The Bert Show - Full Show: PT 3 Tuesday, November 4 [Vault]

Date: November 4, 2025
Host: Pionaire Podcasting
Cast: Bert, Kristin, Abby, Cassie, Tommy, Jeff, and others

Episode Overview

This episode of The Bert Show brings the signature mix of humor, real talk, and listener participation. The cast delves into several engaging topics: the power of Olympic athlete montages in storytelling, a listener’s plea for relationship advice after infidelity, a candid interview with CNN’s Dr. Sanjay Gupta about sleep issues and medication, and a lively debate about whether teenagers should babysit. The show maintains its playful, authentic tone while also providing moments of heartfelt reflection and practical takeaways.

Major Segments & Discussion Points

1. The Art of the Olympic Montage

[01:29 - 06:18]

Theme:
The cast jokes about the Olympic Games’ shift from being about athletic competition to being dominated by emotionally charged athlete montages.

Key Insights:

• These montages are now a staple of Olympic coverage, aiming to make viewers emotionally invested in the athletes.
• The team parodies this format, creating a funny mock-montage about Jeff Dollar’s imaginary Olympic journey, escalated with increasingly absurd achievements.

Notable Quote:

• “It's the gripping stories to get you invested in the... because you want to be cheering for that person... And you need to know that when they were six years old is when they first broke their legs in some kind of random accident.” — D [01:41]

Memorable Moment:

• Jeff’s Olympic montage featuring accomplishments like “gold medaling in Cold Stone Creamery flavor picking” and his journey through “BlackBerry Biathlon.”

  “Just the mention of his name, Jeff Dollar echoes gold medal greatness in a multitude of sports.” — F [03:20]

2. Listener Dilemma: Can a Relationship Recover from Rock Bottom?

[06:19 - 25:18]

Theme:
A listener (“Jason,” voice disguised) shares his story of repeated infidelity in his long-term relationship. He wonders if anyone has made such a relationship work after “hitting rock bottom.”

Key Insights & Discussion Points:

• Jason’s girlfriend lied about a business trip, secretly traveling to the Virgin Islands with a coworker and leaving revealing notes.
• Despite his deep love for her, he’s uncertain whether trust can ever be restored.
• The hosts and listeners discuss whether it’s possible to rebuild trust after significant betrayal.

Notable Quotes:

• Bert: “I want to actually try to find somebody listening to your situation going, you think yours was bad? Here's where mine was at. I stayed in the relationship and maybe give you some insight on exactly what happened.” [13:29]
• Jason: “She's the love of my life. I mean, there's no doubt that I'm in love with her so I don't know if this will work out or not.” [12:01]
• Jeff: “It's not only him. Like, she has to be prepared that anytime he says, let me look in your briefcase, she has to let him, no matter what.” [20:01]

Listener Calls:

• Kimberly ([16:36]): Shares a story of her husband’s infidelity and drug addiction. She stood by him for her children, and after many years, he turned his life around.
• Patrick ([18:26]): Worked through suspicions and a breakup with his now-fiancée. The process of rebuilding trust took months, showing it can be done but requires effort from both sides.
• Jackie ([20:47]): Describes a complicated relationship involving infidelity and broken trust, but ultimately says she’s glad she stayed, even if the relationship remains work-in-progress.

Cast Reflections:

• The group largely advises Jason to move on, expressing skepticism that trust can truly be rebuilt given the lack of remorse shown by his girlfriend.
• The segment is punctuated by humor and resignation.
  “A lot of love to give, man… And you should get a puppy or a goldfish.” — B [23:47]
• Memorable humor: The hosts rattle off a string of old proverbs (“A stitch in time saves nine”; “Don’t take a wooden nickel”) as they wrap up.

3. Medical Spotlight: Sleep, Pills & Real Rest with Dr. Sanjay Gupta

[27:39 - 45:36]

Theme:
CNN’s Dr. Sanjay Gupta is brought on to talk candidly about sleep disorders, reliance on prescription medication, and the societal consequences of “quick fix” sleep solutions.

Key Discussion Points:

• Addictiveness of Sleeping Pills: Newer medications (like Lunesta and Ambien) are intended for short-term use, but dependence (physical or psychological) can still develop.
• Physiological effects: These drugs depress neurotransmitters, quickly initiate sleep, and usually don’t cause grogginess if used properly.
• Side effects: Rare cases like “sleep eating” on Ambien, and the surprisingly high recreational use among teens and young adults.
• Alternatives to Medication: Emphasis on improving “sleep hygiene” (blackout curtains, steady schedule, limiting pre-bed stimulation, etc.) before seeking prescriptions.
• Dangers of Sleep Deprivation: Links to chronic illness, memory impairment, and weight gain.
• Provigil & Stimulants: Questions about the safety of drugs that keep people awake (e.g., for shift workers or students); Dr. Gupta cautions about unknown long-term effects.

