Vault: Did Her Boyfriend Surprise Her With A Proposal Over The Holidays?

Summary

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The Bert Show – "Vault: Did Her Boyfriend Surprise Her With A Proposal Over The Holidays?"

January 26, 2026 | Pionaire Podcasting

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Episode Overview

This episode centers on listener Sharon’s ongoing saga of hoping for a marriage proposal from her boyfriend after five years together. The cast checks in with Sharon post-holidays to find out if her boyfriend finally popped the question. The group shares empathy, humor, and candid advice as Sharon details her anticipation, letdowns, and evolving feelings. The conversation broadens into a relatable discussion about relationship timelines, expectations, and the fine art of balancing patience with self-respect.

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Key Discussion Points & Insights

Setting the Scene: Sharon’s Hopeful Wait

• Sharon has called into the show multiple times with updates, each time hoping her boyfriend would propose. This episode continues the thread as the holidays (Christmas and New Year's) have just passed.
  • Burt: "It’s pretty much the same story every time we talk to Sharon. ... That makes you think, okay, this is gonna be it." (00:04)
• Sharon spots a small box under her boyfriend’s Christmas tree, convinced it’s an engagement ring.
  • Sharon: "Underneath his Christmas tree is a small box and it's a little ring box." (00:22)
  • The cast jokes about the possibility that it's jewelry, but not an engagement ring.
  • Steve: “What about earrings?”
  • Stacy: “Shut up.” (00:30)

Unwrapping the Letdown

• Sharon recounts the Christmas gift-exchange – the box contained earrings, but for his mom, not her.
  • Sharon: "It was earrings from his mom. ... It wasn't even jewelry for me." (02:12, 02:19)
  • Sharon describes the awkward moment at his parents’ house expecting a proposal, only for the box to go to his mother.
  • Sharon: "He picked up this box and he hands it to his mom. I thought I was gonna die." (03:08)
• Presents from her boyfriend are met with indifference – Sharon only had eyes for the (mom’s) earring box.
  • Jeff: “She didn’t even try them on.” (03:51)
  • Sharon: “I don’t know, some crappy sweater, I don't know. Not really.” (04:34)

Reflecting on Relationship Timelines

• After feeling repeatedly let down, Sharon sets a mental deadline of Valentine’s Day to get serious about her future.
  • Sharon: "If it doesn't happen by then, because I have to get serious." (05:18)
• Jen relates, having gone through the same anticipation with her own husband:
  • Jen: "Once you've been dating for that long ... you're ready for them to propose. You're ready to take that next step in your life, and they're just not on the same page." (01:07)
• The group discusses the emotional difficulty of repeatedly psyching oneself up for an engagement that doesn’t happen.
  • Burt: “That’s the thing that Jen was saying was so dangerous about this whole scenario, is that you can’t reboot your attitude.” (05:43)
    • Jen: “It’s hard and it’s disappointing, and there’s nothing you can do.” (06:13)

Listeners Chime In: Advice and Tough Love

• Stacy, a caller, gives blunt advice about not “giving the milk away for free”:
  • Stacy: "Why buy the cow when you can get the milk for free? ... Baby girl, you've got to seriously move on." (06:37)
• Burt and the team explore how best to express one’s feelings without pressuring a partner:
  • Burt: “Stacy gave me an ultimatum ... So the ultimatum worked in my case.” (08:11)
  • Jeff: “It was when we were going to a friend's wedding, and she just pointed out the number of weddings of people that we have been to ... since we started dating together.” (08:58)

