Vault: She's Convinced He'll Propose Over the Holidays

Summary

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The Bert Show – Episode Summary

Episode: Vault: She’s Convinced He’ll Propose Over the Holidays
Air Date: June 1, 2026

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Overview

In this lively and candid episode, the Bert Show crew dives into a classic dilemma: Joanna is convinced her boyfriend, Jason, might propose over their upcoming holiday cruise—and she can’t help but obsess over every possible sign. The segment explores the mind games, mounting expectations, and (often comedic) anxiety that can accompany waiting for a marriage proposal. The hosts share personal stories, expose the anticipatory "engagement spiral," and debate the merits of snooping versus letting the surprise naturally unfold. A key theme: balancing the desire for romantic surprise with the often unavoidable urge to figure it all out in advance.

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Key Discussion Points & Insights

Joanna’s "Engagement Imminence" Spiral

• Duration & Anticipation:
  • Joanna and Jason have been together nearly two years. She feels an engagement could happen “at any moment” and admits she’s been stuck in this mindset for about six months.
  • “I’m really excited about this one. Well, Jason and I are at that time where we could possibly be getting engaged at any moment.” – Joanna (01:20)
• The Endless Waiting Game:
  • The hosts commiserate about how women often set themselves up for disappointment by attaching proposal expectations to trips, events, and even breakfasts.
  • “...you keep playing this mind game with you, and you’re disappointed and disappointed and disappointed.” – Bert (01:58)

The Accidental Email & Raised Suspicions

• Joanna recounts Jason accidentally forwarding her an email that mentioned he might propose in January, which heightened her anticipation—and skepticism that he may now deliberately change plans to throw her off.
• Jason now keeps mentioning a January ski trip, making Joanna overthink whether he’s misdirecting her away from the cruise.
• “I think he’s trying to throw me off and making me think it’s still gonna happen in January, but it might actually happen over on the cruise.” – Joanna (03:17)

The "Snooping" Instinct

• The conversation turns to whether Joanna can (or should) resist the urge to snoop through their cruise cabin for a hidden ring.
  • The crew jokes about Joanna potentially ruining her own surprise but laughs about the near-universal curiosity/vigilance that accompanies big life moments.
  • “What made you think I didn’t already think of this?” – Joanna (04:51)
• Hosts debate the merits of surprise versus certainty, with Bert pleading:
  • “If it’s gonna happen on the cruise, then why do you need to snoop to find a ring that you’re gonna get in three or four days anyway and ruin the surprise?” – Bert (05:03)
• Joanna, self-aware:
  • “She can’t help herself. It’s like a craving. She can’t stop.” – Bert, about Joanna (05:14)

Games, Dresses, and Out-Smarting Each Other

• Joanna meticulously plans what to wear for a potential proposal and even wants to borrow a friend’s dress for the occasion.
• Hosts poke fun, warning she might be caught off guard:
  • “He’ll probably throw you off, and you’ll be in your, like, ratty pajamas. Or it’ll be like the night before... That’s when he’ll propose.” – Joanna (06:57)
• The conversation shifts to the idea that men should be “allowed” their big proposal surprise, and Joanna’s efforts to anticipate the moment may undermine that.
  • “This is the one thing that the dude gets to really get his hands, like, dirty when it comes to the engagement. So let him have it.” – Bert (07:05-07:18)
• Tracy finds humor in the “battle of wits”:
  • “I think this is funny and fun... Jason’s gonna propose, so he knows that, she knows that. So now it’s just a wily game of who can out trick who...” – Tracy (05:48)

Listener Stories & Cautions

• Callers chime in sharing similar experiences and offering advice:
  • One listener shares how knowing about her engagement in advance took away the magic:
    • “...when you’re on that trip, every single moment... ruins it. Because you’re like, oh, I see it in his pocket, and I know it’s gonna happen.” – Caller (07:43)

Parental Perspective: Joanna’s Mom Joins

• Madhura, Joanna’s mom, admits she too has probed Jason for details but insists she’d keep the secret if she found out.
  • “Women like to, you know, to find out things in advance so we can be prepared.” – Madhura (11:04)
• Advises Joanna to relax and enjoy her trip—if it’s meant to happen, it will.
  • “She needs to, you know, relax and enjoy her trip, you know, and whatever happens, it’s gonna happen. But just don’t, you know, don’t go crazy about it.” – Madhura (12:16)
• Madhura notes Jason might change his original plan to surprise Joanna, demonstrating just how deep the expectations cat-and-mouse goes.

