Vault PT 1: Bad Ultimatum

Summary

---

The Bert Show – Vault PT 1: Bad Ultimatum

Date: November 5, 2025
Podcast by: Pionaire Podcasting
Main Cast: Bert, Kristen, Abby, Cassie, Tommy, and guests
Episode Theme: The pitfalls and peculiarities of romantic ultimatums—real listener calls, personal stories, and a candid, often comedic debate on whether (and how) giving your partner an ultimatum ever works in relationships.

---

Episode Overview

In this episode, The Bert Show team dives into the complicated (and sometimes hilarious) world of relationship ultimatums, focusing on real-life stories and the fine line between motivation and manipulation. Host Bert and the cast recount personal experiences and open up the phone lines for listeners to share their own ultimatum tales—some of which are shocking both for their boldness and their outcomes. The hosts discuss not only when and how ultimatums take place, but what they reveal about partners, self-worth, and the expectations we bring into modern relationships.

---

Key Discussion Points & Insights

1. Bert’s Personal Ultimatum Story

[01:44 – 02:17]

• Bert shares how his now-wife Stacy issued him an ultimatum:

  “We are not going anywhere until I get a ring on my fingers. So if I wanted to bring her down to Dallas, she gave me the ultimatum. I bought hook, line, and sinker.” (Host, 02:17)

• The cast reflects on how some men need a strong push, but not all respond well:

  “I think some guys do. Other guys are really turned off by something like that.” (Host, 02:48)

2. Listener Call: The Three-Month Ultimatum

[02:08 – 06:36]

• A female caller shares her own story: after only three months of dating, she gave her boyfriend a clear ultimatum—propose by Valentine’s Day or it’s over:

  “Pretty girl, ring on my finger or don't call me anymore.” (Caller, 03:53)

• The hosts react with disbelief at the short timeline and the candor with which the caller describes “dating down”:

  “Hold on. You're telling me you're dating down? So if you're dating down, this guy should be easier to commit.” (Host, 03:57)

• The caller admits she’s made subtle “improvements” to her boyfriend’s appearance, further surprising the hosts:

  “You know, it'd be better if you got a little haircut or maybe comb that hair over. You know, I've switched his soap so that his face doesn't break out so often.” (Caller, 04:41)

• She confirms her feelings for him:

  “Yeah, I am [in love].” (Caller, 04:58)

• The hosts point out the double standard in relationships regarding “changing” partners:

  “It's no different than any other woman changing a man… She's just saying it out loud and we're getting offended.” (Host & Co-host, 05:01-05:05)

• The caller reveals she delivered her ultimatum over a special dinner, with wine:

  “[I] sat him down … and I want you to ask me to marry you or just don't call me anymore.” (Caller, 05:19)

• The boyfriend’s reaction: he said he’d discuss it with her on Valentine’s Day.
• She’s adamant: no ring, the relationship ends.

3. Call-In: Another Ultimatum That Worked

[06:46 – 07:29]

• A new caller describes having successfully issued a Valentine’s ultimatum to her now-husband:

  “I told him that he needed to propose to me by May 1st or he's gonna have to wait five years for me to get out of school … he actually did it on April 28th and completely surprised me. So it actually worked.” (Caller, 06:50)

• Bert notes that ultimatums can spur deep reflection:

  “It just made me really think, what is my life gonna be like without this woman in it? And that thought scared the hell out of me.” (Host, 07:17)

4. The Team’s Reflection: Is This Ever a Good Idea?

[07:17 – 08:36]

• Commentary on the “right” and “wrong” ways of giving an ultimatum.
• The cast questions the health of a relationship beginning with such intense pressure after only three months.
• Another revelation: the original caller has given ultimatums before—with previous boyfriends of varying attractiveness, showing she has a “pattern.”

“Have you ever given other [guys] ultimatums, Lena?” (Co-host 2, 07:57)

“Yeah, I did it once before.” (Caller, 07:59)

5. The Cliffhanger

[08:24 – 08:36]

• The show arranges to follow up with the first caller after Valentine’s Day to see if her boyfriend proposes or if she follows through on her threat to break up.
• “Now, that's the first part of that. Wait till you hear the second part. I'll play it for you next on the Best of the Bert Show.” (Host, 08:36)

---

Notable Quotes & Memorable Moments

• On the legitimacy of ultimatums:

  “Sometimes it works. Sometimes it doesn't. But there's definitely a right way to give a guy an ultimatum. And there's a wrong way.”
  (Host, 01:44)

• Caller’s self-assessment:

