The Bert Show

Episode: Vault: War of Roses - Diane & Doug
Date: November 5, 2025
Podcast Host: Pionaire Podcasting
Cast (in this episode): Bert (Host), Diane (Caller), Doug (Husband), Lindsey (Fake Florist), Jeff Bridges (guest commentator)

Episode Overview

In this classic “War of the Roses” segment, Diane suspects her husband Doug is cheating — especially given his suddenly vague behavior and a history of unfaithfulness early in their relationship. The Bert Show team helps Diane by setting up a faux flower delivery to see if Doug will send roses to her or another woman. What follows is a mix of tension, awkwardness, and some unexpected emotion, all navigated with the Bert Show’s trademark blend of empathy and light-hearted ribbing.

Key Discussion Points and Insights

1. Diane’s Suspicion and Her Story

• Diane shares her concern that Doug, her husband of 12 years, may be cheating again, as his recent behavior has grown distant and secretive.
  • “We got married, we were 18. I’m 30 now... Normally he’s very attentive and you know, polite and takes me out. But recently he’s just been not how he usually is. Like, he forgets to tell me things…” (Diane, 02:38)
• Specific incident: Diane recalls a recent Saturday when Doug was unreachable and had a suspicious story about a flat tire.
  • “I looked at his car and you know what? It could have been true or it could have not, but I don’t really know…” (Diane, 03:25)
• Diane reveals Doug has cheated before, in the very early stages of their relationship.
  • “He cheated on me once before… probably like 13 years ago… and that’s kind of how I knew.” (Diane, 03:08)
• Personal context: Diane is three months pregnant, adding to her emotional stress and self-doubt about whether hormones are fueling her fears.
  • “I don’t know if it’s maybe like hormones… I still take care of myself…I don’t know if I’m feeling, like, extra sensitive or…” (Diane, 04:22)

2. The Bert Show Panel Weighs In

• Bert sympathizes with the challenge of bringing up tough topics in long relationships.
  • “If you’ve been this guy for 12 years, then it seems like these are things that you should be able to bring up...” (Bert, 04:05)
• Jeff Bridges supports Diane’s intuition:
  • “You know what? If you have a doubt, you have a doubt. You know what I mean? And obviously, from what you’ve said, he is acting differently and you just want to know why.” (Jeff Bridges, 04:14)

3. The War of the Roses “Sting”

• Plan: The show calls Doug, posing as a florist offering a dozen free roses. Diane is silent on the line per the show’s rules.
  • “Hopefully it’s going to be back to you. OK? And the only thing that we ask is that you don’t say a word…” (Bert, 04:54)

4. The Call to Doug (War of the Roses Segment)

• Lindsey, pretending to be from “Fertile Flowers,” pitches the free roses.
• Doug’s skepticism: “What’s the catch?” (Doug, 05:52)
• But, reassured, Doug decides to participate.
• Crucially, he sends the roses to Diane:
  • “Send them to Diane.” (Doug, 06:32)
  • Card message: “With all my love. Always, Doug.” (Doug, 06:37-06:40)

5. Revelation and Aftermath

• Bert and Lindsey reveal the ruse.
  • “Hey, Doug. Hi, this is Bert and that was Lindsey. And we’re calling from radio station Q100.” (Bert, 06:42-06:44)
• Doug immediately suspects a setup:
  • “I knew something was going on….Nothing’s free.” (Doug, 06:48–06:54)
• Bert explains Diane’s fears:
  • “Diane’s mind’s been kind of going a little crazy these days... she just wanted to make sure she was the only woman in your life.” (Bert, 07:01–07:05)
• Diane tries to cover up her suspicion, backpedaling the real reason:
  • “No, I just. Sweetie, I just called because they said that they would give us free flowers.” (Diane, 07:20)
• Doug feels insulted by the implications:
  • “You guys are being a little rude here. I think you’re insulting my relationship here. Baby, I think you should hang up the phone.” (Doug, 08:57-09:07)

6. Concluding the Call

• The situation grows awkward, with both Diane and Doug eager to leave the conversation.
• Bert wraps things up with an embarrassed apology.
  • “Why don’t we all go? How’s that?... Our bad. Sorry about that.” (Bert, 09:09–09:11)
  • “Yeah, see ya. I’ll call you later.” (Diane, 09:12)

Notable Quotes & Memorable Moments

• Diane’s uncertainty:
  • “I don’t know if I’m feeling, like, extra sensitive or. I don’t know, it’s just. It’s been really difficult.” (Diane, 04:22)
• Bert’s empathetic nudge:
  • “If you’ve been this guy for 12 years, then it seems like these are things that you should be able to bring up…” (Bert, 04:05)
• Jeff Bridges on doubt:
  • “If you have a doubt, you have a doubt. You know what I mean?” (Jeff Bridges, 04:14)
• Doug’s simple, heartfelt card:
  • “With all my love. Always, Doug.” (Doug, 06:37–06:40)
• Doug’s defensiveness:
  • “You guys are being a little rude here. I think you’re insulting my relationship here.” (Doug, 08:57)
• Awkward wrap-up:
  • “Why don’t we all go? How’s that?... Our bad. Sorry about that.” (Bert, 09:09)
  • “Yeah, see ya. I’ll call you later.” (Diane, 09:12)

Important Segment Timestamps

• [02:27] Diane explains her suspicions and background with Doug.
• [04:22] Diane reveals she’s three months pregnant.
• [05:33] Lindsey makes the flower “offer” call to Doug.
• [06:32] Doug chooses to send roses to Diane.
• [06:37] Doug’s message: “With all my love. Always, Doug.”
• [06:44] The Bert Show reveals the setup.
• [07:16] Diane backpedals the real reason for the call.
• [08:57] Doug expresses frustration with the show’s intrusion.
• [09:09] The show quickly winds down and apologizes.

Tone and Atmosphere

The episode swings between tense and tender, with lots of awkwardness as the setup unfolds. The show hosts are sympathetic but also irreverent, trying to inject humor and kindness in a sensitive situation. Diane, initially anxious and vulnerable, becomes almost comically evasive once the truth is out, while Doug is bewildered and quickly defensive.

Takeaways

• Diane’s anxieties stem from real past hurts, but Doug’s loyalty is ultimately reaffirmed.
• The “War of the Roses” formula leads to an awkward but revealing moment about trust and communication in relationships.
• Both parties leave the situation a bit bruised and embarrassed, but the hosts provide levity and a soft landing.

This summary reflects the narrative and emotional arc of the episode, providing listeners with context, key developments, and memorable dialogue, while retaining the show’s candid and quirky style.