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?