Podcast Summary: The Bert Show

Episode Title: Vault: She’s In Her 20s And NEVER Had Been On A Date!
Release Date: January 14, 2026
Host: The Bert Show Cast (Pionaire Podcasting)

Episode Overview

This episode revisits the ongoing story of Dana, a 27-year-old woman who, until recently, had never been on a date. The episode explores her whirlwind entry into dating, beginning with her parents setting her up with a 58-year-old man, Carl, and the challenges she's faced as their relationship quickly accelerates. The show features reactions from the cast and callers as Dana navigates intense emotions, second thoughts, and the pressures of her first romantic relationship—all while grappling with issues of age difference, inexperience, and personal growth.

Key Discussion Points & Insights

1. Dana’s Unique Situation and Recap

• [01:20] Host summarizes Dana’s journey:
  • At 27, she’d never been out on a date.
  • Her parents set her up with Carl (58 years old).
  • Their relationship progressed rapidly—talks of moving in and having children.
  • On a vacation with Carl, Dana meets a younger, attractive man by the pool (her own age) and is struck by the attention.

“I can’t believe I’m talking to this cute guy, because…this wouldn’t have happened seven months ago.” — Dana [02:59]

2. Reactions from the Show and Predictions

• After replaying their last call with Dana, the hosts and callers make bold predictions about her next steps:
  • Will Dana date the young guy or stay with Carl?
  • Some joke about her marrying Carl or even adopting children with him.
  • Others wonder if she wimped out and stayed with Carl out of comfort and nurture.

“She either married to the old guy or she completely dumped him and started seeing the younger guy.” — Host [04:07]

• The cast jokes light-heartedly about possible scenarios, poking fun at Carl’s age and eccentric habits, insinuating wild or unexpected events on their Bahamas trip.

“I think that their last day down in the Bahamas, she probably walked in and caught Matlock giving himself a vegetable enema…” — Caller [05:30]

3. Dana's Big Decision

• [06:01] Dana rejoins the show for an update:
  • She tells Carl about meeting the young man but, due to Carl’s sad reaction, decides not to pursue the new connection.
  • Dana admits her decision was motivated by not wanting to hurt or lose Carl.
  • She reflects honestly about some regret and lingering curiosity about what she might have missed with the younger man.

“I kind of have been thinking about it…just wondering if I made the right decision, if I should have gone out with him…” — Dana [07:26]

4. Feeling Bored—Normal or a Red Flag?

• Dana reveals she's started feeling bored with Carl.
  • She expresses a desire to spend July 4th with her girlfriends instead of going on a trip with him, craving more space.

“I kind of want to hang out with my girlfriends…but I already talked to him about going to New York…I'm just sort of thinking right now if I should stay home with my girlfriends or go with him.” — Dana [08:20]

• The hosts discuss the honeymoon phase and whether Dana’s boredom is a warning sign or just part of normal relationship progression.

“It’s so hard because you have no experience to fall back on…this guy still bores me to tears, you know?” — Host [11:54]

5. Callers Weigh In: The Age Gap vs. Inexperience

• Some callers urge Dana to date around before settling, highlighting the potential pitfalls of letting her first-ever romantic partner become her life partner.

“Anybody who went out on their first date, one date, and then decided that's the person they want to spend the rest of their life with is wrong. Like, don't do that…” — Caller [15:03]

• Others emphasize that the core issue isn’t Carl’s age, but Dana’s lack of dating experience.

“Can we please take the age out of this and remember that Dana is dating her first person ever…even if she was 21 and the guy was 22…” — Caller [14:13]

6. Dana’s Uncertainty and Growth

• Despite all the input, Dana is unsettled:
  • She likes Carl but isn’t ready to end things just because she’s bored.
  • She’s unsure about her plans for July 4th, torn between Carl and her friends.

“I still really like Carl... I’m not ready to say, because I’m feeling a little bit bored, that I want this to stop.” — Dana [15:38]

• The cast notes a change in Dana’s demeanor: more mature, less giddy than before—showing real growth through her experiences.

“I thought when we've…talked to her about Carl, she’s been like…giggly and giddy, and this time she’s like, ‘Yeah, I’m not so sure.’” — Caller [16:29]

Notable Quotes & Memorable Moments

• On sudden attention:
  “I can’t believe I’m talking to this cute guy…if this would have happened, like, seven months ago…I just felt like this wouldn’t have happened.” — Dana [02:59]

• On moving too fast:
  “A couple of weeks ago, you were talking about marrying this guy and having kids with him, and now you’re saying you’re kind of bored…” — Host [10:07]

• On her friends’ advice:
  “They still don’t like me going out with him…sometimes I don’t talk to them about it because I know what they’re going to say…” — Dana [09:33]

• On relationship firsts:
  “Anybody who…decided that’s the person they want to spend the rest of their life with is wrong. Like, don’t do that. That’s a bad idea.” — Caller [15:03]

Key Timestamps

• [01:20] — Recap of Dana’s journey: first relationship, rapid progression.
• [02:11] — Dana recounts meeting the younger man in the Bahamas.
• [03:12] — Dana’s reflections on her unexpected romantic predicament.
• [04:07] — Cast predictions about her future.
• [05:30] — Joking predictions about wild scenarios.
• [06:01] — Dana’s major update: she stayed with Carl.
• [07:26] — Dana admits lingering thoughts about the young man.
• [08:13] — Dana’s growing boredom with the relationship.
• [10:07] — Discussion of moving from honeymoon phase to reality.
• [14:13] — Callers debate the real issue: age gap or inexperience?
• [16:29] — Cast notices Dana’s matured voice and outlook.

Takeaways

• Dana’s story illustrates the complications that come with a late start in dating: accelerated emotions, uncertainty, and the pressure of first experiences.
• Despite advice and differing opinions, Dana remains indecisive about her next steps, embodying the awkward but authentic confusion of a first relationship.
• Both the hosts and callers recognize that her situation is less about the age difference and more about her need to explore and define her own romantic preferences—before making major commitments.

Next Update: The cast promises to check in with Dana after July 4th to see what she ultimately decided and how she's feeling about her relationship moving forward.