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Memorable Quotes & Moments

• On sabotaging the surprise:
  • “Why would you even want to ruin that?” – Bert (04:49)
  • “She’s a snooper.” – Multiple hosts (04:53)
• On expectations:
  • “You were totally setting up expectations that will never be met. And it’s going to ruin the surprise, and it’s going to ruin the moment because it’s never going to be exactly how you’re thinking. Just let him have his moment and his glory...” – Caller Tracy (08:58)
• On letting go:
  • “Go have fun, enjoy your trip. And probably he’s gonna wait... because he knows that you expect it and he doesn’t want [you to know].” – Madhura (13:38)

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Timestamps for Key Segments

• 01:00 – 02:27: Joanna details her suspicions and recounts the “proposal cycle.”
• 03:02 – 03:40: The accidental email; debating if Jason’s actually throwing her off.
• 04:29 – 05:17: Debate over snooping and the risks of ruining the surprise.
• 06:06 – 06:40: Wardrobe dilemmas—what to wear if it happens.
• 07:43 – 08:07: Listener relates her own engagement disappointment.
• 10:14 – 13:21: Joanna’s mom joins; discusses secrecy, advice for Joanna, and family tendencies to snoop.

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Tone & Atmosphere

True to The Bert Show’s style, the episode is light-hearted, irreverent, and authentic. The team balances playful teasing, real relationship insight, and communal storytelling, making listeners laugh while reflecting on very real personal anxieties and hopes about milestone moments.

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Bottom Line

If you haven’t listened:
The episode is a fun, relatable deep dive into the rush and torment of waiting for "the moment"—with sharp wit, great stories, and a healthy dose of empathetic teasing. Whether you’re Team “Let It Happen” or Team “Snoop To Know,” you’ll find yourself reflected (and maybe gently roasted) by Bert, Joanna, and the crew.

Transcript

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[Host Bert]

The Birch Show. We just talked to a whole bunch of Birchall listeners. Have some pretty dramatic storylines going on over Christmas and New Year's that we'll check back with on when we get back on the first or whatever. Second. And Joanna may have her own dramatic storyline going on as well, but she always feels like the same storyline's going

[Joanna]

on for the last six months.

I'm really excited about this one. Well, Jason and I are at that time where we could possibly be getting engaged at any moment.

[Madhura (Joanna's Mom)]

Oh, no.

[Joanna]

Because here we go again. We could be getting engaged. Means he better hurry up and propose because we have been dating for a long time.

[Host Jeff]

Do you even listen to Bert and I when we speak?

[Joanna]

No. Yeah. Rarely.

[Madhura (Joanna's Mom)]

What.

[Joanna]

How long have you guys been together?

It'll be two years in March. So. Well, if you remember. Well, I mean, don't you think.

[Host Tracy]

Well, I think anywhere from if you're dating somebody, if you're a guy and you're. You've passed the one year mark, just know that she thinks you're proposing at any moment. Further you go, the more it intensifies.

[Host Bert]

It's such. It's an awful position for a woman to put herself in because Jenna's told us this before. It's like you get to this certain point and you just assume, and it is probably here, that the engagement is imminent. It's gonna happen. But every minute that goes by or every day that you see him, you think, okay, maybe it's gonna be today. And then you think, oh, we got this really cool thing Friday. But he's gonna do it Friday. And it doesn't happen on Friday. Then you're like, Oh, I bet it's gonna be when we're on the cruise and then you get back from the cruise and. And you keep playing this mind game with you, and you're disappointed and disappointed and disappointed.

[Joanna]

Yeah, I ruined, like, two years worth of vacations with that.

[Host Jeff]

Like, every time, like, you'd say, let's get up early and have breakfast, you're like, I know what you mean by breakfast.

[Host Bert]

Right.

[Host Tracy]

Always looking in your, you know, like in your champagne glass or whatever. Is there a ring at the bottom of this glass?

[Joanna]

Well, I'm headed down that path, too, because we.

[Host Jeff]

What do you mean, headed down? You're at the end of that path, and you're making a campsite in the middle of it.

[Joanna]

And we are going on a cruise for New Year's. And he sent me an email a couple, like, a month ago accidentally revealing that he was going to pop the question in January. I don't know if you remember me telling you about that.

[Host Bert]

He was sending this to somebody else that.

