The Bert Show: "Vault: He’s Nervous About His First Date In 15 Years"
Episode Date: December 22, 2025
Main Cast: Bert, Kristin, Abby, Cassie, Tommy, & The Bert Show Cast
Episode Overview
In this heartfelt and humorous episode, the team follows up with Charlie, a recently divorced father who is going on his first date in 15 years. The segment explores Charlie's nerves and anticipation, the advice he receives from both the hosts and listeners, and a detailed recap of his experience. The conversation provides warmth, comic relief, and genuine support as Charlie navigates the modern dating world after a long hiatus.
Key Discussion Points & Insights
1. Charlie’s Story and Pre-Date Nerves
[01:26-03:41]
- Charlie, 42, recently finalized his divorce after a 12-year marriage and is a father of two.
- A coworker set him up with a woman in her mid-30s.
- He admits feeling "bunched up" and anxious at the prospect of dating again.
- Charlie: "I feel a little, you know, bunched up about it." [01:29]
- The Bert Show team and listeners offer advice:
- T.C.: "Just relax and be yourself... Don't dwell on your ex wife." [02:17]
- Nora: "Let this person know how much a part of your life your kids really are... have that out there from the beginning." [02:45]
- Charlie is reassured about not talking excessively about his ex and instead focusing on who he is now and being upfront about his kids.
2. Lead-Up to the Date: Emotions and Preparation
[03:01-05:00]
- Charlie thanks everyone for their practical advice, particularly about being a gentleman and not forcing things.
- He created a checklist (don’t dwell on ex, bring flowers, be attentive).
- Charlie: "It was kind of nice to have like a checklist in front of me because it helped me focus... and not be so nervous." [03:41]
- He felt nervous going to another woman’s apartment for the first time and noted the unfamiliarity of it all.
3. Date Recap – From Awkwardness to Connection
[05:23-09:17]
- Brought flowers; the woman invited him into her apartment briefly, which he found both "strange" and "exciting."
- Charlie: "Just being in another woman's apartment... was really kind of unnerving. At first I thought it was exciting, but... I hope nothing happens right now, because I was really. I was not all, you know..." [05:56]
- They went to her favorite restaurant, where Charlie focused on being attentive and opening doors.
- He candidly admits that moments made him reflect on his marriage:
- "Maybe if I'm fitting this way all the time with my wife, maybe we wouldn't have those problems." [07:23]
- Discussed his kids openly during dinner; the date was supportive and agreed not to meet his children immediately.
- Charlie: "I think it's better that I don't meet them right away, that you don't have to introduce me to them..." [08:30]
- Charlie describes the evening as sweet:
- "It felt like doing it all over again, which was really... just really, really nice." [09:02]
4. Physical Chemistry and Modern Dating Pressures
[09:17-09:53]
- The team probes about physical attraction. Charlie confirms there was mutual interest.
- Charlie: "Yeah, there really was for me... I think she sensed it too." [09:28]
- A comic interlude: a host quips about “sealing the deal” on second dates and modern dating culture.
- G: "Nowadays, on the second date's when you got to seal the deal. You know what I mean?" [09:47]
- The team jests about dating norms and overshares, adding levity.
5. The End of the Night & What’s Next
[10:09-11:24]
- Post-dinner, she invites him up for a drink, but Charlie keeps the night short for his kids’ sake.
- The evening ends with a kiss on the cheek and plans for another date:
- Charlie: "I gave her a nice kiss on the cheek, asked her if she wanted to go out again, and she said she would." [10:55]
- Hosts celebrate that everything went smoothly.
- "Most Bert Show stories don't end up on such a great note like this." [11:38]
6. Reflections and Lighthearted Closer
[11:21-12:09]
- Charlie expresses gratitude for the advice and admits the experience was invaluable.
- Charlie: “Thank you. Thanks for all the help.” [12:08]
- The hosts warn him to “not jack it up” and suggest they're "waiting for the other foot to drop" (jokingly).
- Playful speculation about disaster scenarios (falling for her sister, secret sexuality) provides a comedic end.
Notable Quotes
- Charlie: "I just feel a little, you know, bunched up about it." [01:29]
- T.C. (listener): “Just relax and be yourself. Don’t dwell on your ex wife.” [02:17]
- Charlie: "It was kind of nice to have like a checklist in front of me because it helped me focus... and not be so nervous about stuff." [03:41]
- Charlie: "Just being in another woman's apartment... was really kind of unnerving... it was exciting, but... I was not all, you know..." [05:56]
- Charlie: “It felt like doing it all over again, which was really, really nice.” [09:02]
- G (host): "Nowadays, on the second date's when you got to seal the deal." [09:47]
- Charlie: “I gave her a nice kiss on the cheek, asked her if she wanted to go out again, and she said she would.” [10:55]
- C (host): “Most Bert Show stories don't end up on such a great note like this.” [11:38]
Important Segment Timestamps
- [01:26] — Charlie introduces himself and his nerves about dating post-divorce
- [02:17] — Listener T.C.’s core advice
- [03:41] — Charlie talks about preparing for the date with a checklist
- [05:23] — The initial moments in his date’s apartment
- [07:23] — Charlie reflects on lessons from his marriage
- [08:30] — Conversation about introducing dates to kids
- [09:28] — Addressing mutual attraction on the date
- [10:55] — Kiss on the cheek and confirmation of a second date
- [11:38] — Hosts’ celebratory reactions and comic relief
Episode Tone and Takeaways
- Genuine, supportive, lighthearted, and humorous—the cast creates a warm environment while offering actionable advice.
- The episode is a relatable and heartfelt look at vulnerability, growth, and new beginnings after life-changing events.
- Charlie’s journey serves as both encouragement and reassurance to listeners facing similar circumstances, with the Bert Show’s trademark mix of empathy and wit.