Vault: Would You Wear A Used Engagement Ring?

Summary

---

Podcast Summary

The Bert Show (Pionaire Podcasting)

Episode: Vault: Would You Wear A Used Engagement Ring?

Date: January 12, 2026

---

Overview

In this lively and authentic episode, the cast of The Bert Show dives into a provocative conversation inspired by an episode of Desperate Housewives: If you’re getting engaged, would you accept a used engagement ring—especially one that belonged to your partner’s previous spouse? The conversation expands to whether a new ring should be bigger than the ex’s, the meaning behind engagement ring size, and societal competitiveness around weddings. With real listener calls and classic banter, the team explores both the romantic and the materialistic sides of engagement traditions.

---

Key Discussion Points & Insights

1. Desperate Housewives Proposal as Catalyst

• Jen recounts an episode where Teri Hatcher’s mom gets proposed to with a ring belonging to the proposer’s deceased wife, sparking debate.
• Quote:
  • [02:16] Michelle (reading show dialogue): “It's a three carat diamond. I mean, she... shouldn't care if it's... it's used. Sophie, would you do me the honor of marrying me?”
  • [02:29] Show narration: “Tomorrow we trade this in for a ring of my own. And I want a bigger diamond than Dolores got.”

2. Is a Used Engagement Ring Ever Okay?

• The cast agrees the gesture feels awkward—receiving a ring that once belonged to someone else feels secondhand, especially if the previous relationship ended poorly.
• Liza observes forgiveness due to age, but suspects younger couples would break up over it.
  • [02:49] Liza: “Well, the fact that he was using another woman's ring, engagement ring, to give to her, you know, was wrong... if they had been in their 20s, I think they would have broken up.”

3. Does the New Ring Need to Be Bigger?

• Central debate: If your partner has been married or engaged before, should your ring be bigger than their ex’s ring?
• Liza ties it to celebrity culture, comparing Jennifer Garner’s ring from Ben Affleck to JLo’s much larger one from him.
  • [03:19] Liza: “I do think that if you are the next one... it has to be bigger.”
• Jen wonders if women should ask for a bigger ring, or if men just instinctively “know.”
  • [04:32] Burt: “I think a guy, it should be understood. I think a guy would just know that. Like, wouldn't you want to do that as a guy?”

4. How Does One Find Out Ring Sizes and Make Expectations Known?

• The logistics: How do you even bring up your partner’s previous ring size?
• Liza says if the woman had a previous engagement, friends or family can be asked, but in general, the implication is: “make a woman feel special—do better than last time.”
  • [05:42] Liza: “If you are with this woman now and you’ve been with somebody else before, you make things bigger and better because you're making her feel special.”

5. Authentic Experiences and Listener Calls

• Caller Sydney shares her husband was previously married, and her ring is indeed bigger, without explicit discussion.
  • [06:12] Sydney: “I just got married and my husband had previously been married and my ring is bigger now.”
  • She justifies it through both feeling special and financial changes over time.
• Other listeners call in with differing perspectives:
  • One woman says, “All that matters is if he loves you or not.”
    • [06:45] Sydney: “I was just saying that I don’t understand why women... want a bigger ring. All that matters is if he loves you or not.”
  • The cast humorously challenges her, joking about what makes one a “real woman.”
    • [06:52] Burt: “Oh, come on. Who are you? You do not have real breasts.”

6. Materialism vs. Sentimentality: The Core Tension

• While some argue for love over luxury, the cast leans into the common (if unstated) competitive edge of relationships.
• Liza calls out the competitiveness among women about making sure they “win” over their partners’ exes.
  • [07:14] Liza: “It's about competition... Women are always competitive with their man's ex-girlfriends and want to make sure that she's prettier... or that the ring is bigger.”

7. Celebrity Comparison and Personalization

• Callers and hosts differentiate ring styles to fit personalities, but the consensus is “cost matters.”
• When comparing Jennifer Garner (modest) and JLo (flashy):
  • [08:37] Sydney: “JLo is really flashy and showy. Jennifer Garner is much more refined... an engagement ring really needs to reflect the woman.”
  • Burt undercuts this, saying at the end of the day, the public will always see the dollar value:
    • [09:05] Burt: “But the bottom line is, Jennifer Lopez still trumped her ring by $2 million, and everyone knows that.”

