The Bert Show – "Vault PT 2: Bad Ultimatum" (November 5, 2025)

Podcast by Pionaire Podcasting • Hosts: Bert, Co-host Lena, Jeff Bridges, Ryan

Overview

This episode revisits a dramatic relationship saga involving Lena, a woman who gave her boyfriend, Ryan, an early ultimatum: propose by Valentine’s Day or end the relationship. The show explores the fallout from the ultimatum and Lena's decision to discuss it on the radio – with both the couple and listeners weighing in. The team invites Ryan on air for his side, and the episode turns into a candid, at times brutally honest, conversation about relationships, public airing of private issues, and personal accountability.

Key Discussion Points & Insights

1. What Happened on Valentine’s Day?

• Lena recounts the aftermath of her ultimatum:
  • She dressed up, prepared the house and dinner, waiting for Ryan, but he didn't show up or even call.
    • “He didn’t come at all. No, he just didn’t show up.” (03:00 – Caller Lena)
  • Lena still maintains that men need a "push" via ultimatums and accuses the radio show of having contributed to the collapse.

2. Radio Responsibility vs. Personal Accountability

• Hosts push back on Lena blaming the show:
  • “You agreed to come on the radio… You said he’s not an attractive man. What guy is going to say, 'that’s the woman I want to marry?'” (04:06 – Co-host Lena)
  • The show emphasizes Lena’s own choices, especially her disparaging comments about Ryan’s looks on air.

3. Listener Calls – Brutal Honesty

• Several callers express little sympathy:
  • Keisha:
    • “Friday, I prayed that he did not call her ever again in life. And God do answer prayer. He got exactly what she deserved.” (04:56)
  • Tanya:
    • "She’s crazy. She’s blaming it on y’all. And she was the idiot who called in... I think she deserves every bit of it.” (05:13)
  • Laura:
    • “Even if your boyfriend is not the most beautiful…he should be beautiful to you. You supposedly want to marry [this] man.” (05:51)

4. Ryan’s Side of the Story

• Ryan’s recount of meeting Lena:
  • Casual start; met via mutual friends and dated for a few months
  • The ultimatum was abrupt and “totally caught [him] off guard.”
    • “She just said, ‘I’ve always dreamed of being asked to be married on Valentine’s Day…and that if you don’t, I just don’t see any reason for us to continue.’” (08:34 – Ryan)
  • Hearing Lena’s radio appearance convinced him to stay away.
    • “It’s a restraining order waiting to happen.” (07:51 – Ryan)

5. The Couple’s Dynamics and ‘Red Flags’

• Ryan reflects on their short relationship:
  • “We really hadn’t known each other that long…what are you going to know in three months?” (08:05 – Ryan)
  • Didn’t see obvious “psycho behavior” early but notes some minor incidents.
  • When pressed, Ryan describes the “love word” was more a casual thing tossed around—not serious.

6. Listener Support for Ryan

• Multiple calls support Ryan, critiquing Lena as “shallow” and a “gold digger."
• Lois:
  • “She’s a gold digger. That’s all there was to it. I don’t care what you look like…Let her cut your losses, honey. Keep your bank account intact.” (12:35 – Lois)
  • Offers moral encouragement based on her own long marriage.

7. Ryan’s Response and Forward Look

• Ryan maintains good humor about the situation, joking:
  • “Well, man, I may be ugly, but at least I don’t fart in my sleep.” (10:14 – Ryan)
• Hosts suggest setting up a dating account for Ryan.
  • “Now I’m single. That’s what I’m all about.” (13:53 – Ryan)

Notable Quotes & Memorable Moments

• Ultimatum Setup:
  "You need to propose to me by Valentine's Day. Our things are off." (02:15 – Host Burt paraphrasing Lena)
• Lena on Male Motivation:
  "The ultimatum is necessary for men because men need to be given a little push.” (03:41 – Caller Lena)
• Lena blaming the radio:
  "I think the radio is responsible for what happened." (03:10 – Caller Lena)
• Co-host pushback:
  "You agreed to come on the radio...You said he’s not an attractive man. What guy is going to say, 'that’s the woman I want to marry?’" (04:06 – Co-host Lena)
• Listener Keisha’s bluntness:
  "God do answer prayer. He got exactly what she deserved." (05:07)
• Ryan’s humor:
  "I may be ugly, but at least I don't fart in my sleep." (10:14)
• Lois’s advice:
  "Let her cut your losses, honey. Keep your bank account intact." (12:35)
• Moving on:
  "Now I’m single. That's what I'm all about." (13:53 – Ryan)

Timestamps for Key Segments

• Ultimatum recap and fallout – 02:15–04:35
• Lena blames the radio, hosts' reaction – 03:10–04:41
• Caller feedback (Keisha, Tanya, Laura) – 04:45–06:14
• Ryan’s perspective, relationship timeline – 06:35–09:14
• Ryan’s reaction to Lena’s radio appearance – 07:36–08:10
• Listener support and Lois's story – 12:31–13:34
• Ryan’s future – dating account idea – 13:41–14:22

Tone & Style

Lively, candid, and a little irreverent. The show mixes humor with direct honesty, both in the hosts’ banter and the listeners' unfiltered feedback. Ryan remains gracious and wryly funny, while Lena comes across as defensive under criticism. The show creates a cathartic, at times comedic, group therapy atmosphere for both its participants and audience.

In Summary

"Vault PT 2: Bad Ultimatum" is a quintessential Bert Show relationship drama, unfolding with real-time reactions, sharp listener calls, and a healthy dose of humility. The hosts ultimately drive home lessons about self-awareness, proportionality in relationships, and the risks of broadcasting personal drama. Ryan, far from the villain Lena described, wins listeners’ sympathy and a (hopeful) shot at better luck in love.