up, and you are getting off on the attention, off the espionage. You feel like you're pulling on both of them, you know? And so, yeah, I don't think that you really, truly love either one of them.

[Co-host 2]

Just for the record, this is. This is guy behavior like this.

[Main Host (possibly 'Bird')]

If it wouldn't even be accepted. If it was guy, it would be

[Co-host 2]

accepted, but it would be like, oh, I can't believe he's doing that. You're crazy. You're gonna get busted. Like, we'd be talking about how he's gonna get busted and how they're gonna catch him and how he's gonna screw up.

[Main Host (possibly 'Bird')]

The tone would be different.

[Co-host 2]

How you have to Be careful. But just because she's a girl and she's doing this to two guys, like she said. Almost said, like she's excited by it, you know, at the end of the last conversation. So now it's like, what are you doing? I can't believe you're doing it. So it's a completely different. But, like, why aren't we focusing on the fact that she could get busted

[Main Host (possibly 'Bird')]

easily and the fact that we get emails and we get calls from women that say, you know, go ahead, get yours, girl. Get yours. If it's the other way around, guys don't ever call up and go, go, get yours, boy.

[Co-host 1]

No, we've said every.

[Main Host (possibly 'Bird')]

Go get both of them.

[Co-host 1]

We've said every single time that she's cheating on both these men. We've said it every single time, and we've acknowledged every single time that what she's doing is wrong. And I don't think she won't get caught.

[Co-host 3]

They both think that they're in an exclusive relationship. If she were honest and just dating both of them, whatever.

[Main Host (possibly 'Bird')]

And both of them, their mindset is, I'm probably gonna be with this woman for the rest of my life. If you're moving in with somebody, that's pretty serious stuff. That's the middle layer there. There's only one place to go after that.

[Co-host 3]

Yeah, she's a tweener stage.

[Co-host 1]

She's using Bethy's men.

[Co-host 2]

Yeah, she's dating as a verb for her.

[Olivia]

I mean, I don't come on your show to, you know, for you to accept what I'm doing. I don't expect you to accept what I'm doing. I don't expect you to think it's right. You know, you dragged me on here in the first place, and it has

[Main Host (possibly 'Bird')]

been fun radio, theater.

[Olivia]

But, yeah, I'm just grateful for any advice you guys have to give me because there aren't very many people that I can talk to about this.

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[Co-host 3]

That's your advice? Pick what guy you want or what

[Co-host 1]

we've been saying, or if Midtown guy takes you on a trip on Saturday night, just blame it on the snow on Sunday for Kennesaw dude, because it'll be up to almost 50 degrees on Sunday, and that'll be a good excuse.

[Main Host (possibly 'Bird')]

Here's Jana. Hey, Jana. Good Morning. You're on Q100.

[Caller Jana]

Good morning.

[Main Host (possibly 'Bird')]

Hey.

[Co-host 1]

Hey.

[Caller Jana]

I love you guys. I listen to you every morning for a whole hour on the way to work.

[Main Host (possibly 'Bird')]

Thank you.

[Caller Jana]

But I am just extremely ticked off. You know, there is so many Women out there that are great women and have trouble finding guys, and here she is over here with two of them, and it just ticks me off because she's gonna. It's gonna get busted eventually, and then one of them is going to be heartbroken, and the next girl. I feel sorry for the next girl because he's going to have such a hard time trusting women after this. And it just really, really ticks me off to hear that she's doing this.

[Main Host (possibly 'Bird')]

Olivia, have you. Have you spent any time about thinking about that? Because this can't end well. I mean, you probably. One of these guys is going to get really, really hurt, or both of them are going to get really, really hurt, and if you, quote, unquote, love them. Have you spent any time thinking about the hurt that you're going to inflict once it ends badly?

[Olivia]

I have spent. I have. That has crossed my mind, yes. And it worries me because I don't want to hurt them. And so, you know, I'm going to do everything I can to end one or both relationships without them knowing that they were being deceived.

[Main Host (possibly 'Bird')]

Hey, cece, you're on Q100. Good morning.

[Caller Cece]

Hey. Question. I came in on the middle of it, but I heard majority of the key parts. So how long has she been dating both of these guys

[Main Host (possibly 'Bird')]

to hear that? Olivia?

[Olivia]

Yeah. Four months.

[Caller Cece]

Four months. Oh, my God. Come on. I'm gay. Okay, so listen, I have dated. I'm at the time in the beginning of 2010, January. I've been dating seven different guys, and I've been in a relationship with them for pretty much a little bit longer than four months. But, hey, you got to do what you got to do. Have fun, enjoy it. And, I mean, you can't determine on which one you love more because, like, one of you guys said that, you know, it's like a child. You can't. It's two different. You know, two different loves. Or, you know, you can't. You love one. One or the other, so do what you got to do. I mean, it's kind of surprising. It's kind of surprising to hear that a woman is dating two guys. Just like you guys said, It's. It's bad for a guy to do it. But

[Main Host (possibly 'Bird')]

this one's obvious.

[Co-host 1]

Yeah, it's different. I mean, you. You talk about dating seven guys, but she's living with both these guys.

[Main Host (possibly 'Bird')]

And did these guys know about each other, Cece?

[Caller Cece]

No. Well, you know what? Actually, no, I take it back. They actually do, because what I did,

[Bluff Host]

I put some Alter test.

[Caller Cece]

And I actually invited them all out. That's why this is all my friends.

[Main Host (possibly 'Bird')]

I got no brief at all with this. If she told both guys what was going on and they decided, okay, you know what? I love you so much that I'm willing to risk this and take a chance on it. There's no call here.

[Co-host 2]

I think you should tell them that for Valentine's weekend, I think you should invite them all to the same dinner. Both guys, Olivia and both guys, right in Kennesaw and Midtown.

[Main Host (possibly 'Bird')]

There's a major difference here, though. They have no idea. And they're both living with a woman that they think they're going to be with for the rest of their lives. It's totally different.

[Co-host 1]

At least Kennesaw. I'm not sure if Midtown feels that way, but Kennesaw, definitely.

[Main Host (possibly 'Bird')]

All right, Olivia, we will talk to you on Monday morning, hopefully from Atlanta. But who knows where you'll be if this dude decides to fly you out of town.

[Olivia]

Wish me luck, you guys.

[Main Host (possibly 'Bird')]

No, no. Yeah, good luck.

[Co-host 1]

Just blame it on the snow. That's right. Blame it on the snow. It's gonna be here all weekend.

[Main Host (possibly 'Bird')]

Talk to you on Monday. Okay, Bye.

[Olivia]

Bye.

[Co-host 2]

All right.

[Main Host (possibly 'Bird')]

Bye bye.

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