The Bert Show – Full Show PT 2: Tuesday, October 28 [Vault]

Date: October 28, 2025
Podcast Host: Pionaire Podcasting
Primary Hosts/Voices: Bert (Adam), Kristin (Lindsey), Jeff, Cassie, Tommy, Tracy, Knox, Christian
Special Guest: Cher

Episode Overview

This vibrant and comedic episode of The Bert Show brings listeners a mix of deeply personal stories, dramatic listener moments, playful dating banter, and a star-powered guest interview with Cher. The cast’s authentic, conversational style immerses the audience in everything from "War of the Roses" relationship drama to surprisingly candid medical anecdotes, a heartfelt discussion with Cher about her music, life, family, and legacy, and some classic Bert Show dating dilemmas with intern Tracy.

Key Segments & Highlights

1. War of the Roses: Cheating Drama with a Family Twist (01:44–05:56)

• Summary:
  The classic “War of the Roses” segment: Autumn suspects her boyfriend Christian of cheating and sets up a flower delivery test live on air. The twist? Christian sends the roses to April—Autumn’s 18-year-old sister.
• Key Moments & Quotes:
  • Lindsey (posing as florist): "Who would you like to send the roses to?"
  • Christian: "Let me send it to April." (02:52)
  • Autumn’s confrontation is raw and emotional, exposing a jaw-dropping betrayal.
  • Autumn: "That is my 18 year old sister. A guy who's practically half your age … you should have just told me about this. You didn't have to go by my back. And my sister." (03:40)
  • Christian: "It's over, Christian, in case you hadn't noticed." (04:21)
  • Host’s empathy:
    • Adam: "Sometimes, just… closure, you know, will help you out." (05:25)
    • Christian: "It's better to know who you can trust and who you can't. So this is a hard lesson" (05:34)
• Takeaway:
  A shocking segment balancing radio drama with real emotional fallout, ending with empathy and some awkward humor.

2. Unfiltered Medical Confessions: The "Booty Region" Anxiety (05:58–11:15)

• Summary:
  Adam confides in the team about his anxiety over getting prostate exams, tracing his discomfort back to a childhood medical issue (rectal atresia).
• Key Moments & Quotes:
  • Adam: "Mine happens to be thy whole booty region ... I have to go in for the full on check up again today." (05:58)
  • Adam’s childhood ordeal: "I was born with a really, really teeny rosebud and my dad had to stretch it with his pinky every night when I was a kid in order for me to poop." (06:29)
  • The team offers comic relief, joking about the gender differences in medical exams:
    • Jeff: "It's because women don't have prostates." (06:22)
    • Lindsey: "Gynecological exams are probably the most painful there is … They crank it all open ... the jaws of life inside you." (08:12–08:24)
  • The story becomes a group riff, leaning into the show's trademark balance of cringe, laughter, and group support.
• Notable Quote:
  • Jeff: "I think you can make the promise never to mock someone until they share the story of their dad's digit in your ass." (10:21)

3. Cher Interview: Fame, Family, and Fierce Individuality (11:15–21:49)

(Segment starts with Jeff’s introduction and spans a range of personal and career topics)

Key Discussion Points & Insights

• Cher’s Early Years

  • Story of her wedding band: Found by chance, leading to a fan returning it to her.
    • Christian: "It was in the dirt ... he picked it up and threw it in his pocket." (11:49–12:17)

• Meeting Sonny Bono

  • Dispels rumors: Sonny was not a meat delivery man when they met, but a music promoter.
  • First impression: "I have to say, I was just mesmerized. He had a Caesar haircut … and beetle boots on. … I just was fascinated with him." (13:28–13:56)

• Sonny Bono’s Death and Eulogy

  • Cher reflects on the grief and her lack of experience with loss:
    • Christian: "I was completely unprepared for it, and I'd never had that feeling before." (14:01)

• Enduring Fame & Reinvention

  • Discusses longevity in show business:
    • Christian: "I think it's luck. I don't have any answers … sometimes people, you've just been around for so long, and people just know everything about you." (16:02)

• Media Scrutiny and Privacy

  • Christian: "Sometimes it's, like, about the tabloids that they won't leave me alone...sometimes I just go away, and you don't hear about me...then when I'm ready, I come back." (16:41–17:04)

• Candid Discussion on Daughter Chastity (Chaz) Coming Out

  • Cher describes the challenge of learning her child was gay and surprising herself with her initial reaction, despite lifelong LGBT support.
    • Christian: "You really are called to believe what you...you really have to know that you believe what you say you believe. … It took me a while ... honestly." (18:26)
  • Advice for others:
    • Christian: "For the kids, I would break it to the person in your family that you think is going to be the most receptive and then work backwards." (19:12)
    • Christian: "For parents ... you have to remember that you really love your children, and they are basically the same people, and they really need your support." (19:35–20:09)