  “Well, he's, you know, he's a nice guy, but he's not a good looking guy. So it's not like he's gonna do any better for me.”
  (Caller, 03:44)

• Host’s incredulity:

  “After three months, you're pushing them right out the door.”
  (Host, 05:53)

• On romance vs. pressure:

  “Valentine's Day is probably the most romantic manufactured holiday created by Hallmark.”
  (Co-host 2, 02:51)

---

Timestamps for Important Segments

• [01:44] – Start of core topic: Bert’s ultimatum story
• [02:08] – Caller introduces her three-month ultimatum scenario
• [03:35] – Exploring the reasoning and how long caller has dated
• [05:19] – Detailed recount of how caller delivered the ultimatum
• [06:46] – Second caller shares her Valentine’s Day ultimatum-success story
• [07:17] – Bert reflects on the power of loss in making relationship decisions
• [08:24] – Preparation for follow-up with ultimatum caller

---

Tone and Delivery

In classic Bert Show style, the episode is lively and unscripted, mixing playful banter and humor with candid moments. The hosts challenge both guests and each other with tough questions, but keep the mood light even as they explore the more awkward or controversial sides of relationship dynamics.

---

Summary

This episode of The Bert Show confronts the risky game of relationship ultimatums head-on. Listeners hear real stories—both successful and questionable—while the cast offers their own experiences and strong opinions on the “right” and “wrong” ways to motivate commitment. With eyebrow-raising anecdotes (including a blunt “three months or bust” demand), the team highlights common pitfalls, double standards, and the emotional calculus behind the ultimatum. The cliffhanger sets up a follow-up episode: will the Valentine’s Day demand get results, or will it end in heartbreak?

---

Transcript

[Host]

The holidays are coming and I've got a Boost Mobile gift just for you. Aww.

[Co-host]

For me? Anna?

[Host]

Yes, Anna, you deserve a gift. The Boost Mobile unlimited plan is just $10 a month for the first two months, then $25 a month forever with unlimited data, talk and text.

[Co-host]

It's a gift.

[Caller]

Thanks, Anna. Anytime, Anna.

[Host]

The holidays are here and the best gift is for you. Offer [e-mail] after your first two months, you'll pay $25 a month unless you go online or call to cancel. Requires autopay.

[Advertiser/Voiceover]

So the other day I was in this group chat. Of course the topic turned to weight loss medications because it kind of seems like everybody's on one. One friend is already on one. Another is researching every option on Tick Tock and someone else was like, I don't even know where to start. It feels like everybody is talking about it right now, but nobody really knows if it's right for them. That's why hers can be a great option for you because they take all the confusion out of it. You connect with a real medical provider who helps you figure out what's actually best for your body and your goals without the guesswork. If it's prescribed, you'll get medication as a part of a doctor develop weight loss program with ongoing check ins, dosage adjustments and 24. 7 online support. They've got affordable options from oral medication kits to GLP1 injectables starting at 69amonth. So if you've been trying to figure out what works for you, it might be time to check out hers. Whether you want to lose weight, grow thicker, fuller hair, or find relief for anxiety, hers has you covered. Visit for hers.comb to get a personalized, affordable plan that gets you. That's f o r h e r s.comb for hers.comb weight loss by hers is not available everywhere. Compounded drug products are not approved or evaluated for safety, effectiveness or quality by the fda. Prescription required. See website for full details, important safety information and restrictions. Actual price depends on product and plan purchased.

[Host]

The Birch Show I've told you guys before that Stacy gave me an ultimatum to get married and I bought it hook, line and sinker. And in a lot of cases it works. Sometimes it doesn't. But there's definitely a right way to give a guy an ultimatum. And there's a wrong way. The perfect example of a wrong way to give an ultimatum on the Best of the Burke show on Atlanta's new Q100.

[Caller]

I'm calling because a couple of Days ago, you were talking on the air about women who give their boyfriend or their boyfriend an ultimatum.

[Host]

Yeah. Actually, this very thing happened with me and my wife when we were living in Washington, D.C. i got a job offer in Dallas, and I told her all of that. I was all excited. Yay, we're going to Dallas. We are going to Dallas. And she said, we are not going anywhere until I get a ring on my fingers. So if I wanted to bring her down to Dallas, she gave me the ultimatum. I bought hook, line, and sinker.

[Co-host 2]

Well, then, I mean, with Stacy was a little. Because then she went out and bought the ring.

[Host]

She said, you are in love with me and you are marrying me. Boy.

