Vault: She's double-booked on Valentine's Day

Summary

The Bert Show: Vault — "She's double-booked on Valentine's Day"

Original Air Date: June 22, 2026
Featured Cast: Bert (Lead Host), Kristin, Abby, Cassie, Tommy, Olivia (caller), and various listeners

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Episode Overview

In this lively and candid segment, The Bert Show reconnects with Olivia, a previous caller who stirred up interest when she revealed she was juggling two different romantic relationships—living part-time at two places with two separate boyfriends in Atlanta. As Valentine's Day approaches, Olivia turns to the show for advice: both boyfriends expect to spend the romantic holiday with her, and she's running out of excuses and mental bandwidth to keep her secret life straight. The hosts and listeners dive into the ethics, logistics, and drama of Olivia's "double-booked" situation, blending humor, curiosity, concern, and judgment.

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Key Discussion Points & Insights

1. Olivia’s Situation Revisited

• Background Recap: Two weeks prior, Olivia moved in (partially) with both "Kennesaw Guy" and "Midtown Guy," managing to keep each relationship separate by telling them her mother needs her support during an emotional divorce.
  • Quote: “I spent the night with Kennesaw guy on Saturday night, and then Sunday, I went back to my apartment. Midtown guy came over.” — Olivia (01:12)

2. Valentine’s Day Dilemma

• Olivia faces a scheduling crisis: both men expect her time on Valentine’s Day, and each has planned "special" events.
  • She tells Midtown Guy she’ll spend Saturday with him due to "work" on Monday (and to be with her mother on Valentine's Day).
  • She tells Kennesaw Guy she’ll be at her mom’s Saturday and with him on Valentine's evening.
  • Kennesaw Guy then surprises Olivia with a big gesture: a limo for Saturday night—creating an overlap in plans.
  • Quote: “He can't afford a limo. So this is a... this is like a really big deal.” — Olivia (03:41)

3. Potential Marriage Proposals

• The hosts suspect Kennesaw Guy might propose, and joke about the chaos if both men tried to propose.
  • Quote: “Is there any chance you think that he's gonna pop the question to you this weekend?” — Bert (04:38)
  • Olivia replies: “I think there's a chance. I do.” (04:42)

4. Olivia’s Justifications & Confessions

• The hosts question Olivia about honesty and emotional involvement.
  • Olivia admits her mother doesn't know the full truth (she knows Olivia is seeing "someone," not two people).
  • Olivia acknowledges she says "I love you" to both men.
  • Quote: “She knows I’m seeing someone. She doesn’t know about either guy.” — Olivia (06:04)
  • Quote: “You tell them both you love them.”
    “Yes.” — (06:50–06:53)

5. Ethics and Listener Judgment

• Hosts and listeners debate the morality of Olivia’s behavior.
  • Commentator (Listener call-in):
    “I just wanted to tell this bimbo that she is a female chauvinist pig. And I hope they find her out.” — (06:28)
  • The show acknowledges this would be controversial if the genders were reversed.
  • Quote: “If this was a guy... you’d be furious, Jess.” — Bert (07:27)

6. Logistics, Laughter, and the Reality Check

• The hosts joke about what might happen if both men meet accidentally (e.g., both in the limo).
• Olivia confesses the whole juggling act is "more exciting than tiring," but admits it’s starting to catch up with her as the stakes get higher.
  • Quote: “So far it's been more exciting than tiring because I really enjoy the craftiness. But... now I’m getting a little bit worn out about how I’m going to swing next weekend.” — Olivia (10:24)

7. Advice, Sympathy, and Accountability

• The hosts debate helping her—but ultimately emphasize she must manage the consequences herself.
  • Quote: “You gotta figure this out yourself, but at least we want to know about it.” — Bert (07:41)

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Memorable Quotes & Moments (with Timestamps)

• “Until this Valentine’s Day thing came up...” — Olivia (02:25)
• Kennesaw Guy’s extravagant gesture:
  “...look, I’ve planned something really special for us on Saturday night. I ordered a limo.” — Olivia (03:38)
• Realization about potential proposal:
  “Oh my gosh. I might say yes.” — Olivia (04:51)
• On telling both men ‘I love you’:
  “You tell them both you love them.” “Yes.” — Male Host & Olivia (06:50–06:53)
• Listener’s blunt criticism:
  “I just wanted to tell this bimbo that she is a female chauvinist pig...” — Caller Heather (06:28)
• Host calling out the double standard:
  “If this was a guy... you’d be furious, Jess.” — Bert (07:27)
• Olivia’s candid self-reflection about the stress and excitement:
  “So far it's been more exciting than tiring because I really enjoy the craftiness. But... now I’m getting a little bit worn out about how I’m going to swing next weekend.” — Olivia (10:24)