8. Humor and Hyperbole: Keeping It Light

• Ton and Jen joke about Tic Tac boxes filled with diamonds—no matter what the gesture, someone will always find fault if it doesn’t count as “special.”
  • [10:50] Burt: “You should just give her an old Tic Tac box filled with loose stones... Look, here’s $3 million worth of diamonds.”

9. Lingering Impact and Shaping Expectations

• Caller Kelly (divorced and in a new relationship) never cared about previous ring size—until this conversation, which now plants the seed: “Now, for the rest of my life, I'm gonna be like, it's gotta be bigger.”
  • [11:36] Sydney (Kelly): “I never once thought about it. Now I think about getting engaged again... if he ever proposes, The Bert Show is going to be in my head the day that he does it.”

---

Notable Quotes & Memorable Moments (with Timestamps)

• [02:29] Show narration: “Tomorrow we trade this in for a ring of my own. And I want a bigger diamond than Dolores got. But she was no longer naive.”
• [03:19] Liza: “But I do think that if you are the next one, it's… yeah, I think it has to be bigger.”
• [04:32] Burt: “I think a guy, it should be understood. I think a guy would just know that.”
• [05:42] Liza: “You make things bigger and better because you're making her feel special.”
• [06:45] Sydney (caller): “I don’t understand why women want a bigger ring. All that matters is if he loves you or not.”
• [06:52] Burt (joking): “Oh, come on. Who are you? You do not have real breasts.”
• [09:05] Burt: “Jennifer Lopez still trumped her ring by $2 million, and everyone knows that.”
• [10:50] Burt (joking): “You should just give her an old Tic Tac box filled with loose stones. Go. Look, here's $3 million worth of diamonds.”
• [11:36] Kelly (caller): “Now for the rest of my life, I’m gonna be like, it’s gotta be bigger.”

---

Important Timestamps

• 01:17-02:07: Desperate Housewives episode recap and used ring debate introduction
• 02:29-03:19: Cast dives into the “should it be bigger?” discussion
• 04:08-05:08: How ring sizes and expectations get communicated
• 06:11-06:59: Caller Sydney’s real-life example and cast humor
• 07:14-08:15: Competition and materialism
• 08:31-09:38: “Ring should suit the woman,” but cost still reigns
• 10:50: Jokes about alternative engagement gifts
• 11:16-12:01: Final caller reflects on how the conversation recalibrates her expectations

---

Tone

• Energetic, unfiltered, playful, and honest
• A mix of pop culture analysis, personal anecdotes, and listener perspectives
• Lots of ribbing, self-deprecation, and witty banter

---

Summary

Would you wear a used engagement ring? The Bert Show’s cast and listeners mostly agree: probably not, and if your partner’s been engaged before, the new ring better be at least bigger or somehow “better” to mark your unique place in their life. While one or two voices remind us that “love is what matters,” the prevailing current is that of social competition—sparkle, size, and sentiment all battling for top spot on the ring finger. As always, the Bert Show keeps it real (and hilarious), making even the most superficial debates an oddly honest mirror on our culture.

---

Transcript

[Blue Apron / Advertisement Voice]

When you think about meal kit companies, what do you see? Probably long, complicated recipes and subscriptions you can't escape. But with the new Blue Apron, we're doing meal delivery differently. No subscription needed, faster, easier meals, and the same dedication to quality we've always had. Shop 100/[e-mail], get 50% off your first two orders with code apron50. Terms and conditions apply. Visit blueapron.com terms for more. BetterHelp Online Therapy bought this 30 second ad to remind you right now, wherever you are, to unclench your jaw, relax your shoulders, take a deep breath in and out. Feels better, right? That's 15 seconds of self care. Imagine what you could do with more. Visit betterhelp.com randompodcast for 10% off your first month of therapy. No pressure, just help. But for now, just relax.

[Burt]

The Burch show.

[Jen]

Desperate Housewives last night. Jen, I can't believe you missed Desperate House. That's like your only appointment television.

[Ton]

I know, but it's TiVo.

[Burt]

TiVo.

[Ton]

You can't tell me too much because I'm gonna watch it. Ton.

[Jen]

All right, I'll just give you what happens in the first couple of minutes of the show. Because I keyed in on one thing during the show here. There are actually a couple of pretty decent storylines, but Teri Hatcher's mom has been living with Teri Hatcher for a while now, right?