[Joanna]

You saw it, right? And it was accidentally forwarded to me. I saw it. All I saw was, hey, I'm going to do it in January. And when I told him, he said he was going to change the date. He's like, you know what? You should have told him why? Right, I shouldn't have. But now he said he's going to change the date. Well, he keeps talking about this ski trip in January and how excited he is in January and how amazing it's gonna be. I think he's trying to throw me off and making me think it's still gonna happen in January, but it might actually happen over on the cruise.

When do you guys leave for the cruise?

We leave the 26th, the day after Christmas.

Okay.

Yes, but now.

[Host Bert]

I'm sorry. Go ahead.

[Joanna]

No, it's okay.

[Host Bert]

My bad.

[Host Tracy]

And you come back when? In January?

[Joanna]

Yes, we come back January 4th. It is still January 4th, 1201. Not the trip that I think it might happen. Are you.

[Host Bert]

Aren't you gonna, like, continuously, like, each and every day? With each and every event, you're gonna think there's another he's gonna propose, and you're gonna be disappointed on this cruise when it doesn't happen.

[Joanna]

Well, and then another key to this is that one of the nights we're having a really fancy dinner and he's bringing his uniform to wear.

[Host Jeff]

Well, that's. You do that on a cruise. You always take your uniform basically wear.

[Joanna]

You wear, like, a tie, not your army blue dress.

[Host Jeff]

Yeah, well, there's a formal. I Did. I mean.

[Joanna]

Yeah, yeah.

[Host Bert]

That was a Cub Scout uniform.

[Host Jeff]

No, it wasn't. I wear. I have a military uniform that I wear in the airport, so they get free upgrades to first class.

[Joanna]

Well, my question for you, though, is, in a cruise, like, one of their selling points is you only unpack once. So there's going to be a chance for you to snoop through that cabin. When he is, like, at the pool or he's at the bar, he's like, honey, I'm going to go play blackjack. We're in international waters now, or whatever, and you're going to be like, I. I'm gonna go back to the cabin and, quote, take a nap.

[Host Bert]

Why would you even want to ruin that?

[Joanna]

What made you think I didn't already think of this?

She's already thought of it. Cause she's a snooper.

Yeah.

And she works in your office every day, buddy, so you be careful because she has snooped through there through and through.

[Host Tracy]

There's nothing.

[Joanna]

I picked through it. There's nothing in there but this engagement.

[Host Bert]

Like, if it's gonna happen on the cruise, then why do you need to snoop to find a ring that eventually you're gonna get in three or four days anyway and ruin the surprise?

[Joanna]

She can't help herself. It's not a consciousness.

[Host Bert]

Women are nutty.

[Joanna]

It's like a craving. She can't stop.

[Madhura (Joanna's Mom)]

Stop it.

[Host Jeff]

What if the other side of that coin is on day one of the cruise?

[Host Bert]

He jumps off and swims for sure.

[Host Jeff]

You got to get some on the first day of the cruise. What if she tears that cabin up and down when he goes out for a walk or whatever and doesn't find it? Then the rest of the cruise is ruined.

[Host Bert]

Ruined. Why don't you just let it happen when it happens?

[Joanna]

I will still have a great time regardless, because I'm going to be on a cruise in the middle of the ocean having a great time. But if there is a ring involved, it'll be extra awesome.

[Host Tracy]

See, I think this is fun. No, you know what? But I think this is funny and fun, as opposed to maybe some other couples we talked to, because Jason's gonna propose, so he knows that, she knows that. So now it's just a wily game of who can out trick who, you know what I mean? And that's kind of fun.

[Host Bert]

She has this thing so played out. Like she's got questions in her mind on what dresses to wear.

[Joanna]

Yes. So I have a dress that my friend wore one night, and I saw her come home in this dress and it was gorgeous and looked great on her. And we're the same size that. So I was like, can I please borrow that dress for the cruise? Cause I'm gonna wear it the night of. You know, we go to the formal dinner. If he proposes on that night and I'm wearing her dress, am I allowed to keep her dress?

[Host Jeff]

No.

[Joanna]

No. Why? I say no.

[Host Tracy]

Why would no. But as the owner of the dress, I might let her keep it or

[Joanna]

give it to you. She offers for.

[Host Tracy]

She has to offer.

[Joanna]

Yeah, but you can't ask for it.

What if I bought her a replacement dress? No, same dress. But, you know, if you're gonna do

that, then go ahead and buy a different dress that you bought.

[Host Bert]

You guys realize there is no engagement yet, right? We're talking potentially about addressing case because,

[Host Tracy]

you know, just let women deal with women things.

