The Bert Show – Full Show PT 3: Monday, January 26 [Vault]

Date: January 26, 2026
Podcast Host: Pionaire Podcasting
Main Cast: Bert, Kristin, Abby, Cassie, Tommy, and more

Episode Overview

This episode is a lively segment of The Bert Show where the cast dives into stories about complicated engagements, commitment issues, and ambitious New Year’s resolutions—with a comedic twist and plenty of open, candid discussion from the hosts and callers. The show balances outrageous personal stories with interactive segments, inviting listeners to share, react, and sometimes commit to wild on-air challenges. Notably, they introduce the concept of "motivation by humiliation": participants risk getting a literal tattoo if they fail at their New Year’s resolution.

Key Segments & Discussion Points

1. Angela’s Wild Engagement Saga

(00:00–16:44)

Segment Summary:

• The recurring guest "Angela" calls in to elaborate on her unprecedented romantic entanglements—having been engaged to three men at the same time.
• Discussion unfolds around Angela’s motivations, honesty, and feelings about relationships, gifts, and marriage itself.
• Callers weigh in, questioning her sincerity and morality; Angela defends her actions, claiming honesty (at least with herself) and arguing she just needs to clarify her feelings before settling down.

Key Moments & Quotes:

• Angela discloses:
  Angela: “No, it wasn't two. Sorry. It was three.” (00:31)
• Host Bert’s curiosity:
  A: "The thing that I find so interesting about you is, you know, all of this is so wrong, yet you’re so callous about it, and you really, like, can go from guy to guy and you really don’t care." (05:55)
• Angela’s justification:
  C: “First of all, I didn’t go from guy to guy. He came to me.... If he knows that I’m already engaged and he’s willing to wait for me to work it out, it is not my fault.” (06:06)
• On receiving lavish gifts:
  C: “He gave me a diamond tennis bracelet from Tiffany's and he got me little diamond style tears. ... For Christmas I got a Wii with all the freaking accessories.” (03:39)
• Angela’s honesty with her fiancé:
  C: “My current fiancé ... knows I’m hanging out [with the ex], he just doesn’t know he asked me to marry him, and I’m going to tell him.” (08:21)
• Angela’s existential crisis:
  C: “What if my wedding day comes, right? And I am walking down the aisle, and I see my high school sweetheart in the audience, and all of a sudden I am filled with, oh, my God, what would have happened?" (15:23)

Listener & Host Responses:

• Other callers and hosts alternate ridicule, psychoanalysis, and disbelief, with many suggesting Angela is motivated by gifts or the drama of relationships, not genuine love.
• One caller, Stephanie, accuses Angela of being “a narcissistic, delusional liar.” (08:44)
• Multiple times, hosts press Angela on who she actually intends to marry; Angela wavers, stating her deep feelings for both men and admits to being overwhelmed by the “celebration” aspect of engagements (13:09–13:18).

2. “Motivation By Humiliation”: The Tattoo Challenge

(16:46–32:48)

Segment Summary:

• The cast launches a memorable New Year’s challenge: if a participant fails to achieve their New Year’s resolution, they must get a tattoo visibly marking their failure.
• The idea is to invoke both motivation and public accountability—if you don’t quit smoking, lose those pounds, or get married, you wear your defeat for life.

How It Works:

• The show recruits listeners willing to participate, explains the legalities, and discusses tattoo placement.
• Incremental progress is considered ("milestone tattoos" if people partially succeed, e.g., quitting for a while but not the whole year).

Key Moments & Quotes:

• Bert on the challenge:
  A: “We want to motivate you by humiliating you if you do not conquer your New Year’s resolution this year. And we've hired a professional tattooist that is willing to tattoo you if you don't do your resolution with something that basically says, I couldn't fulfill my resolution.” (18:32)
• Callers volunteer for the challenge:
  • Lisa: “I have to quit smoking once and for all... I’ve only not quit, probably because it’s tough and I’m lazy, but I got to do it." (22:47)
  • Hosts clarify tattoo must be in a visible place; Lisa suggests the ankle, which is debated (24:21–24:47).
• Beth’s commitment:
  Beth: “About three years ago, I started the Depo Provera birth control shot, and I gained almost 50 pounds in about four weeks. ... I have to lose between 40 and 50 pounds by my one year anniversary in September.” (27:02)
• Tattoo consequences:
  Bert: “You are willing to put a tattoo on that says, I couldn’t lose the weight.” (28:26)
• Sarah volunteers both herself and her fiancé:
  F: “We're gonna get married this year. We've been engaged almost two years now. We have a child together. ... The tattoo that you guys would get at the end of the year if you are not married would be, we couldn't commit. Or he would put, I just can’t commit.” (31:06)
• Hosts joke about tattoo slogans:
  E: “Should say even getting knocked up didn’t work.” (32:28)
  A: “And you have to explain that to every woman that he ever sees without a shirt on ever again.” (32:41)

3. Notable Quotes and Memorable Moments

Angela’s Forthrightness:

• “What do you think I said? This is Angela, the black widow here.” (05:00)
• “If you don’t want us to make you sound bad, we’ll take calls.” (08:20)

Hosts on New Year’s Resolutions & Failure:

• “You are permanently stating publicly that I will get the ink on my arm or wherever that says I could not do this.” (19:21)
• “If you don’t accomplish your resolution, then you get the tattoo. ... We’re gonna make you sign paperwork.” (20:11)

On Gifts & Relationships:

• “Why would she end the celebration of her—” “That’s true.” (08:12–08:14, playful sarcasm about Angela’s love of gifts)

Playful Analysis from the Team:

• "You just want to clone the good parts of both of them, meld them together, and then that's the guy you'll marry." (13:00)
• “I’ve quit countless times. But it is after. For me, it’s most difficult after about three weeks or a month when I start to fall apart.” (25:09, Lisa on her struggle to quit smoking)

Timestamps for Major Segments

• 00:00 – 16:44: Angela’s engagement saga, listener reactions
• 16:46 – 26:41: Introduction and deep-dive into the “motivation by humiliation” tattoo challenge, including listener Lisa’s and Beth’s pledges
• 26:41 – 32:48: More tattoo challenge volunteers (including engaged couple), wrapping up calls and humorous banter about tattoo slogans

Takeaways

• The Bert Show delivers its signature blend of outrageous personal stories, humor, tough love, and interactive listener engagement.
• Angela’s multiple engagements spark both comedic disbelief and real talk about relationships, gifts, honesty, and self-awareness.
• The tattoo-based “motivation by humiliation” is an innovative take on making New Year's resolutions stick—with public accountability, high stakes, and plenty of laughs and empathy for the challenges of self-improvement.

Listeners are left eagerly awaiting follow-ups with all participants, especially Angela and the tattoo challengers. The tone is playful but real—mixing empathy with hilarity—making for a radio segment as unpredictable as it is entertaining.