The Gender Divide and Internal Deadlines

• Steve notes men and women often perceive marriage differently, with men seeing it as the end of freedom and women viewing it as the beginning of a dream realized.
  • Steve: “Weddings and guys and proposals is not something they're looking forward to. ... Guys are a little slower to getting it done.” (09:43)
• Burt strongly advocates for personal boundaries and secret deadlines:
  • Burt: "Set a date in your own head. And if he makes it, great ... and if not, then it's time to move on." (10:09)
• Other listeners call in to echo the advice, sharing how setting an internal (or external) deadline shifted their mindset – and sometimes their relationships.
  • Stacy (caller): "I gave him a deadline and not really told him that this is your ultimatum. ... I got so disgusted ... I was like, I don't care if we get married. I'm getting myself ready to be single again." (10:49)
• Stacy also offers an amusing “stench” theory: when you truly stop caring, the desperation “stink” goes away, and that shift can actually prompt change in the partner.
  • Stacy: "As my husband likes to say, the stench will be off of you. ... Then he'll realize what he has and you'll be married." (12:14)
  • Burt/Jeff: "Stench of desperation. ... Not even a smell or a whiff. A stench like the rotting flesh of a roadkill raccoon." (12:51, 12:56)

Sharon’s Final Word

• Sharon sets a concrete timeline for herself:
  • Sharon: “I give them till Valentine’s Day, and then I’m … I’m taking my toothbrush out of the house.” (13:13)
• The group wishes her luck and promises to check in after Valentine’s Day.
  • Burt: "That's a start, right? All right, we'll talk to you soon." (13:19)

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Notable Quotes & Memorable Moments

• "You can't reboot your attitude."
  — Burt, reflecting on the difficulty of shutting off hope once it starts (05:43)
• "Why buy the cow when you can get the milk for free?"
  — Stacy (caller), giving tough love to Sharon (06:37)
• "The stench will be off of you."
  — Stacy (caller), on how true emotional detachment changes relationship dynamics (12:14)
• "Set a date in your own head. And if he makes it, great... and if not, then it’s time to move on."
  — Burt, on personal boundaries and self-respect (10:09)
• "I give them till Valentine’s Day, and then I’m taking my toothbrush out of the house."
  — Sharon, drawing her own line in the sand (13:13)

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Key Timestamps

• 00:22 — Sharon suspects boyfriend's small box is a ring
• 02:12 — Discovery: the box was earrings for his mom
• 03:08–03:37 — Sharon describes painfully watching the gift go to his mom
• 04:45 — The repeated letdowns across holidays (Christmas, New Year’s)
• 05:18 — Sharon sets a Valentine's Day deadline
• 06:37 — Stacy's "Why buy the cow..." advice
• 08:11 — Stories of how hosts handled or received ultimatums/deadlines
• 10:09 — Burt advocates secret personal deadline strategy
• 12:14 — Stacy's “stench will be off you” metaphor
• 13:13 — Sharon: “Valentine’s Day or I’m moving out” final declaration

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Episode Tone & Takeaways

The episode is a classic Bert Show blend of humor, empathy, and straight talk. Listeners will find camaraderie and laughter in the cast and callers’ stories, but also receive hard-earned wisdom on the importance of knowing your worth and setting boundaries in long-term relationships. Sharon’s experience is both an entertaining saga and a springboard for a broader, honest conversation about love, timing, and self-respect.

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Transcript

[Jeff]

The Burt Show.

[Burt]

All right, we got a wrap up proposal Sharon here. See what happened to her over the weekend. It's pretty much the same story every time we talk to Sharon. We could have played any one of these conversations that we had with her. Hey, Sharon, what is lined up? Like, what is any different this week than there has been for the last couple of weeks? That makes you think, okay, this is gonna be it.

[Sharon]

He has a Christmas tree in his place, and underneath his Christmas tree is a small box and it's a little ring box.

[Steve]

What about earrings?

[Stacy]

Shut up.

[Sharon]

I'm not talking to you.

[Burt]

Well, I can't do this.

[Sharon]

I'm in denial.

[Jeff]

Sharon.

[Jen]

The only thing is, why would he put it underneath the tree already? If he was trying to surprise you with a ring, he would have kept it hidden, don't you think?

[Burt]

You're not even thinking like a person with any kind of common sense because you're so eager to get engaged.

[Sharon]

Okay, I don't care. Yes, it's true. But I think it's gonna be on Christmas. That's what I think.

[Burt]

Okay, so as the story goes, if this is the first time you're hearing from Sharon, she's called us four different times. Yeah.