[Caller]

Well, I think men need that.

[Host]

I think some guys do. Other guys are really turned off by something like that.

[Co-host 2]

Bert was talking about the Valentine's Day ultimatum because, you know, Valentine's Day is probably the most romantic manufactured holiday created by Hallmark.

[Host]

Well, statistics show you that when it comes to ultimatums, when a woman thinks of one either in her mind or actually gives a date, 48% that give ultimatums do it on New Year's, but 35% have Valentine's Day as their ultimatum day. Like, you better get that ring on my finger this day, or we are done if it's set or not.

[Caller]

I just gave my boyfriend an ultimatum.

[Host]

You did?

[Caller]

Yes, I did. For this Valentine's Day.

[Host]

Now, is this a. This is a given one. So this is not one like a date in your mind, you have said to him, look, if Valentine's Day is your time.

[Co-host 2]

Mm.

[Host]

Okay.

[Co-host]

Yeah. Because my thing is with ultimatums, I think it also depends on how long you've been together. So how long have you and your boyfriend been together?

[Caller]

Three months.

[Co-host]

Oh, and you've already given him an ultimatum?

[Caller]

Well, he's, you know, he's a nice guy, but he's not a good looking guy. So it's not like he's gonna do any better for me.

[Co-host]

Now, what was the ultimatum you gave him?

[Caller]

Pretty girl, ring on my finger or don't call me anymore.

[Host]

Hold on. You're telling me you're dating down? So if you're dating down, this guy should be easier to commit.

[Co-host]

He should be grateful to you or something.

[Host]

How did.

[Co-host 2]

How did you present the ultimatum to him, and how did he take it?

[Caller]

I just told him, you know, it's been going really well. We get along, we like each other's families, things are good, and we have a nice chemistry between the two of us.

[Co-host]

And you've met families at three Months.

[Caller]

Yeah.

[Host]

Of course, sometimes things move fast. Of course. Everybody's done that. Yeah. Sorry.

[Caller]

Well, do you have to get your. You know, I want to see what they think of him.

[Host]

Now, do you tell him that you don't think he's good looking?

[Caller]

Not. Not that bluntly.

[Host]

I think he knows now.

[Co-host]

Oh, but you. What kind of hints do you give.

[Caller]

Him to let him know, you know, it'd be better if you got a little haircut or maybe comb that hair over. You know, I've switched his soap so that his face doesn't break out so often.

[Co-host 2]

Are you in love?

[Caller]

Are you in love with him?

[Host]

Yeah.

[Caller]

Yeah, I am.

[Co-host]

Because she loves him for who he is, so.

[Host]

Hey, wait a second. It's no different than any other woman changing a man. This is no different.

[Co-host 2]

She's just saying it out loud and we're getting offended. Same reason people get mad at Simon.

[Caller]

We change you guys. That's what we do.

[Host]

And it goes both ways, so. Totally goes.

[Co-host 2]

So tell us how you tell. You tell us how you presented the ultimatum to him and tell us how he responded to it.

[Caller]

I made him a really great dinner. I sat him down, and as we were eating the dinner and drinking some wine, I just said, you know, Ryan, it's been three months. Things are really good between us, and I want this to continue. And Valentine's Day is coming, and I want you to ask me to marry you or just don't call me anymore. How long ago did you say give him this ultimatum? Was last week.

[Host]

Oh, my God.

[Co-host]

Oh, my God.

[Host]

A week? Come on now. We're unfair as this.

[Caller]

You really don't think so?

[Co-host 2]

No. Well, how did.

[Caller]

Men need a push? They need a push.

[Host]

After three months, you're pushing them right out the door.

[Co-host 2]

How did this less than average looking fella respond to your ultimatum?

[Caller]

Well, he didn't really say anything. You know, for a few minutes, he just kind of took it in, and then he said that he didn't want to discuss it until. Until Friday, until Valentine's Day, and that we would discuss it then.

[Co-host 2]

So do you think. Did you take that information that he gave you to mean that on Valentine's Day he's gonna come up with a ring?

[Caller]

I definitely do.

[Host]

And you're serious about this? If he doesn't come up with the ring, then you are dumping him the next day?

[Caller]

Yes.

[Co-host 2]

Do you have plans yet for Valentine's Day? Or you guys have a dinner planned? Or are you hanging out? Are you going out? What are you doing for Valentine's?

[Caller]

I'm gonna cook here.

[Host]

Well, we'll give you a reservation at Blue Point if we can record it. Hi. Q100. Good morning.

[Caller]

Good morning.

