Vault: 2nd Date Update - Jessica & Ken

Summary

The Bert Show – Vault: 2nd Date Update - Jessica & Ken

Date: October 28, 2025
Podcast Host: The Bert Show Cast
Featured Speakers: Ryan, Jessica, Ken, and listeners

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Episode Overview

This episode is a classic installment from The Bert Show's beloved "2nd Date Update" series, where awkward dating situations get unravelled live on air. Today’s scenario dives into an epic misunderstanding between Jessica, who believes she went on a promising first date with Ken, and Ken, who is adamant that their meeting was strictly business—and that he’s married. The segment showcases confusion, miscommunication, and the comedic fallout when expectations collide.

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Key Discussion Points & Insights

1. The Setup: Jessica Seeks Answers

Timestamp: [01:59]

• Jessica reaches out to The Bert Show curious about why Ken hasn't called her back after what she felt was a great date involving a movie and drinks.
• Ryan sets the scene for the listeners and connects both Jessica and Ken live on air:

  "We've got a bit of a question for you because Jessica's a little miffed... she can't figure out why you haven't called her back for a second date." — Ryan [02:23]

2. The Confusion: Was It a Date?

Timestamp: [02:38]

• Ken responds with surprise, categorically stating:

  "Oh, my gosh. We didn't go on a date. What? You know we didn't go on a date." — Ken [02:38]

• Ken reveals they first met at a party where his wife was present, and affirms his marital status.
• The outing in question (movie and drinks) was with Ken’s 13-year-old daughter and her friends, not a one-on-one date.

3. Differing Impressions: Flirtation & Intent

Timestamps: [03:04] – [04:44]

• Jessica maintains that Ken was friendly and offered to pick her up, interpreting this as romantic interest.
• Ken insists all his actions were related to a business connection—Jessica is a networking coach, Ken works in sales, and he sought professional advice.
• Ken:

  "She coaches people on how to network. I work in sales... My wife was standing right there with me..." — Ken [03:04]

• Jessica claims Ken was flirting with her at the party, to which Ken audibly groans.

4. The Movie Night: Mixed Signals

Timestamps: [04:18] – [05:01]

• Jessica feels picked up, paid for, and accompanied at the movie—classic date signals.
• Ken reiterates that the movie was a family event and the follow-up drinks were at a mall food court with kids present.
• When Jessica wasn’t surprised by the presence of Ken’s daughter, she rationalized:

  "I thought, you know, sometimes when you go on a date with someone, they want you to meet their kids." — Jessica [04:53]

5. Fallout: Messages and Misunderstandings

Timestamps: [05:01] – [05:49]

• Ken’s wife heard multiple voicemails from Jessica, escalating the awkwardness.
• Jessica comments that Ken was physically close during the movie; Ken attributes this to his daughter being frightened during the film.

  "My daughter was afraid of the movie. She was practically in my lap." — Ken [05:18]

6. Resolution: Realization & Embarrassment

Timestamps: [05:53] – [06:15]

• Ryan and the hosts highlight the breakdown in communication, with Jessica finally conceding,

  "I mean, obviously, we got our signals crossed." — Jessica [05:35]

• Both parties hang up, with an air of resignation and embarrassment.

7. Listener and Host Reactions

Timestamps: [06:18] – [07:14]

• Listeners and hosts weigh in, some defending Ken and others expressing second-hand embarrassment for Jessica.
• Notable listener quote:

  "She played herself with a capital P. How in the world do you think...he don’t want you? She needs some friends." — Cicely [06:34]

• Ryan reflects on the power of wishful thinking:

  "I think maybe sometimes you just see and hear things that you want to see and you want to hear." — Ryan [07:03]

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Notable Quotes & Memorable Moments