[Ton]

Driving her crazy. Just kind of like that last virtual listener we were talking about.

[Jen]

Pretty much same thing. Driving her absolutely nuts. Well, in the beginning of the show, the mother's ex boyfriend shows up to the house.

[Ton]

Okay.

[Liza]

Okay.

[Jen]

And he proposes to Teri Hatcher's mom. Teri Hatcher's all relieved, gonna get her mom out of the house and all. But here's a little bit how the proposal goes right here. Okay?

[Liza]

Oh.

[Blue Apron / Advertisement Voice]

Did this ring belong to Dolores? You gave her your dead wife's ring? It's a.

[Michelle]

It's a three carat diamond. I mean, she. You know, she shouldn't care if it's. It's used. Sophie, would you do me the honor of. Of marrying me?

[Blue Apron / Advertisement Voice]

Sophie Brehmer was still a hopeless romantic. On one condition. Tomorrow we trade this in for a ring of my own. And I want a bigger diamond than Dolores got. But she was no longer naive.

[Jen]

All right, There are a couple of things that are so wrong about that, obviously.

[Liza]

Well, the fact that he was using another woman's ring, engagement ring, to give to her, you know, was wrong. Uh, you know, but I think, you know, and I thought last night that based on their age is the reason she forgave him and just gave. You know what? Just trade that in and get me a bigger diamond. Where if they had been in their 20s, I think they would have broken up.

[Jen]

Yeah, that's the thing I want to focus in on. That's the thing I want to focus in on. Right, right there. It's the size of the ring. Does it have to be necessarily bigger than the X? You know what I'm saying?

[Liza]

Well, yeah. Yes, because. Yes, because, you know, this made me think of something that I read like last week. And I know that, you know, Jen and entertainment Buzz keep talking about, you know, Jennifer Garner and Ben Affleck. And the thing that I read about the fact that the diamond band, he's given her a diamond band and it's worth $500,000. Okay, now, if you remember back when he proposed to JLo, that was a $2.5 million, 6 carat ring. Now Jennifer Garner, you know, does not have as nice of a ring on her finger as JLO did. But Mark Anthony, his engagement ring to JLO was actually a seven karat ring. So he made sure that his engagement ring was bigger than Ben Affleck. So Jennifer Garner is kind of getting the shaft and all that. But I do think that if you are the next one, it's. Yeah, I think it has to be bigger.

[Jen]

Yeah, that's what I want to ask women. Like if you, if you're the woman getting the ring now and you know, he was either engaged or married previously, would you make the demand that the ring that you get from your man is bigger than, than the previous ring?

[Ton]

Like in a conversation before you get engaged, you tell him, do you, it better be bigger? Is that what you're saying?

[Jen]

I don't know. Is that how it works? I mean, is it really that important?

[Burt]

I think the guy, I, it should be understood. I think a guy would just know that. Like, wouldn't you want to do that as a guy?

[Jen]

But how would you find that out? Like, you'd go up to Jessica and you'd say, so how big was that ring?

[Burt]

That I don't think it's, I don't think women are secretive about that. Like, you know, like, I almost think it would come out with, yeah, and then he tried to marry. I should have known it was over when he gave me a measly three carat ring. Then you're like, oh, damn it, gotta.

[Michelle]

Upgrade on that one.

[Burt]

Shoot.

[Jen]

So somehow, some way, you have to make it known what the size of the ring was. So this dance has to go on and then a guy has to absolutely must get a bigger ring.

[Liza]

Well, the thing is also though, like in. In last night's example, he had already been with somebody else. So it should be understood if the guy had proposed to someone else before he's proposed to the woman he's talking to now. He knew how much that old ring, you know, how big it was. So he. I mean, a guy has no excuse, if he's done the proposing the whole time on to get something bigger, you know. But if she's been engaged before, there's a way to find out from friends, from mother, you know, like it doesn't have to be her.

[Jen]

And then how do you. I'm still a little confused on how you let him know.

[Liza]

Okay, you know what, Bert, again, make a woman feel special. And if you are with this woman now and you've been with somebody else before, you make things bigger and better because you're making her feel special.