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Key Segment Timestamps

• 01:02 – Olivia returns for an update
• 02:25 – Valentine's Day plans become problematic
• 03:38 – Kennesaw Guy's limo surprise
• 04:38–05:14 – Speculation about a possible proposal and its repercussions
• 06:28 – Listener calls in, criticizes Olivia
• 07:27 – Hosts debate the gender double standard
• 09:14 – Olivia confirms intimacy with both men
• 10:24 – Olivia starts feeling the strain
• 10:50 – Segment ends and transitions away from main content

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Tone & Style

• Conversational, humorous, and sometimes blunt—hosts mix sympathy, moral debate, and sarcasm.
• Listeners engage openly—some with support, many with sharp criticism.
• Olivia remains candid—owning her complicated choices and the thrill, but showing a hint of exhaustion as her situation becomes harder to control.

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Summary Takeaway

This episode highlights the real-world chaos of modern dating, especially when one stretches the truth too far. Olivia’s story—a real-life romantic juggling act—offers both comic relief and a cautionary tale, with the Bert Show acting as a chorus of moderators, judges, and therapists. By the end, Olivia's excitement seems tinged with anxiety, as Valentine's Day looms with both possibilities and potential fallout.

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Listeners are left eagerly awaiting the next update: Will Olivia’s double life unravel, or will she continue pulling off the ultimate romantic balancing act?

Transcript

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[SpinQuest Disclaimer Voice]

Hey, the Birch Show.

[Radio Host (Lead)]

All right, Olivia. Let's get back with Olivia here. A couple of weeks ago, she called us up, and she was making a very bold move. Moving. Went in with two different guys, two different apartments around Atlanta.

[Olivia]

You know, moving is always stressful, but neither one of them on Saturday seemed like they had an inkling of what might be going on. I spent the night with Kennesaw guy on Saturday night, and then Sunday, I went back to my apartment. Midtown guy came over.

[Radio Host (Lead)]

Were there two very special nights with two very special guys on different nights this weekend?

[Olivia]

Yes.

[Radio Host (Lead)]

Okay, so the key in this thing also is she's told both guys, look, don't expect me to fully commit to being here all the time because my mom is going through a very emotional divorce right now, so she's using that to get out of the house and sort of go from dude to dude. So that was two weeks ago, wasn't it?

[Radio Host (Male Commentator)]

You guys talked to her for the first time and ended the story two weeks ago when I was out of town. So it was like a week and a half.

[Radio Host (Lead)]

She's juggling both these dudes now for two weeks, and let's see if it's worth it here. Hey, Olivia. Good morning.

[Olivia]

Good morning.

[Radio Host (Lead)]

How are you today?

[Olivia]

I'm pretty good. And as far as living in two houses goes, it's been going really well.

[Radio Host (Female Commentator)]

Really?

[Olivia]

Yeah. Yeah.

[Radio Host (Female Commentator 2)]

You sound comfortable.

[Olivia]

Until. Until this Valentine's Day thing came up.

[Radio Host (Lead)]

Yeah, that was Jen's questions. Like, now, how are you gonna handle this?

[Radio Host (Female Commentator 2)]

Yeah. Who do you spend it with?

[Olivia]

Yeah. And, you know, obviously, I can't spend it with both of them. So I talked to Midtown Guy first and told him, you know, look, I have to work on Monday morning anyway, and Saturday night's a much better date night. So why don't we special on Saturday night, and then I can spend Valentine's Day with my mother, you know, and make sure she's okay on that romantic holiday. So he said, you know, that's great. We'll do that. And so then I talked to Kennesaw Guy and we made plans for Valentine's Day evening. But then Kennesaw Guy says, and I also told Kennesaw Guy that I was going to be at my mother's on Saturday night, that I was going to wake up with her on Valentine's Day morning, spend some time with her. And so then Kennesaw Guy has Valentine's Day evening. But then he also says, look, I've planned something really special for us on Saturday night. I ordered a limo.

[Radio Host (Female Commentator 2)]

Oh, yeah.

[Olivia]

And he can't. He can't afford a limo. So this is a. This is like a really big deal,

[Radio Host (Male Commentator)]

especially on Valentine's night. Don't limo companies do the same thing that flower companies do? The dozen roses that you bought last week that cost you 20 bucks are now 63 times.

[Radio Host (Male Commentator 2)]

Yeah.

[Radio Host (Male Commentator)]

The $150 limo rides now 450.

[Radio Host (Female Commentator 2)]

Right.

[Olivia]

So this is for Saturday night, the night that I was going to spend with Midtown Guy.

[Radio Host (Male Commentator 2)]

Right.

[Olivia]

And so. And I said, well, you know, I told my mother that I spent the night with her. And he said, you know, I'll get you home to your mother's house by 10 o', clock so you can still spend a little time with her before you go to bed.