[Joanna]

Here's the thing.

He'll probably throw you off, and you'll be in your, like, ratty pajamas. Or it'll be like the night before you guys go out hammered, you end up sleeping in his T shirt. That's when he'll propose.

[Host Bert]

I hope. I hope. Because you're making it impossible for him. Jeff has said this for years, and it's so true, and that this is the one thing that the dude gets to really get his hands, like, dirty when it comes to the engagement.

[Host Tracy]

I do agree with him.

[Joanna]

He's still.

[Host Bert]

So let him have it.

[Host Tracy]

He is.

[Joanna]

He can have it, but it has to be on the formal dinner.

[Host Jeff]

You know what?

[Joanna]

My creme brulee.

[Host Tracy]

It's a challenge for him again. I think it's a challenge for him to outsmart you, and I think that he would take that challenge home.

[Host Jeff]

The challenge should be finding a new girlfriend.

[Host Bert]

The challenge should be, here is Sue.

[Host Jeff]

I mean, you're pretty and all Joanna, but you're a lot of work.

[Host Bert]

Hey, sue, you're on the voice disguiser.

[Madhura (Joanna's Mom)]

Go ahead.

[Caller]

Hey. I just want to let you know, like, I knew when I was getting engaged, because I sat on the ring and we went on a trip, and when you're on that trip, every single moment on that trip, you're like, okay, it's gonna happen now. It's gonna happen now. And it ruined it. I mean, it ruined it. You tried to do something really special, go back to the car and take it down to where we went and do all this. And it just ruined it. Because you're like, oh, I see it in his pocket, and I know it's gonna happen.

[Host Bert]

This is the only thing that he gets to Own for years and years and years that you guys, you'll ask, you know, how did he propose to you? This is the one thing he gets to control, and you're taking the fun out of it for him.

[Joanna]

I mean, I think it's already ruined because I saw the email because so I already know it's coming soon.

[Host Jeff]

I hope he walks in here right now and does it. Total surprise.

[Host Bert]

Like, I think if he really wants to shock her, he's got to break up on this cruise.

[Host Tracy]

Yes. The first day. So they're stuck on the boat together,

[Host Bert]

get engaged the next day.

[SpinQuest Announcer]

Oh, my God. That's.

[Host Jeff]

That's the plot of a movie.

[Host Tracy]

What? Breaking up the first day.

[Host Jeff]

Right. He goes on the cruise to get engaged, and they're in the cabin together, and she gets in a fight with him, and they break up on the first day, and then they have to stay in the same cabin. He's trying to win her back so he could propose.

[Host Bert]

Hey, Tracy, you're on Q100.

[Caller Tracy]

Hey, guys.

[Joanna]

Hi.

[Caller Tracy]

Listen to Bert and Jeff.

[Joanna]

Oh, she's serious.

[Caller Tracy]

So much pressure as women on men with this whole engagement. And the last caller is right. You were totally setting up expectations that will never be met. And it's going to ruin the surprise, and it's going to ruin the moment because it's never going to be exactly how you're thinking. It's in your brain. Just let him have his moment and his glory, and it just. Yeah, because you're going to ruin it for yourself.

[Host Bert]

It's already ruined. It's already ruined for him. It's not ruined. It is ruined.

[Host Tracy]

No, it's not ruined.

[Host Jeff]

You know what you need to keep in mind during this whole. Everything that you're doing right now, Joanna is Tiger woods wife. Okay.

[Host Tracy]

Because do Tiger woods wife.

[Host Jeff]

No, Keep her in mind.

[Caller Tracy]

Oh.

[Madhura (Joanna's Mom)]

Oh.

[Host Jeff]

Cause the point I'm making is I think Joanna moved through life with a certain amount of confidence because Joanna's hot, Right. So she moves around. And confident.

[Host Bert]

I'm not confirming or denying that.

[Host Jeff]

And confident and, you know, funny. And would be considered a good catch on the surface. So would Tiger woods wife. But something she did made him stray.

[Joanna]

Yeah, right.

[Host Bert]

Joanna's madre.

[Joanna]

Hi.

[Madhura (Joanna's Mom)]

Hey. How is everybody doing in there?

[Joanna]

Really good.

[Host Bert]

Madre. We are very concerned with Joanna, and we are very concerned with her robbing Jason of this engagement.

