The Bert Show – Full Show PT 2: Wednesday, November 5

Podcast Host: The Bert Show Cast (Bert, Kristin, Abby, Cassie, Tommy, etc.)
Date: November 5, 2025
Podcast Theme: Authentic, humorous discussions on relationship drama, entertainment news, and personal stories, with interactive listener involvement.

Episode Overview

In this episode, The Bert Show digs deep into complex relationship issues, shares a powerful survival story, and investigates dating dynamics with real listeners calling in. The cast maintains their signature candid, light-hearted but probing tone as they tackle themes of unconventional marriage arrangements, infidelity, resilience in health crises, and the intricacies of modern dating.

Segment Breakdown & Key Insights

1. "My Husband Isn’t the One Getting Me Pregnant" (01:45–11:15)

Key Discussion Points

• Jessica’s Unconventional Arrangement: Jessica calls in to discuss her open marriage and unique plan to become pregnant, with her husband’s full knowledge and consent, via her ex-fiancé rather than her husband.

  • She and her husband both have fertility issues.
  • Cost and openness led them to prefer intercourse with her ex-fiancé over sperm donation clinics.
  • The marriage is openly non-monogamous, with permission-based extramarital activity.

• Perspectives & Tensions:

  • The hosts express shock and try to understand the motivations, emotional boundaries, and rules of Jessica’s arrangement.
  • Callers weigh in—one shares that growing up in an open marriage environment was traumatic (06:01), experiencing an eating disorder and trust issues.
  • Another caller (Kate) disapproves strongly, questioning Jessica's suitability as a parent (06:36).

• Jessica’s Defense:

  • Jessica insists sex is just sex, and she would never "make love" to anyone but her husband (06:59).
  • She claims transparency will be maintained with the child about parentage.

Memorable Quotes

• “You’re sleeping with this ex-fiancé, huh?... Because there’s such a thing as, you know, a donor without having to have sex with them.” — Host (02:53)
• “My only rule is that… he can’t make love to this girl, whoever she is. It’s got to be strict, you know, passionate, wild, hot monkey sex.” — Jessica (05:15)
• “Sex is just sex, you know.” — Jessica (06:27)
• “How do you teach your child about a committed relationship when you guys are living the lifestyle that you’re living?” — Host (06:53)
• “We will explain… that Mommy and Daddy couldn’t have a baby together, so somebody else helped Mommy make the baby. But your daddy is your daddy.” — Jessica (06:59)

Timestamps for Key Moments

• (01:45) Jessica introduces her situation
• (03:01) Rules of the open marriage explained
• (06:01) Ashley shares the impact of her parents' open marriage
• (06:36) Callers weigh in — strong disapproval
• (08:22) A supportive caller offers an alternative perspective

2. Second Date Update: Velvet Room Mystery (11:16–18:09)

Key Discussion Points

• Robin’s Dating Dilemma: Robin recounts a magical night out with Jerry, full of chemistry and long conversations, but hasn’t heard from him since (12:21).

  • She suspects something must have gone wrong as Jerry did not offer his own contact info.

• Investigation Live On-Air:

  • The hosts reach Jerry live; he is evasive, claims to just be “taking his time,” but his quiet voice and abrupt behavior raise suspicions.
  • The hosts and listeners suspect Jerry has a girlfriend or wife.

• Confirmation & Fallout:

  • The show calls Jerry back; a woman answers and instructs them not to call again, confirming suspicions about Jerry’s duplicity (17:22).
  • Robin receives support from callers, is advised to move on.

Memorable Quotes

• “If you can look good under Waffle House light, then you can look good under any light, right?” — Host (12:32)
• “Don’t even waste the time. He’s so sneaky. So not worth it.” — Listener (16:37)
• “Don’t call me again.” — Jerry’s significant other (17:22)

Timestamps for Key Moments

• (11:32) Robin introduces her story
• (13:01) Show sets up to contact Jerry
• (14:09) Jerry takes the call, acts suspicious
• (17:22) Second call, woman answers and shuts down

3. The Miracle of Ms. Peach (18:11–28:46)

Key Discussion Points

• Peach’s Incredible Survival Story:

  • Two years prior, Peach was given 6 months to live due to lupus and cirrhosis, needing expensive home healthcare funded by Jay Mohr.
  • She recounts surviving “outliving hospice”—a rarity.