[Radio Host (Male Commentator 2)]

So he wants to spend Saturday and Sunday with you?

[Olivia]

Yes.

[Radio Host (Male Commentator 2)]

Huh.

[Radio Host (Lead)]

He's in love with her. Why wouldn't he?

[Radio Host (Male Commentator 2)]

Well, I know I.

[Radio Host (Lead)]

They've moved in together. They're almost engaged.

[Radio Host (Male Commentator 2)]

I'm worried. That's exactly what I'm worried about.

[Olivia]

Oh, boy.

[Radio Host (Male Commentator 2)]

With Kennesaw Boy.

[Radio Host (Female Commentator 2)]

How long have you and Kennesaw Boy been dating?

[Olivia]

We've been dating for four months.

[Radio Host (Lead)]

Is there any chance you think that he's gonna pop the question to you this weekend?

[Olivia]

I think there's a chance. I do.

[Caller 1]

Oh, no, I mean that.

[Olivia]

Like the limo. Saturday night? Yeah.

[Radio Host (Male Commentator 2)]

What would you.

[Olivia]

Oh, my gosh. I might say yes.

[Radio Host (Female Commentator 2)]

And then you just ditch Midtown Guy?

[Olivia]

Well, I don't know if I ditch it.

[Radio Host (Lead)]

Oh, come on, Seriously.

[Caller 2]

If you were engaged to Kennesaw Guy, you would not.

[Radio Host (Lead)]

You would just keep.

[Olivia]

I would probably ditch Midtown Guy.

[Radio Host (Lead)]

Yes, probably.

[Olivia]

Yeah, probably.

[Radio Host (Lead)]

What if both of them proposed to you this weekend?

[Radio Host (Female Commentator 2)]

Oh, shut up.

[Caller 2]

Oh, boy.

[Radio Host (Female Commentator 2)]

That's like a story.

[Radio Host (Male Commentator)]

Maybe. You know what?

[Radio Host (Female Commentator 2)]

Maybe it doesn't really happen.

[Radio Host (Male Commentator)]

If Kennesaw guy does propose to you to save money, maybe you can both move in with Midtown guy.

[Radio Host (Male Commentator 2)]

Yeah, he's one with all the money, right?

[Radio Host (Lead)]

Good morning, Stephanie. You're on Q100. Hello. Hey, Stephanie.

[Olivia]

Hey.

[Radio Host (Lead)]

Hi.

[Radio Host (Female Commentator)]

I'm just curious. What does she do if one of these guys wants to end up going over to her mom's house at all?

[Radio Host (Lead)]

Yeah, what if. What if he's gonna propose this week and he calls your mom and, like, asks for your hand or something like that?

[Caller 2]

They both do.

[Radio Host (Male Commentator)]

Or they both do. The call waiting clicks over while she's on the phone with one of them. Hold on, I got another call.

[Olivia]

Click.

[Radio Host (Male Commentator 2)]

Does she know about any. Either one of them?

[Radio Host (Female Commentator 2)]

Yeah.

[Radio Host (Lead)]

Did you tell us that part of the whole thing?

[Olivia]

She knows I'm seeing someone. She doesn't know about either guy.

[Radio Host (Male Commentator 2)]

Okay.

[Caller 1]

Neat. Yeah.

[Radio Host (Lead)]

So you're not honest, really, with anybody

[Radio Host (Female Commentator 2)]

in your life except us.

[Radio Host (Male Commentator)]

Does anything more that matter than us?

[Radio Host (Female Commentator 2)]

I mean, really, where your therapy couch here is?

[Radio Host (Lead)]

Oh, no. She's not even asking for it. She's got it worked out. Hey, Heather.

[Radio Host (Female Commentator)]

Hello.

[SpinQuest Disclaimer Voice]

Hey.

[Radio Host (Female Commentator)]

I just wanted to tell this bimbo that she is a female chauvinist pig. That's exactly what she is. And I hope they find her. I hope they find out. And I hope one of them calls her mom's or asks her mom's number or whatever.

[Radio Host (Lead)]

Do you tell. I do. You say I love you to each one of these guys every day?

[Caller 1]

No, not every day when you're drunk.

[Radio Host (Male Commentator 2)]

But you've told them. You tell them both you love them.

[Olivia]

Yes.

[Radio Host (Male Commentator 2)]

Yeah.

[Radio Host (Lead)]

So at this point, what are you going to do this weekend then?

[Olivia]

Well, that's what I was hoping you would help me with.

[Radio Host (Lead)]

You're not getting a lot of help over here.

[Olivia]

Well, how can we help? I didn't think I needed any help with the move. You guys called me initially, but now that we're in this together.

[Radio Host (Lead)]

That's awesome.

[Olivia]

Now that we have her handle Valentine's

[Radio Host (Female Commentator 2)]

Day, I think you've got to. All right, if we're just setting aside whether this is right or wrong and actually help her try to figure it out, which I'm gonna do right now against my better judgment.