[Jen]

And they have been dating for five years. And I totally understand where she is because once you've been dating for that long, which is the same situation I was in with my husband, you're ready for them to propose. You're ready to take that next step in your life, and they're just not on the same page. So it gets to that time where every special weekend, or he can even sneeze funny, and you think he's about to propose.

[Burt]

The anticipation is there with every move. Right.

[Jen]

You're just anxious for it to happen. And so you just. You get yourself all psyched up in your mind that it's gonna happen. So we understand where she's coming from. We just didn't want her to be disappointed around every corner.

[Burt]

So there that little box was under the Christmas tree, shaped like it could be a ring in there. This is gonna happen.

[Jeff]

Could be a ring, could be anything.

[Burt]

Here's Sharon. Hey, Sharon.

[Sharon]

Hello.

[Jen]

Hi.

[Burt]

You're back on the voice disguiser.

[Sharon]

Hey. How you guys doing?

[Burt]

Good. How are you doing?

[Sharon]

I'm doing okay. Did you have a good Christmas?

[Jen]

We did.

[Sharon]

No.

[Steve]

What was in that box?

[Sharon]

Do you know what was in that box?

[Steve]

You tell me.

[Sharon]

It was earrings from his mom.

[Jeff]

Let me list.

[Jen]

For his mom.

[Sharon]

Totally.

[Burt]

For his mom.

[Sharon]

For his mom. It wasn't even jewelry for me.

[Steve]

So when you saw him in the jeweler that day, he was getting his mom's Christmas gift.

[Sharon]

Oh, I never. Yeah, maybe he was getting his mom a Christmas gift. Yeah, probably.

[Burt]

So now was it the kind of Christmas where mom was there also? So you guys were opening up your present then? She was opening a present than maybe he was. And that last box was there and then he handed it to his mom or was it just gone from the Christmas tree?

[Sharon]

No, we went over to his folks house for Christmas and so he gathered up, you know, the presents under the tree and he gathered up that box. And so I thought, oh, maybe he's going to ask me at his folks house in front of his parents.

[Stacy]

Oh, God.

[Sharon]

And yeah, so now we've had two holidays then. So we went there, you know, and it was sort of like he was like playing Santa with the hat on or whatever and everybody was sitting around and so he's handing out the presents and he had the box and he's like handing everything out. And then he picked up this box and he hands it to his mom. I thought I was gonna die.

[Burt]

That was the only box that you even had your eyes on. Everything else.

[Sharon]

I could have cared. He gives me all these big bo clothes, like, clothes and this, you know.

[Steve]

They were at least the right size, right? Cause that's always dangerous.

[Sharon]

Whatever, it didn't matter.

[Jeff]

She didn't even try them on. She's like. I remember like my parents told me this story when I was like five or six years old of me at my grandma's house going through the gifts and like, I would open a box, it would be socks right over my shoulder, like, didn't even care. Open another one. Underwear right over my shoulder. Open another one. Scarf. Didn't care. Hand knit by my grandmother or whatever. Didn't care. Throw it toy. Game on.

[Burt]

Right?

[Jeff]

She's doing the same thing with that earring box. Totally.

[Sharon]

That's what I felt like. And I'm just eyeing this box his mom's got, hoping that maybe he's gonna go, oh, no, this is for you. I felt like an idiot.

[Burt]

Could you even name like three presents that he gave you on Christmas?

[Sharon]

I don't know, some crappy sweater, I don't know. Not really.

[Jen]

And then we've gone through two holidays now. You guys had New Year's Eve to get through too?

[Sharon]

Yeah, yeah, I know. We went through New Year's Eve, Christmas.

[Steve]

I was evil.

[Sharon]

I didn't care. After Christmas, I was sort of like, I didn't think he was gonna. I Was not gonna set myself up to think about New Year's Eve. And we had a kind of a quiet New Year's Eve. And I think I. I kind of feel like I'm gonna give him till Valentine's Day, and then we've been together for five years, so I'm gonna have to start thinking about it if. If it doesn't happen by then, because I have to get serious.

[Jen]

This is a change in tune from you.

[Burt]

Yeah, totally.

[Steve]

Yeah.

