The Bert Show – Full Show PT 1: Monday, November 3 [Vault]

Airdate: November 3, 2025
Summary by an Expert Podcast Summarizer

Episode Overview

This episode of The Bert Show brings listeners a lively mix of engaging, real-life stories, listener call-ins, and unfiltered discussion. The cast—Burt, Kristin, Abby, Cassie, Tommy, and crew—navigate topics ranging from the most romantic gestures ever made, to the honest anxieties and dreams of singlehood and wedding planning, to the perils and awkwardness of blind dates. Balancing humor, warmth, and a good dose of skepticism, the team creates a space for listeners to share their lives and to weigh in on matters of the heart.

Key Segments, Discussion Points, and Insights

1. “Romance Poker” – The Epic Romantic Gesture Story Battle

[01:10–19:57]

Main Premise

The show opens with a tongue-in-cheek “dangerous game”—callers and hosts compete to share the most epic, memorable, or over-the-top romantic story. Each tale is measured against "Jeff's unbeatable story," progressively raising the bar through listener contributions.

Notable Romantic Stories (with Timestamps)

• Roses & Candlelight – [02:04]
  • Caller recalls her brother-in-law delivering roses with personalized notes across different stages of a first date, ending with a romantic homemade dinner and dancing on a lit-up porch.
  • “She was in forever. No wonder it’s brother-in-law.” – Jen [02:46]
• Tattooed Commitment – [03:29]
  • A caller describes her ex getting her name tattooed over his heart three months into dating—sparking a debate about grand gestures and prudence.
  • “That’s almost psycho.” – Jeff [03:54]
  • “He still has it.” – Caller [04:24]
• The Slow-Build Love – [05:22]
  • A listener recounts a relationship where "I love you" was said at three months, but they waited eight months for their first kiss, valuing emotional caution after past heartache.
  • “Are you sure he wasn’t having an outbreak?” – Jeff jokes, poking at the long wait [06:41]
• Coast-to-Coast Romance – [08:02]
  • Caller describes meeting her future husband over the phone in different states; they finally meet after months and are soon married.
  • “Love at first sound.” – Burt [08:36]

The Swing and the Portrait Story – [09:11]

• The show’s most compelling rival to Jeff’s tale is told: a couple shares a first “I love you” on a garden swing in college, a place immortalized by a custom portrait gifted at graduation, and the scene of his proposal.
  • “He hired artists to come and paint a portrait of the swing, which he gave me as my graduation gift and then proposed to me there a month later.” – Caller [09:49]

Jeff’s “Epic” Story Revealed – [11:01–14:29]

• The Plot: Jeff spins a dramatic, cinema-worthy narrative. His friend, during a fraught on-again, off-again relationship, books last-minute flights to New York, convinces his ex-girlfriend to join, sweeps her away (while she's dating someone else), then whisks her off from NYC to Paris for a week. After emotional twists and turns abroad, they return home, realizing they're right for each other (celebrating their 10-year wedding anniversary).
  • “He books two plane tickets for midnight to New York City… They get on a plane, go up to New York… He calls Air France and books two tickets to Paris.” – Jeff [12:04]
  • “This is the stuff that movies are made of.” – Jeff [10:46]
  • “The effort doesn’t matter, I guess, sometimes if it’s last minute or planned out way in advance. But just doing the work to make something happen…” – Jeff [10:20]
  • The debate: Does expensive spontaneity or thoughtful planning make for a better story?

Critical Analysis & Listener Reactions

• Planning vs. Spontaneity:
  • The team and callers dissect the romantic merits—some admire the spontaneous, big-scale gesture, others feel the swing story’s thoughtfulness resonates more.
    • “From the planning perspective, the swing story has a lot more that went into that than this one did.” – Jen [16:07]
• Ethics of ‘Stealing’ a Partner:
  • Some question if Jeff’s friend's story is truly romantic, given the girlfriend was seeing someone else at the time. Multiple listeners and hosts express discomfort, noting it might feel romantic only for the couple, not for the “other man.”
  • “If you’re her ex-boyfriend, yeah, this probably isn’t romantic.” – Jeff [14:39]
  • “It didn’t have deceit in the middle of it.” – Jason, caller [18:53]

2. “The Wedding Plan Book” – Amy’s Hyper-Prepared Single Life

[20:33–38:00]

Main Topic

Amy, a single woman who hasn’t dated in four years, confesses to having her wedding 100% planned—location, photographer, florist, even children’s names—just missing a groom.