• "We didn't go on a date. What? You know we didn't go on a date." — Ken [02:38]
• "My wife was at the party also." — Ken [02:51]
• "He was also sitting very close to me in the movie." — Jessica [05:11]
• "My daughter was afraid of the movie. She was practically in my lap." — Ken [05:18]
• "Can I go?" — Jessica, realizing the situation [06:11]
• "She played herself with a capital P." — Listener Cicely [06:34]
• "This woman smoked too much crack." — Ken, in post-call commentary [07:17]

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Important Timestamps

• [01:59] – Segment begins, Jessica explains her confusion to the hosts
• [02:38] – Ken’s surprise and declaration that it was not a date
• [03:04] – Ken explains the business context of their interactions
• [04:18] – Disagreement about the signals and invitations
• [05:11] – Jessica discusses proximity at the movie
• [05:35] – Jessica acknowledges crossed signals
• [06:34] – Listener Cicely’s commentary on Jessica’s misreading
• [07:03] – Ryan’s reflection on human perception and misunderstanding

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Tone & Style

• Authentic, lighthearted, and filled with genuine moments of cringe and empathy.
• The hosts maintain a friendly, humorous, and occasionally teasing rapport with both participants.
• Listener call-ins add a candid, unfiltered edge—ranging from supportive to brutally honest.

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Conclusion

This 2nd Date Update segment is a classic case of mixed signals, where one person’s networking opportunity is another’s would-be romance. The episode captures the best of The Bert Show’s charm: humorous, real, and occasionally mortifying dating moments dissected for all to learn (and laugh) from. The responses from both the studio cast and audience reveal how varied perceptions can be—and how sometimes, you just need a radio show to set the record straight.

Transcript

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[Ryan]

The Bird show this poor woman took so much heat because she had absolutely no idea what was going on. She thought she was on a date. Problem is, the guy that she was with didn't think it was a date at all. Hi Ken yes, hi. This is The Birch show at Q100 calling you. We're on the air right now. How you doing, man?

[Jessica]

Good.

[Ken]

How are you?

[Ryan]

Hey, dude, we have Jessica on the phone with us. Jessica, you want to say hey?

[Jessica]

Hi, Ken.

[Ken]

Hi. Hi, Jess.

[Ryan]

Hey, Ken, we've got a bit of a question for you because Jessica's a little miffed. You know, she was telling us that she went out with you. What was it, last week, and she had a really great time on your date, enjoyed the movie with you, enjoyed going out and getting a little drinky drink afterwards. Well, now she can't figure out why you haven't called her back for a second date.

[Ken]

Oh, my gosh. We didn't go on a date. What? You know we didn't go on a date.

[Ryan]

How can there be confusion about that?

[Caller/Listener]

Yeah, you guys met at a party. She asked you.

[Ken]

We met at a party with my. My wife was at the party also.

[Ryan]

Oh, okay.

[Ken]

Yeah.

[Caller/Listener]

Did you go to a movie with her?

[Ken]

Yeah, with my. My daughter and her two friends.

[Ryan]

This changes things.

[Jessica]

Still a date.

[Ken]

It wasn't a date. She coaches people on how to network. I work in sales.

[Tony]

Okay.

[Ken]

Basically, we met at the party. My wife was at the party, and she was telling me all these seminars that she does. And I was like, well, this sounds great. It sounds like something I could use. She's telling me how she charges thousands and thousands of dollars to do these seminars. So I'm like, well, you know, looking into it and talking to her. My wife was standing right there with me. She says, listen, I would love to just get together and just, you know, just show you some different things that, you know, we could do that you could probably use. No charge. So me being interested, of course. Just what I do. I said, listen, sounds great. You know, I was talking to my wife about going to the movies. She said, listen, why don't I come along? She invited herself along to go see Panic Room. So my wife was there. I was like, well, that sounds fine. Let's do that. You know, my daughter will be there. Two friends will come. We ended up going to the movie, watching the movie. After the movie, we. We went to, like, the. The mall. My. My kid and her two friends were actually going shopping around. We went to a little place in the food court there, had a couple of drinks, and we talked about it.