Notable Quotes:

• Dr. Gupta: “None of them are designed to be taken lifelong...They’re supposed to get you through periods of your life when you’re having difficulty sleeping, but then you’re supposed to come off of them.” [29:37]
• Dr. Gupta: “Lack of sleep...your cortisol levels are different than the average population. They have a likelihood of developing more chronic diseases such as sleep apnea, pulmonary diseases as well, and heart disease...” [41:21]

Listener Questions:

• Susan ([36:44]): Asks for advice on ending her dependency on Ambien; Dr. Gupta suggests gradual tapering.
• Aaron ([38:21]): Notes high schoolers are often seeking Ambien for recreational use, highlighting growing prescription drug culture among youth.
• Call about Provigil ([42:52]): Raises concerns about using “wakefulness” drugs as a workaround for poor sleep.

4. Debate: Should Teenagers Babysit?

[45:38 - 56:46]

Theme:
Inspired by a family debate, Bert takes a hard stance against hiring teenage babysitters, seeking stories to convince his wife that it’s a bad idea.

Key Discussion Points:

• Cast Banter: Lively, funny exchanges about their own teenage babysitting or babysitter experiences.
• Bert’s argument hinges on the risk of emergencies and teenage immaturity. Others counter that many teens are responsible, have training, and nothing catastrophic happened on their watch.
• Listener Calls: A mix of stories, ranging from harmless teenage mischief (sampling alcohol, inviting a boyfriend over) to true horror tales:
  • Alicia ([50:15]): Her sister became pregnant with her boyfriend while babysitting—with the kids present.
  • Jenny ([51:03]): Used to drink from the liquor cabinet while babysitting but never endangered the kids.
  • Sonya ([52:39]): Babysitter locked herself out with a toddler still inside; minor but anxiety-inducing.
  • Jolly ([53:49]): A 15-year-old sitter gave vodka to a 2-year-old, causing alcohol poisoning and ongoing medical issues.
  • Sarah ([56:02]): A 15-year-old babysitter’s negligence led to the house burning down.

Notable Quotes:

• Bert: “To put the most precious thing in your life in the hands of a teenager. Man, I know it's been done a trillion times over the course of history, but I just can't do it. I just absolutely can't do it.” [56:23]
• G (caller): “Don’t ever hire a child to watch your children. It's unfair. Because this little girl, she looked at me like… she's so sad… I'm supposed to feel bad for her because she's still a kid?” [55:12]

Memorable Humor:

• After several failed attempts to find a “shocking” story for his case, Bert exclaims, “So far, Bert, your theory sucks,” as the cast jokes about the survival of the kids as the only outcome that matters. [50:54]

Memorable Quotes & Moments

• On Olympic montages:
  “Once Jeff Dollar tasted Olympic greatness, his ego was hungry for more.” — F [03:48]

• On infidelity:
  “It's not only walking out the door, but... every little tiny thing that happens... in the back of your mind... And I just don't know. So you have to have the energy to be able to handle it and work through it.” — D [19:39]

• On sleep medication:
  “We're a quick fix society and we are subjected to the marketing, there's no question. But I think too many people in this country probably jump to the pill first before trying things that might be a little easier.” — Dr. Sanjay Gupta [30:49]

• On babysitting fears:
  “Can I see your CPR card?”... “Here’s how babysitter happened in our neighborhood: Hey, Dollar, you going anywhere this afternoon? All right. Make sure Josh doesn't set himself on fire.” — E [47:32]

Timestamps Cheat Sheet

• Olympic Montage Satire – [01:29 — 06:18]
• Listener Infidelity Dilemma – [06:19 — 25:18]
• Dr. Sanjay Gupta Interview: Sleep/Medication – [27:39 — 45:36]
• Teen Babysitter Debate – [45:38 — 56:46]

Conclusion

This episode of The Bert Show walks a fine line between humor and heartfelt advice. From lampooning Olympic storytelling to navigating the serious pain of betrayal, to investigating our society’s relationship with sleep (and the pills that promise it), and ending on a passionately one-sided debate about babysitters, the show is quintessential Bert Show: real, witty, and consistently engaging. Even on tough topics, the cast’s camaraderie and openness make for a relatable and entertaining listen.