• Cher and the Gay Community

  • Christian: "Gay guys either like you or they don't. … there's something else that happens. … I'm not so sure that's enough." (20:12 – 20:35)

• Rapid-Fire “True or False” and Career Reflections

  • Thelma and Louise: Was offered the film, but turned it down:
    • Christian: "Yeah, I actually turned it down because I didn't like the ending. So that was really stupid." (20:38)
  • Dyslexia: Confirmed, but managed thanks to a photographic memory.
    • Christian: "I have to read really slowly. But once I read something, I pretty much can commit it to memory." (20:51–21:10)
  • Napster: Bad for the industry; felt like “the rug pulled out from under you.” (21:13–21:14)

• Still Thrilled by Hearing Her Songs on Radio

  • Christian: "I'm always thrilled. I mean, I always get excited when I hear a song on the radio." (21:37)

4. Dating Segment: Tracy's Band Guy Crush (22:19–30:22)

• Summary:
  Intern Tracy reveals her long-standing crush on a guy in a band. The segment mixes advice, playful teasing, and dating strategy.
• Key Moments & Quotes:
  • Adam’s sports analogy: "This is like the super bowl of dating for her." (23:27)
  • Tracy on her attraction: “She will not look at a guy unless he has a guitar in his hand. Drumsticks ... that'll work too.” (22:57 – 22:59)
  • The big letdown: The long-awaited date is postponed because the guy claims to have the flu, though he proposes future plans.
  • Host’s advice:
    • Adam: "I think what you have to do is ignore him. I think you have to totally keep him on his toes and make him chase you." (29:12)
    • Tracy: "I'm totally into games. ... I'm not gonna call you back every time you call me, and I don't call guys. Usually they have to call me, keep them on his toes." (30:03–30:14)
    • The crew humorously discusses playing “hard to get” and even joke about ego-boosting for radio personalities.
• Takeaway:
  A lighthearted, relatable exploration of modern dating dynamics, delivered with trademark Bert Show wit and teasing.

Notable Quotes (With Timestamps)

• "That's your sister?"
  — Adam, in shock as Christian names his girlfriend’s sister for the flowers. (03:38)

• "It's better to know who you can trust and who you can't. So this is a hard lesson, but..."
  — Christian (the scorned girlfriend), reflecting on being cheated on. (05:34)

• "I was born with a really, really teeny rosebud and my dad had to stretch it with his pinky every night when I was a kid in order for me to poop."
  — Adam, on why he dreads prostate exams. (06:29)

• "I was just mesmerized ... he had beetle boots on ... I just was fascinated with him."
  — Cher (Christian), on meeting Sonny Bono. (13:28–13:56)

• "You really are called to believe what you...you really have to know that you believe what you say you believe. ... it took me a while, honestly."
  — Cher (Christian) on accepting her child coming out. (18:26)

• "For parents ... you have to remember that you really love your children ... they really need your support."
  — Cher (Christian), on advice for parents. (19:35)

• "I think it's luck. I don't have any answers for that because I'm amazed myself."
  — Cher (Christian), on sustaining her career. (16:02)

• "Gay guys either like you or they don't … There's something else that happens."
  — Cher (Christian), on her gay icon status. (20:12)

• "She will not look at a guy unless he has a guitar in his hand. Drumsticks ... that'll work too."
  — Adam & Tracy, on Tracy’s dating type. (22:57-22:59)

Important Timestamps

• 01:44–05:56 – War of the Roses: Infidelity scandal and aftermath
• 05:58–11:15 – Adam’s medical confession/prostate anxiety story
• 11:15–21:49 – Interview with Cher: her career, relationships, family, and industry insight
• 22:19–30:22 – Tracy’s dating woes and advice segment

Tone & Style

The Bert Show’s trademark blend of realness and goofiness runs through the whole episode, balancing dramatic revelations, candor, and humor. The interview with Cher is respectful and probing yet maintains a conversational and playful style. The camaraderie among the hosts is warm but laden with tease and comic relief—even in moments of sincere vulnerability or heartache.

Summary Takeaways

• Dramatic Listener Stories: War of the Roses delivers a jaw-dropping cheating twist that is both shocking and oddly cathartic for everyone involved.
• Vulnerability as Comedy: Adam’s medical woes are aired unfiltered, allowing humor to diffuse embarrassment and foster connection.
• Celebrity Depth: Cher’s interview covers everything from love and loss to the intricacies of public and private identity, offering sage advice on acceptance and survival in the spotlight.
• Everyday Dating Dramas: Tracy’s dilemma is a familiar, light-hearted tale of crushes, delays, and how to be (or not to be) "hard to get."

This episode encapsulates why The Bert Show is so beloved: real stories, celebrity access, and genuine laughs, always inviting listeners into their irreverent, supportive world.