[Ryan]

Oh, this changed.

[Jessica]

He goes to a movie with a woman he's not interested in.

[Ryan]

Well, wait a second now, Jessica. You knew he was new.

[Jessica]

Why did you invite me to the movie?

[Ken]

Because I thought we were going to talk. Because we talked about what you did, and it was helping me. And that's the whole reason why I even paid for you. Because it was just a common courtesy of you just telling me everything about what you do. My daughter and her two friends were there.

[Ryan]

How old are your Is your daughter?

[Ken]

My daughter's 13 years old.

[Jessica]

And he offered to pick me up?

[Ken]

Yeah, of course I did. I figured that you were cutting me this great deal. Why shouldn't I come and pick you up with my daughter and two and her friends?

[Jeff Bridges]

You obviously knew he was married.

[Jessica]

Yeah, but he was still flirting with me at the party.

[Ken]

Oh, my gosh.

[Ryan]

And when he showed, Was it a surprise to you when he showed up with his two kids?

[Jessica]

No. I thought, you know, sometimes when you go on a date with someone, they want you to meet their kids.

[Ken]

Obviously there's something wrong with this woman. Then she listens to this. Then she leaves me two messages. Why haven't you called me? My wife heard the messages. She knows everything about it.

[Jessica]

He was also sitting very close to me in the movie.

[Narrator/Host]

In the next seat.

[Ken]

My daughter was afraid of the movie. She was practically in my lap.

[Jessica]

Yeah, and so was I. Oh, my gosh.

[Ken]

You are crazy.

[Ryan]

Jessica, can you sort of see how this could be seen as kind of more of as a business thing than our actual date?

[Ken]

Yeah.

[Jessica]

I mean, obviously, we got our signals crossed.

[Ken]

Well, where did you go wrong in that? Like when? When I introduced you to my wife or to my daughter?

[Caller/Listener]

Or did you get any signals like this, Ken, while you were on the date that she might be thinking that more's going on?

[Ken]

I was not. I personally wasn't even in this range of thinking.

[Ryan]

Hey, Jessica, did it ever dawn on you that he was only talking about work and nothing else going really on in his life?

[Jessica]

Well, I think he was doing that because, you know, he was nervous. He's probably anxious.

[Ken]

He's been married for a while.

[Jessica]

He was on a date.

[Ken]

Oh, wow.

[Jeff Bridges]

Talk about miscommunication.

[Jessica]

Yeah. Yeah. Can I go?

[Ryan]

Sure.

[Narrator/Host]

Okay.

[Ryan]

Sure.

[Jessica]

Thank you. All right.

[Ryan]

Bye, both of you guys.

[Jessica]

Thanks.

[Ryan]

Oh, my God.

[Caller/Listener]

That's my favorite one ever, I think.

[Ryan]

Are you kidding me? Good morning, Q100.

[Ken]

Hi.

[Tony]

Hi.

[Jessica]

Jessica is just crazy.

[Ken]

I don't know how she misunderstood it.

[Jessica]

Y' all need to keep this for the file.

[Ryan]

Thank you.

[Jessica]

All right. Bye. Bye.

[Ryan]

Morning, Q100.

[Jessica]

Hello. Hello. My name's Cicely, and I have to say, she should have just hung up the phone because I'm embarrassed for her. I am embarrassed for this woman. She played herself with a capital P. How in the world do you think. Come on, don't play yourself. If I was her friend, I'm like, listen, he don't want you. She needs some friends. I mean, she's probably sitting at home alone. She's lonely, you know? So embarrassing.

[Ryan]

I think maybe sometimes you just see and hear things that you want to see and you want to hear. And you don't take any kind of common sense in a play, you know, I think.

[Jessica]

I think you're right.

[Ryan]

See you, Sicily. Bye now.

[Jessica]

Okay. Bye.

[Ken]

Bye.

[Ryan]

Hi, Q100.

[Ken]

This woman smoked too much crack.

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