[Sharon]

Yeah. But I, you know, maybe. Because I just sort of got my hopes up, and I saw him at the jewelry store and I thought, oh, you know, here comes that. But I have to kind of think about it. Five years. That's a long time.

[Burt]

That's the thing that Jen was saying was so dangerous about this whole scenario, is that you can't reboot your attitude. It's like you're excited about it, and it's not like you can just turn it off and go, you know what? I'm just not excited about getting engaged anymore. Because you know in your heart of hearts that you are. You can't lie to yourself.

[Sharon]

How long did it take your husband after you thought he was gonna ask you?

[Jen]

Too long.

[Sharon]

What's that? Too long? It's like a day too long. Yeah.

[Burt]

Yeah.

[Jen]

It just.

[Burt]

Yeah.

[Jen]

It's hard and it's disappointing, and there's.

[Burt]

Nothing you can do.

[Jeff]

Hey, Steve, I keep visualizing all these coffee mugs and bumper stickers and T shirts with. You can't reboot your attitude on it. Like, you are three hours into the new show. And here they come. Buddha bird is.

[Steve]

Bumper sticker Buddha.

[Burt]

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

[Stacy]

Good morning. How are you guys doing?

[Burt]

Good, thank you.

[Stacy]

I just have to say, and I feel so bad for this girl. I mean, baby girl, please. There's a saying that goes, you know, why buy the cow when you can get the milk for free? Another mother sticker getting them free for five years.

[Sharon]

You did not say that.

[Stacy]

I'm. Baby girl. I'm sorry. He's been getting it for free for five years. So basically, if he can still get it for free for another year, he's going to ride this thing out. Baby girl, you've got to seriously move on.

[Sharon]

Sharon, you say ride this thing out? Really?

[Stacy]

He's been riding it out for five.

[Burt]

Years already, so there's no sense of immediacy for him. I'm assuming, and I think you've told us this before, that maybe you put him in the pressure cooker a little Bit like he knows how you feel about it.

[Sharon]

Well, yeah, we've talked about it, but I don't feel like I put it in the pressure cooker. I don't feel like I've been all up in his business about it. But he knows that I want to get married. He knows that I want to have kids.

[Jen]

Does he know that you're disappointed? After the holidays.

[Sharon]

I might have been a little cranky, but not. I don't think I was obvious, but maybe I was. I don't know.

[Steve]

Now, I know that memory can sometimes be short, but both guys in the room were a little, you know, slow to the punch when it came to proposing to their wives. So I'm asking them, what's the best way to let you know for sure you're the one I want to marry. I want to get married, and. But then leave it be, like, well, how do. How should she communicate with her boyfriend, finally, and then let it go.

[Burt]

My story is just a little unique, and I've told it before, that Stacy gave me an ultimatum. I got a job in Dallas, and we were living in Washington, and she said, this is where my whole life is. This is it. My parents are here, my friends are here. I went to school here. So if you want me to pack up and go to Dallas with you, I'm sorry, you're going to need to give me a commitment. And she gave me an ultimatum. And I waited to the very last second, and I said, hey, will you come to Dallas with me? Will you marry me? So the ultimatum worked in my case. What about you, Jeff?

[Jeff]

I think with Jessica, it was never really an ultimatum, but I think the thing that weighed at, like, she said one thing to me when we were going to a friend's wedding that I think made me realize, you know, that how not important it was to her, but how.

[Steve]

You'Re on a deadline.

[Jeff]

Not really a deadline, but how foolish it just was that we weren't engaged yet, and it was when we were going to a friend's wedding, and she just pointed out the number of weddings of people that we have been to or that we were going to, like, hey, this is the fourth wedding that we've been to of people who have met, gotten engaged, and gotten married since we started dating together.

[Sharon]

Right.

[Jeff]

You know what I mean? Like, their entire relationship, you know, went in the course of ours. And I was like, all right, so.

[Steve]

It'S honestly a guy training loud and clear. It's obviously a guy trust.

[Sharon]

Maybe you boys will just drag your feet until we say Something, because I'm about done. I'm about, like, I'm gonna be a single girl. What did she say? Giving away the milk for free?