[Ton]

Yeah, but think about it. In your own relationship, it'll make more sense if you had proposed to Chandra and given her a big old, you know, two carat ring. And then when you and Stacy decided to get engaged, think about not upgrading it from that.

[Jen]

Yeah, and you'd be paying for it.

[Ton]

The rest of your life.

[Jen]

Hey, Jamie.

[Sydney]

Hello.

[Jen]

Good morning.

[Sydney]

Hey, what's up? Yeah, I just. Just got married and my husband had previously been married and my ring is bigger now.

[Liza]

Was that understood or did you have to say something to him?

[Sydney]

Oh, I didn't have to say anything. You know, a few years later, you're also in different financial positions as well, so it should be larger.

[Ton]

If that's how you want to justify it, that's right. That's fine with us.

[Jen]

Good morning, Liza. You're on all the hits Q100.

[Sydney]

It's Liza, but I was just saying that I don't understand why women and want a bigger ring. All that matters is if he loves you or not.

[Burt]

Oh, come on. Who are you? You do not have real breasts.

[Sydney]

Oh, I swear. Well, actually, no, I don't have any breasts at all. My breasts are really small.

[Burt]

That's what I mean. You're not a real woman.

[Liza]

Oh, come on.

[Sydney]

A bigger diamond doesn't make me not a woman.

[Jen]

That makes you more of a woman to me.

[Sydney]

I just don't like. I don't think it's right to base your love on a material dimension.

[Burt]

It's not right, but that's the way women operate.

[Liza]

Not Me, I will never have an engagement ring, but I get it. Okay? And the thing is, it's about compet. It's always about competition. If, you know, you talk about superficial this, superficial that, with the engagement ring, but women are always competitive with their man's ex girlfriends and want to make sure that she's prettier, that she, you know, like, is it just about competition? If a guy got an engagement ring, it'd be the same thing.

[Sydney]

Well, I can. I can understand the competition area, but I just. I mean, I would do it on a different level. It doesn't have to be a bigger diamond. Just, you know, makes it the proposal better.

[Liza]

Yeah.

[Jen]

So long as you got the man in the end, why would it matter what size the ring is?

[Sydney]

So that's the way I feel.

[Ton]

But see. Oh, she hung up. I wanted to ask her if she was married or engaged. Because that's fine in theory, right? Once you apply it to reality in your own relationship, things change. That's why I brought up the ex girlfriend, the Chandra thing, because it brings it all in perspective. Like, yes, you're right. Stacy's not materialistic. And she, you know, would be absolutely in love with you anyway and married to you anyway. But had that ex girlfriend gotten a bigger ring?

[Jen]

Forget it.

[Ton]

All of that theory, that nice little, you know, hippie earth mother thing goes out the window.

[Jen]

You will never hear the words come out of my wife that my. Out of my mouth. That my wife is not materialistic. I promise you that. And she would agree if she was in here.

[Ton]

Really?

[Jen]

Yes. Hey, Sydney, you're on all the hits. Q100.

[Sydney]

Good morning, Burt Shell. How is everybody?

[Jen]

Good. How are you?

[Sydney]

Good. You guys are just awesome.

[Jen]

Thank you.

[Burt]

We know.

[Sydney]

I was listening. And I wanted to make a comment that comparing Jennifer Garner and JLo. First of all, they're totally different people.

[Liza]

Doesn't matter.

[Blue Apron / Advertisement Voice]

J.

[Sydney]

Lo is really flashy and showy. Jennifer Garner is much more refined. And that made me think about the fact that, you know, an engagement ring really needs to reflect the woman. And so if you've got a woman who is refined and tasteful and she would prefer something probably more delicate and.

[Burt]

More attractive, that's fine on paper. That's like, you know what I mean? It's like, what's the freaking Bowl Conference thing that you guys talk about every year? The bcs, where it all is supposed to come together on paper, but then somehow, like, you know, Gonzaga, whose basketball team ends up winning the football, you know, championship because of the way they put their math Together, that's the same thing. You go, oh, she's a different type of woman. She wouldn't want to be that showy. But the bottom line is that Jennifer Lopez still trumped her ring by $2 million, and everyone knows that. So in the back of her mind.

[Jen]

You think she's holding onto that?