[Host]

Good morning.

[Co-host 2]

Good morning.

[Caller]

Hi. I'm sorry. I didn't know I was on.

[Host]

What's up?

[Caller]

Okay. I actually gave my husband now an ultimatum to marry me. It was, I guess, two and a half years ago on Valentine's Day. I told him that he needed to propose to me by May 1st or he's gonna have to wait five years for me to get out of school because I wanted to get my master's. Well, he actually did it on April 28th and completely surprised me. So it actually worked. I actually gave him an automaton and he did it.

[Host]

Yeah, it worked on me, too. What it made me think is just like, okay, what is my life gonna be like? It just made me really think, what is my life gonna be like without this woman in it? And that thought scared the hell out of me, so.

[Co-host]

Well, I can. Like, you know, with Burton Stacey. I mean, you were asking her to move from one city to the other, and I can totally understand her position, like. Okay, well, you know what? If you're gonna ask me to sacrifice this and do this, then you're gonna have to let me know what's going on. My dad did, so I could totally understand that. Now, how long have y' all been. Were you dating before you gave him the ultimatum?

[Host]

A little less than three months?

[Co-host]

No, the.

[Host]

Because she just gave me the ultimatum. Oh, no, no, no. She's gone. Adrian's gone.

[Co-host]

I'm not thinking this would be a great marriage. I don't know.

[Co-host 2]

Have you ever given other aunt ultimatums, Lena?

[Caller]

Yeah, I did it once before.

[Co-host 2]

And how did. Well, obviously.

[Host]

Obviously. Yeah. How long were you dating that guy?

[Caller]

We've been together for six months.

[Host]

Six months. Before that.

[Co-host 2]

Was he a homely fellow, or was he up to your standard of appearance?

[Caller]

He was a little bit more physically attractive than Ryan.

[Host]

So the last boyfriend was. Yeah. All right, well, here's what we have to do. This is supposed to go down on Valentine's night.

[Caller]

Mm.

[Host]

All right. Will you call us? Or can we get your number to call you back on Monday?

[Caller]

Sure.

[Co-host 2]

And you can fill us in on whether or not he popped the question.

[Co-host]

Sure.

[Host]

Okay.

[Co-host 2]

Hold on.

[Host]

We're gonna get your info. Okay?

[Caller]

Okay.

[Host]

Okay. Now, that's the first part of that. Wait till you hear the second part. I'll play it for you. Next on the Best of the Bird Show. The Bird show. Dude, did you order the new iPhone 17 Pro got it from Verizon. The best 5G network in America. I never looked so good.

[Caller]

You look the same.

[Host]

But with this camera, everything looks better. Especially me. You haven't changed your hair in 15 years. Selfies check please with Verizon. Get the new iPhone 17 Pro.

[Co-host]

Designed to be the most powerful iPhone ever.

[Host]

Plus a new iPad and Apple One.

[Advertiser/Voiceover]

No trade in needed. Offer ends November 5th with a new line on Unlimited Ultimate Best 5G Swords.

[Host]

Route Metrics Data United States 1 2025.

[Advertiser/Voiceover]

All rights reserved. Additional trim apply for all offers. See verizon.com for details.

[Host]

New products to launch New people to develop, new goals to crush Workday Go is designed for small and mid sized businesses. By bringing HR and finance together on one AI platform, you'll have everything you need to think big, go big and grow big. And activation is fast. It takes just 30 to 60 business days to get you up and running. Simplify your SMB on an AI platform, you'll never outgrow Workday Go.

[Advertiser/Voiceover]

Hey, I'm Paige desorbo and I'm always thinking about underwear.

[Host]

I'm Hannah Berner and I'm also thinking about underwear, but I prefer full coverage. I like to call them my granny panties.

[Advertiser/Voiceover]

Actually, I never think about underwear. That's the magic of Tommy John.

[Host]

Same. They're so light and so comfy. And if it's not comfortable, I'm not wearing it.

[Advertiser/Voiceover]

And the bras? Soft, supportive and actually breathable.

[Host]

Yes. Lord knows the girls need to breathe. Also, I need my PJs to breathe and be buttery, soft and stretchy enough for my dramatic tossing and turning at night. That's why I live in my Tommy John pajamas.

[Advertiser/Voiceover]

Plus they're so cute because they fit perfectly.

[Host]

Put yourself on to Tommy John.

[Advertiser/Voiceover]

Upgrade your drawer with Tommy John. Save 25% for a limited time at tommyjohn.comfort. see site for details.