The Bert Show: Vault – Full Blind Date Janice

Original Air Date: November 3, 2025
Podcast Host: Pionaire Podcasting
Episode Focus: Janice's First Date Friday – The Full Blind Date Recap

Episode Overview

In this episode of The Bert Show, the team revisits one of their popular "First Date Friday" segments featuring Janice, a 24-year-old listener whose stepmom set her up on a blind date with a 48-year-old pilot from Virginia. The episode is presented in two parts: the Friday morning call before Janice embarks on her date, followed by a Monday morning follow-up where Janice recounts her weekend experience in Florida.

Key Discussion Points and Insights

1. Setting the Stage: Janice's Blind Date Setup

[00:47 – 05:26]

• The Bert Show introduces Janice and explains "First Date Friday."
• Janice describes how her stepmother (not biological mother) set her up with a 48-year-old man, a friend of the stepmom's boyfriend.
• Janice is flying to Jacksonville, FL, to be picked up by her date who will then fly her on his private plane to Miami for the weekend.

Quote – [02:32]
Janice: "My dad and my mom are divorced and my dad is totally 100% against this, but my mom is dating a man... This is a friend of his... I'm actually flying... to Jacksonville and he's going to pick me up... and fly me down on his plane to Miami. He's a pilot... He is 48, I am 24, and we've been talking on the phone for just over a week now..."

Concerns Raised by the Hosts:

• Safety and parental responsibility (especially flying with a stranger met only over the phone).
• The influence of the man’s wealth and whether it affects the stepmom's judgment.
• The age difference & Janice's dating history with older men; Janice states she’s comfortable with large age gaps.

Quote – [05:45]
Host: "When you've got that kind of cash and that kind of security for your daughter, then all of a sudden that guy becomes a lot better catch..."

2. Delving Into Janice's Past & Motivations

[06:01 – 12:14]

• Janice reveals a pattern of dating much older men; describes previous relationships, including dating a man in his 40s while still a teenager.
• The hosts react with questions and concern regarding the age differences and reasons for her preferences.
• Janice lost significant weight recently and says she's been dating more but feels let down by men her own age.

Quote – [06:15]
Janice: "I dated when I was 17, a man who just turned 49 last month... for three years I dated a man who just turned 40 in December..."

• Janice shares details of her own single-motherhood at 24, explaining how the father of her child (a 29-year-old when she was 17) left after finding out she was pregnant.

Quote – [11:48]
Janice: "I told [my daughter's father] I was pregnant. And he changed his cell phone number, disconnected his pager, and moved... He's never seen her. And I haven't talked to him since..."

3. Friday: The Team Gives Janice Final Advice

[12:14 – 12:51]

• The hosts urge Janice to remember her responsibilities as a mom, echoing safety and emotional wellbeing.
• Janice says she has friends checking in on her throughout the weekend.

Quote – [12:20]
Host: "You've got a daughter to protect here also... when you put yourself in a situation like this where you're really vulnerable... you're putting your daughter in that situation too, you know?"

4. Monday Recap: How the Weekend Actually Went

[13:01 – 19:32]

• Janice returns and describes her Florida weekend as "definitely a learning experience."
• She says the man was physically attractive, but as soon as they arrived at the hotel, he immediately began making sexual advances.
• He explicitly showed Janice a box of condoms within minutes of arriving.

Quote – [14:26]
Janice: "He pulls out a box of condoms and says, 'See, look, I came prepared.' [...] He bought a 12-pack, and needless to say, he didn't need to even bring any..."

• Janice reports spending the weekend "trying to get him off me," reinforcing she did not feel unsafe but was constantly warding off his advances.

Quote – [14:48]
Janice: "I was like, oh my gosh. And I mean, I was really stunned. [...] I told him that about 20 times and we actually had an okay time."

• The hosts affirm their earlier predictions that a man investing so much in a first date would likely expect intimacy.

Quote – [15:13]
Host: "A 48-year-old man is not going to, well, beat around the bush. He's going to want to... I mean, I'm not surprised."

• Janice slept in the same bed but stayed clothed, "counting down the minutes" until departure.

• She reports her stepmom apologized and realized she didn't know this man as well as she thought.

Quote – [16:25]
Janice: "[My stepmom] apologized, 'I'm so sorry. [...] I guess you never really know anyone until you're actually in a personal setting with him.'"

5. Reflections and Takeaways

[18:47 – 19:32]

• Janice says if she were to do it again, she’d get her own room and car.
• She received feedback and messages from listeners, mostly showing concern.

Quote – [19:07]
Janice: "I would have made sure I had my own room and my own rental car... we could have had a good time if we were just separated a little bit more..."

6. The Team's Final Thoughts

[20:15 – 21:13]

• After Janice hangs up, the team debates whether Janice downplayed what happened, with some speculating more may have occurred.
• Light-hearted banter and teasing ensue, reiterating the unpredictability of dating and the lessons to be learned.

Quote – [21:01]
Host: "If he just is cool about it in the beginning, he probably has a fantastic time over the weekend..."

Memorable Quotes & Moments

• [06:07] Janice: “Significantly older? 3.”
• [14:26] Janice: “He pulls out a box of condoms and says, 'See, look, I came prepared.'”
• [15:59] Janice: “No, not a chance.” (On going out with him again)
• [17:20] Janice: “Yes, but I wore clothes.” (On sharing a bed)
• [19:07] Janice: “I would have made sure I had my own room and my own rental car and that's about it.”
• [16:25] Janice: “[Stepmom] apologized. ‘I'm so sorry. I thought he was such a nice guy…’”
• [08:22] Host: "From a guy's perspective… this man is expecting something physical over the weekend."
• [10:22] Host: “Are you starting to feel like you're getting a little too old not to have a father figure for your child?”

Timestamps for Key Segments

• [00:47] – Introduction of Janice and the blind date premise
• [02:32] – Janice gives background and details of her setup
• [06:07 – 07:11] – Janice reveals history with much older men
• [11:48] – Janice explains her daughter's paternity history
• [13:41] – Monday follow-up: Janice's trip to Florida
• [14:26] – Condom confrontation in the hotel
• [16:25] – Stepmom's reaction to the failed date
• [17:20] – Janice confirms she stayed clothed and brushed off advances
• [19:07] – Janice shares what she'd do differently
• [20:15 – 21:13] – Team’s closing remarks and speculation

Summary Takeaways

• Janice’s blind date with a significantly older man, orchestrated by her stepmom, turned into an uncomfortable experience marred by unwanted advances and a lack of anticipated romance.
• The Bert Show team highlighted the pitfalls and concerns of rapid, high-stakes dating situations, particularly regarding safety, age disparity, and expectations.
• Janice, while reflecting on her choices, intends to adjust her approach to future dates by ensuring greater autonomy and boundaries.
• The episode underscores the unpredictable realities of modern dating—and delivers plenty of candor, humor, and insightful commentary from both Janice and the cast.