• Attributing Her Recovery:

  • Peach credits the financial help, reduced stress, positive energy, and change in mentality for her unexpected bounce-back to health.
  • She now lives independently, is happy, and encourages listeners to embrace optimism.

• Philosophical Take:

  • Peach is deeply thankful, refuses to worry about a relapse, and emphasizes living for the day.
  • She addresses skeptics by pointing to those who witnessed her decline and recovery.

Memorable Quotes

• “Can you spell miracle?... I really think that is just miraculous.” — Peach (20:55)
• “My illness had engulfed me emotionally and mentally... I had to start living my life.” — Peach (26:02)
• “When I wake up in the morning, I say, 'please help me through this day.' And when I go to bed at night, I say, 'thank you for giving me this day.'” — Peach (26:57)

Timestamps for Key Moments

• (18:58) Peach joins the call, updates on her health
• (20:09) Explains transition off hospice, Jay Mohr’s aid
• (22:27) Describes regained independence and gratitude
• (23:22) Confronts skepticism about her “miracle”
• (25:45) Emphasizes importance of positive mental attitude

4. Interview: “Dave,” the Serial Cheater (28:47–40:32)

Key Discussion Points

• Dave’s Confession:

  • Dave boasts about managing a wife in Boston, a girlfriend in New York, and another in Atlanta, all without their knowledge.
  • He explains his “system”: different phones, unlisted numbers, rotating pet names, and tight control of information.
  • He presents himself as a provider, likening himself to FDR, suggesting infidelity doesn’t preclude being a good man.

• Amoral Rationalization:

  • Dave expresses little remorse, insists the women are “happy,” and claims it’s about fulfilling everyone’s needs.
  • He rationalizes secrecy as necessary to avoid financial and familial consequences.

• Ethical and Female Listener Backlash:

  • Hosts and callers challenge Dave, questioning his values, the emotional consequences, and pointing out the hypocrisy that his wife could easily be duplicating his behaviors.
  • One caller, emotional and angry, wishes severe consequences upon Dave.
  • The debate extends to the nature of monogamy and honesty in relationships.

Memorable Quotes

• “You control what they know, what information they have access to. So I have a cell phone in each city... as far as they know, I’m the man.” — Dave (30:26)
• “So it’s just all one big game... None of your life is real.” — Host (34:23)
• “Why don’t you just tell them?”... "The laws in the state of Massachusetts would take half my stuff... So what she doesn’t know isn’t hurting her." — Dave (35:03 & 35:09)
• “When your son comes up to you, are you going to sit him down and tell him exactly what you did?... Live for the moment. Yeah.” — Host and Dave (36:50; 37:01)

Timestamps for Key Moments

• (29:52) Dave’s introduction
• (30:26) Dave explains his secret-keeping system
• (33:32) Tips on avoiding being caught
• (35:03) The show challenges Dave on his secrecy
• (36:31) Questioned about teaching these values to his son
• (37:14–39:06) Emotional caller feedback and monogamy debate

Additional Notable Moments

• Listener Engagement: Throughout, listener call-ins provide raw, diverse perspectives, reinforcing The Bert Show’s interactive format.
• Recurring Topics:
  • The challenges of trust, honesty, and communication in relationships.
  • Impact of adult relationship choices on children.
  • Resilience in the face of dire health predictions.

Episode Impact & Takeaways

• Diverse Perspectives: The episode covers a wide range of relationship arrangements—from open marriages to deceitful double/triple lives—and brings in real voices impacted by these choices.
• Honesty vs. Secrecy: Candid discussions highlight how honesty (or lack thereof) shapes both romantic and familial relationships.
• Survival & Positivity: Peach’s story offers an uplifting counterbalance, suggesting the transformative power of community support and a positive mindset.

Notable Quotes by Timestamp

• Jessica on open marriage:

  • “You have to ask permission.” — (03:54)
  • “Sex is just sex, you know.” — (06:27)

• Ashley (listener, on open marriage impact):

  • “It affected me bad. I become bulimic.” — (06:01)

• Peach (on recovery):

  • “Can you spell miracle?... I really think that is just miraculous.” — (20:55)
  • “All I have is today.” — (24:28, 26:57)

• Dave (serial cheater):

  • “You control what they know... as far as they know, I’m the man.” — (30:26)
  • “What she doesn’t know isn’t hurting her. So why hurt her?” — (35:09)

Recommended For

Listeners curious about real-world relationship challenges, open communication, and personal transformation will find this episode engaging, provocative, and at times deeply moving.