[Burt]

I think it's in the back of her mind that JLO was good enough for a $2 million ring, a house and stuff, Savannah, all this other stuff. And Jay Garn has got herself. You know, I guarantee, like, Percentage wise, it's 20%. If you had bought Chandra a $10,000 ring and then Stacy a $2,000 ring.

[Liza]

I guarantee, before this is over with, because Jennifer Garner and Ben Affleck been trying to keep their relationship subtle, that this love band, this diamond, half million dollar love band is going to be accentuated with a fine rock before this is over with.

[Ton]

I think so, too.

[Jen]

More expensive than J. Lo's.

[Liza]

Absolutely.

[Ton]

I think it can be stated like, I don't think because the one that he got for JLO was like that pink, humongous one stone rock that was like, really, you know, like the last color said, like flashier or whatever. Like just more, you know, just more showy. And maybe Jennifer Garner's personality is to have something a little bit more subdued. As long as he spends more money. I think the style can be different. It could be a fat band and it could be flat. Like, maybe there wouldn't even be a solitaire on there. And maybe it was just, you know, you know, maybe a different designer that's more expensive. I think it could be a different style, more subdued style, but still has got to cost more.

[Burt]

You should just give her an old Tic Tac box filled with loose stones. Go. Look, here's $3 million worth of diamonds.

[Michelle]

Even that doesn't do it.

[Burt]

You're more important to me than JLo. So here you go.

[Jen]

Hey, Michelle, you're on all the hits, Q100 or not.

[Burt]

You can just shake out what you want.

[Liza]

But even then, that would. Oh, you didn't think plan ahead enough to put those actually in a ring for me? You're making me do it. It's all on me. What are you talking about? You don't love me. You love JLo. See, it'd be a problem.

[Jen]

Good morning, Kelly. You'll be the last call. Go ahead.

[Sydney]

Okay. I am divorced and currently in a relationship with a man who's also divorced. And my ex husband had been previously married. And when he gave me a ring. I never once thought about it. And now I think about getting engaged again. And I think to myself, oh, my God, if he ever proposes, the Burt show is going to be in my head the day that he does it.

[Liza]

Did you?

[Jen]

That's where we want to be.

[Liza]

What did you do with your old engagement ring? I'm curious.

[Sydney]

Um, it's still sitting in a box in the drawer.

[Jen]

So now how are you gonna tell him what size that ring was so he knows?

[Sydney]

To tell you the truth, I had never even thought about it. Even when my ex husband, who had been previously married, proposed, I never thought about his ex wife's ring ever. And now all of a sudden, now for the rest of my life, I'm gonna be like, it's gotta be bigger.

[Jen]

Turning healthy women unhealthy.

[Liza]

That's right.

[Burt]

You're welcome.

[Jen]

That's what we're all about.

[Burt]

Glad to help.

[Jen]

Thank us later. Bye, Kelly.

[Burt]

Bye. The Birch Show.

[Michelle]

In a world where January is supposed to be boring, one staple of the holidays refuses to end the great deals. At Verizon, the joy just keeps on coming. Right now, you can save on four new phones and four lines. Critics agree it's the deal that keeps on giving. Come into Verizon and save on four new phones and four lines on unlimited. Welcome. Additional terms applied. See verizon.com for details. The playoffs start this weekend, and now you can trade on football legally nationwide on Kalshee. Right now, Pittsburgh is trading at 38% to beat Houston. That means a $100 trade pays out 264 with a win on Cowshe you're trading against peers in a live market, meaning there's no house. And as the odds change, you can buy in or out of your position all game long. And for a limited, download the Kalshi app and use code iheart to get $20. When you trade 100k a l s h I kalshi trade on anything.

[Jen]

Say hello to Samantha.

[Blue Apron / Advertisement Voice]

Hi there.

[Jen]

Samantha built a SaaS platform that helps small businesses manage their workflow. But she needed a smarter way to reach decision makers.

[Blue Apron / Advertisement Voice]

That's where Acast came in. They helped me produce a professional audio ad which played to business owners and ops leads using their audience attributes targeting tools. Suddenly, my platform was showing up in the ears of the exact people I needed to reach.

[Jen]

Now, that's streamlined marketing. Samantha, what's your tip for scaling smart?

[Blue Apron / Advertisement Voice]

Solve a real problem and make sure the right people hear about it.

[Jen]

Promote your business with podcast ads on Acast. Get [e-mail] advertisement.