[Madhura (Joanna's Mom)]

I know. I am, too. And, well, I know it's gonna happen, and I swear to God he haven't said anything to me. And I try. I try to see if he can give me some information. Hold on. I'm in school right now, so that's Jason.

[Host Tracy]

Go.

[Madhura (Joanna's Mom)]

All right. I have tried to talk to him and see if he can give me something. Not that I want to tell Joanna, because I don't want to spoil. You know her. You know her. Surprise.

[Host Bert]

She's a woman.

[Host Tracy]

She's gotta find out.

[Host Jeff]

But now we know where Joanna gets it from. Cause, like, you're grilling the poor guy.

[Host Bert]

You're sort of snooping.

[Madhura (Joanna's Mom)]

Women like to, you know, to find out things in advance so we can be prepared.

[Host Bert]

Now, hold on one second here, madhura. Cause if you found out that he was gonna propose, you couldn't keep that secret from your daughter.

[Madhura (Joanna's Mom)]

Oh, yes, I can.

[Host Bert]

You think?

[Joanna]

So he's kept secrets.

[Host Bert]

Oh, yes, I can. Okay.

[Host Tracy]

Women can keep secrets.

[Madhura (Joanna's Mom)]

Yes. You know, I know it's gonna happen, and she know it's gonna happen, but he's gonna do it when she least expect it.

[Host Tracy]

Right.

[Host Jeff]

In 2014.

[Host Tracy]

But see, now, the two men on this show are guys that really didn't jump into marriage very quickly. If I recall that there was three

[Host Jeff]

years as soon as Jessica.

[Host Tracy]

But wasn't there an ultimatum with you? And then as soon as Jessica, we gave you crap on the air.

[Host Jeff]

As soon as Jessica told me she was gonna move back to Arizona, I decided that we should move back.

[Host Tracy]

So I'm just saying. I just wanted. I just want to say that the guys didn't necessari necessarily come up with the idea totally on their own.

[Host Jeff]

Do you know why, Melissa?

[Madhura (Joanna's Mom)]

Oh, you're right.

[Host Jeff]

We were waiting for the perfect time to surprise.

[Host Tracy]

If that was the. You would never do it.

[Host Jeff]

We were working through the anticipation. It's gonna happen.

[Host Tracy]

I just wanted to. I just wanted to put that on the table.

[Host Bert]

So. Madre. So are you calling Joanna to tell her to relax about it?

[Madhura (Joanna's Mom)]

Yeah, she needs to, you know, relax and enjoy her trip, you know, and whatever happened, it's gonna, you know, it's gonna happen. But just don't, don't, you know, don't go crazy about it.

[Host Jeff]

Let me. I have a question for Joanna's mom.

[Host Tracy]

She's like, I'm trying to find out

[Host Jeff]

if, knowing how you are, you know, do the. You have the little snooper gene in the Rodriguez family now.

[Madhura (Joanna's Mom)]

She's taken from the fordomos.

[Host Jeff]

If Jason came and spoke to Mr. Rodriguez, Joanna's dad, and asked for his permission to marry Joanna, what would he even tell you?

[Madhura (Joanna's Mom)]

My husband? Yes, he will.

[Host Jeff]

That's a bad move on his part

[Host Bert]

because then you're going to turn around, you're going to tell.

[Madhura (Joanna's Mom)]

So who can't keep you get when you be married for such a long time that we are. We cannot keep it from each other because we feel uncomfortable about that. You know, I agree. And you do have to tell your husband, you know, your wife what's going on. But you had to make him promise not to say anything to anybody else.

[Host Bert]

Like, I mean, I think again, you have to look at the Tiger woods situation. Look how he had complete full disclosure with his wife. They've been married for years now. And after like the 13, he totally told her. I mean, they had full disclosure also.

[Madhura (Joanna's Mom)]

Yes.

[Host Bert]

So there's the mom.

[Joanna]

So mom advices to chill out, chill

[Madhura (Joanna's Mom)]

out, go have fun, enjoy your trip. And probably he's gonna wait maybe, you know, until spring to ask because he knows that you expect it and he don't want. He told me he is. He's gonna go to plan B. But he never say what plan B was.

[Joanna]

It's always a plan B. Yeah, he

[Madhura (Joanna's Mom)]

got the plan A, it failed and now he's going to plan B.

[Host Jeff]

Plan B. I'm not getting married till Melissa can legally get married.

[Madhura (Joanna's Mom)]

Oh, my God. That would be a good excuse for.

[Host Bert]

Hey, the Burt Show.

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