Discussion Points

• Is This Planning ‘Crazy’ or Honest?
  • The show debates whether Amy’s pre-planning is actually uncommon or just unusually candid.
  • “I think women have an idea in their mind what they want their wedding to look like long before they have a boyfriend.” – Melissa [25:14]
• Pressure and Singlehood
  • Amy discusses being content but ready for love, clarifying she isn't desperate but likes to be prepared, aiming to marry in the next three years—but won’t be “crushed” if not.
  • “I’m just tired of being at home. I just want to meet someone.” – Amy [31:41]
• Dating Setup Live On-Air
  • Several men call to “pitch” themselves: from Douglas, the easygoing realist, to Carlos, the comic “Latino looking for an American wife,” and finally John.
  • The hosts vet Amy, teasing out dealbreakers and flexibility (i.e., “must love dogs and water sports”; children's names set on Sadie Bell).
  • “I’m a consultant… recruiting/human resources.” – Amy [28:29]
  • “I would love to have twins: Macon and Mason. Girls would be McCullough, Sadie Bell.” – Amy [36:48]
  • “You don’t sound so crazy to me at all… you just sound very, very honest.” – Burt [32:01]
• Show’s Takeaway
  • Amy’s openness is admired but good-naturedly ribbed, with the hosts reflecting on societal expectations around women’s “marriage timeline” honesty.

3. First Date Fridays: Janice’s Bold Blind Date Adventure

[39:19–59:18]

Part 1: The Setup

• Janice, 24, is set up for a blind date (by her stepmom) with a 48-year-old man. She flies to Jacksonville, is picked up by the date (a pilot), then flown to Miami for the weekend.
• Discussion covers parental approval (dad opposes), age-gap relationships, and whether her stepmother’s encouragement is motivated by the man’s status/money.
• “I’ve dated older men before too though.” – Janice [45:15]
• “A 49-year-old man dating a 17-year-old girl—pedophile.” – Burt [45:39]
• Janice says her main motivation is finding stability and someone ready to settle down—as younger men have disappointed her.
• The hosts express concern about safety and vulnerability, especially with Janice’s 6-year-old daughter in mind.

Part 2: The Aftermath

[52:14–59:18]

• Janice returns and recaps her weekend: The date was "cute" in person, but almost immediately upon arriving, he revealed a box of condoms and made persistent advances.
  • “We were unpacking our bags and he pulls out a box of condoms and says, see, look, I came prepared…” – Janice [53:38]
• She spent the weekend fending him off, frustrated by his lack of subtlety.
• Despite sharing the same hotel bed (clothed), she did not feel unsafe but says she would never see him again.
• Her stepmom apologized; Janice reflects she should have gotten her own room and car “next time.”
  • “I was definitely glad to be home yesterday… But it was an okay time. I had a good experience.” – Janice [54:53]
• The hosts conclude with a reminder that grand gestures (especially those involving private jets and hotel rooms) can come with expectations.
• “Guess what, Janice, they’re gonna expect the same thing this 48-year-old expected.” – Melissa [58:09]

Notable Quotes & Moments (with Timestamps)

• On romantic gestures:
  “This is the stuff that movies are made of.” – Jeff [10:46] “But every now and then, Stacy, you'll get in that hole—tell me what you love about me. List will tap at about 4. This guy had three dozen reasons on a first date.” – Burt [03:10]
• On love and planning:
  “You don't sound so crazy to me at all. You just sound very, very honest.” – Burt [32:01]
• On age-gap dating:
  “If you're a 41-year-old guy dating a 17-year-old, you're all about playing games.” – Jeff [46:25]
• On the perils of big romantic moves:
  “If he had paced himself a little more, he could have gotten it, but because he, you know, first thing he unpacks out of his, you know, carry on is the box. Slow down, chief.” – Jeff [60:01]
• On wedding pre-planning:
  “What is the difference between most women and Amy?” – Melissa [24:17] “Most guys live with the notion that women are ready to marry at all times. We just don't want to hear about it.” – Burt [27:52]

Tone & Language

• Conversational, candid, sometimes irreverent—hosts frequently tease one another, poke fun at societal norms, and exhibit skepticism toward overly saccharine, impractical, or "soap opera" romance.
• Listeners are invited into the candor, with call-in segments providing authenticity and humor.

Useful Timestamps for Navigation

• [01:10–19:57] – Romantic story competition and Jeff's "movie-worthy" narrative
• [20:33–38:00] – Amy and the dream wedding with no groom; live dating setup
• [39:19–59:18] – Janice’s blind date saga, from plan to uncomfortable reality

Final Takeaways

The Bert Show episode is a fun, sometimes poignant glimpse into the modern romantic psyche—showcasing the tension between fantasy and reality, planning and spontaneity, and the ever-conflicted desires for true love, security, and adventure. The hosts’ willingness to challenge listeners and each other keeps the tone lively and authentic, making (sometimes cringe-worthy) real-life stories both accessible and entertaining.

Best For: Anyone who loves real talk about relationships, enjoys hearing everyday people’s wild and heartfelt stories, or just needs a dose of morning laughter with a side of relatability.