[Steve]

Well, that's such a millipede thing to say. But I think that you. This is the biggest, I think, miscommunication between men and women, because you gotta remember, guys, weddings and guys and proposals is not something they're looking forward to. It's almost like they're taught this is the end of their freedom, where women are kind of groomed to dream about the day in which they'll get married. So I do think it seems consistent that guys are a little slower to getting it done.

[Burt]

But, you know, inevitably, though, and I've said this before, that I really do think that it's a smart idea to have a deadline day in your head. And I have pointed to too many friends of mine, women specifically, that waited and waited and waited. Five, six, seven, eight years. You know, they started dating dude when they were, what, 22 years old, and now they're 30 years old, and he dumps her, and now she has to start all over again, and she's just looked at the last eight years, you know, So I. You know, if it was my daughter, I'd say set a date in your own head. And if he makes it great, don't pressure him. Don't tell him about the date if he makes it great. And if not, then it's time to move on.

[Steve]

And you remember you said that to.

[Jen]

Tracy when she was hoping for Scott to propose, too?

[Burt]

Yeah. Morning, Q100.

[Stacy]

Hey, Bert, I agree with you totally. I was at a point where I thought about it day in, day out, and it was making me sick. Every time he opened his mouth, I was like, oh, he's going to ask now. He's going to ask now. But I got so disgusted that I was just like, you know what? Forget this. I gave him a deadline and not really told him that this is your ultimatum. But I kind of said, you know, if anybody's together this long, it's ridiculous if they're not married already. So I thought I was kind of planting a seed and that would kind of rush them along. And I got so disgusted that it was at a point where I was like, I don't care if we get married. I'm getting myself ready to be single again. So it's good that she's turned this leaf and she's not really as desperate for it as she was, because New Year's could have been just horrible for her, but it Was just like another day. And they enjoyed it. Well, when I got to a point where I didn't care anymore, that's when he finally was like, hey, honey, they're having a bridal show this weekend. Do you want to go? And I was like, for what? To torture myself? Not interested.

[Burt]

Did you say that you told him what that deadline day was or you just had it in your own head?

[Stacy]

Oh, no, I told him. Well, we had friends that had been together for like 10 years, seven years, and they were still just dating. And I was like, you know, if anybody's together longer than three years, that's just too long. You need to break up already.

[Burt]

Yeah. The only difference here with me is that I don't think you ever tell him what your deadline day is.

[Stacy]

I just said, well, yeah, because it was way long after three years, when we got engaged, it was like four and a half years.

[Burt]

Yeah, you're always moving that line in the sand.

[Stacy]

Yeah. Uh huh.

[Sharon]

Uh huh.

[Burt]

It didn't happen this time, but I'll give him the Valentine's Day.

[Stacy]

It didn't happen exactly, because you don't really want to break up, but you just. You want to move into that next phase with that person that you love and adore. So hang in there. But if you get to a point where you're enough is enough, seriously, be at that point. Don't just, like, you know, make up stuff to get him to the altar. Decide within yourself that this is enough for me. And at that point, as my husband likes to say, the stench will be off of you. Because they said that men can smell a desperate woman miles and miles away. So that stink will come off of you, and then he'll realize what he has and you'll be married.

[Burt]

That goes both ways, too. Like, when you're a single guy, women can smell your desperation.

[Jeff]

Stench of desperation.

[Burt]

That is so true.

[Jeff]

It's not even a smell or a whiff. A stench like the rotting flesh of a roadkill raccoon.

[Burt]

All right, Sharon, good luck with everything. I guess we'll, you know, check back with you in a couple of weeks or so. I don't know.

[Steve]

She said Valentine's Day.

[Sharon]

I give them till Valentine's Day, and then I'm. I'm taking my toothbrush out of the house.

[Burt]

That's a start, right? All right, we'll talk to you soon.

[Sharon]

Okay, bye.

[Burt]

Bye.

[Sharon]

Happy New Year, guys.

[Jen]

Happy New Year.

[Jeff]

The bird show.