[Radio Host (Lead)]

This is so. First of all, let me. Let me. I'm throwing the protest flag on this. No. If this was a guy. Again, if this was a guy and it was the other way around, you'd be furious, Jess.

[Radio Host (Female Commentator 2)]

You're right. You're right.

[Radio Host (Male Commentator 2)]

Double standard. Yeah.

[Radio Host (Lead)]

I mean, you gotta figure this out yourself, but at least we want to know about it.

[Radio Host (Male Commentator 2)]

I kind of want you to go on this limo ride with Kennesaw boy.

[Olivia]

I don't. I mean, I don't think. I can't not go. That sounds so exciting to me.

[Radio Host (Lead)]

Well, and think about how this dude's showing up. Because Kennesaw guy is the guy that doesn't have a lot of cash. But here he is. He's getting a limo for you. He's got something really special planned. And Rich guy in Midtown. What has he got planned for the weekend? Nothing yet, right?

[Olivia]

Yeah. Probably just dinner on Saturday night.

[Radio Host (Male Commentator 2)]

If Kennesaw boy ends up proposing to you and you say yes, you've got to clean up your act, period. Because you're being so cruel to these men.

[Radio Host (Lead)]

Hey, Aaron. Good Morning. You're on Q100.

[Caller 1]

Hey, Bert. I was just saying that I think Olivia is really taking tire kicking to a new level. I mean, it's pretty typical for women to have a checklist. You know? They'll say, well, I want this, this, this, and this and a guy. But then they'll also have the guy they like. And I think she's just going back and forth, comparing them.

[Caller 2]

I mean, she shouldn't have moved in with him.

[Radio Host (Lead)]

Well, you got some decisions to make, because they're both going to come at you strong this weekend.

[Olivia]

Yeah.

[Radio Host (Male Commentator)]

The first decision you make is what time. Can you join us on Monday?

[Radio Host (Lead)]

Hey, Dwayne. Good morning. You're on Q100.

[Caller 1]

Good morning. I want to ask this girl, this lady, is she having sex with these guys?

[Radio Host (Lead)]

Are you intimate with both dudes?

[Olivia]

What do you think?

[Radio Host (Lead)]

Yeah.

[Olivia]

Yeah.

[Radio Host (Male Commentator 2)]

I mean, you're living with both of them.

[Caller 1]

Yeah.

[Caller 2]

Yeah. You already said you had two special nights on that weekend you moved in. So, of course,

[Radio Host (Lead)]

here's Good Morning. Q100.

[Caller 1]

Yeah, I just had a question. What if both guys are in the limo when they show up?

[Caller 2]

Oh, boy.

[SpinQuest Announcer]

Beautiful.

[Radio Host (Lead)]

They found out about each.

[Radio Host (Male Commentator)]

Guys aren't that smart.

[Radio Host (Lead)]

We just get angry and women fist through, you know, like a wall.

[Radio Host (Male Commentator)]

Women would do that and guys wouldn't spend the money. Like, if one guy said, hey, let's split a limit.

[Caller 2]

Well, maybe Midtown guy bought it because he's got all the money.

[Radio Host (Female Commentator 2)]

Okay, could be.

[Radio Host (Lead)]

All right, so as it stands right now, you're confused. You have no idea what the plan's gonna be for Valentine's Day.

[Olivia]

Correct.

[Radio Host (Lead)]

Well, at least check it out.

[Radio Host (Female Commentator 2)]

I feel too bad.

[Radio Host (Male Commentator 2)]

Predicament.

[Radio Host (Female Commentator)]

Yeah.

[Olivia]

Yeah. Well, I mean, what I think I'm gonna do is I'm gonna find some way to get in that limo, but he can't drop me off at my mother's house afterwards because that'll be really awkward.

[Radio Host (Lead)]

No, you're on your own on this.

[Olivia]

I haven't been there in a while.

[Radio Host (Lead)]

We don't even have a chance. I wonder, like, isn't this tiring for you, like, to try to keep up the stories in your own mind on who you're supposed to.

[Olivia]

So far it's been more exciting than tiring because I really enjoy the craftiness. But I'm now, just. Now I'm getting a little bit worn out about how I'm going to swing next weekend.

[Radio Host (Lead)]

You're so sort of like cold and mean about it though.

[Radio Host (Male Commentator)]

Like, I'd be careful with the use of the word swing, to be honest with you.

[Radio Host (Lead)]

All right, Olivia, we will talk to you next week. Okay?

[Olivia]

Okay.

[Caller 1]

All right. Bye bye.

[Olivia]

Bye bye.

[Radio Host (Lead)]

That kind of like coldness and just kind of like that. She's really sort of getting off by the whole reception of the whole thing.

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[Olivia]

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