Vault: He's Looking For A Date To Join Him On A Cruise

Summary

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Podcast Summary: The Bert Show

Episode: Vault: He’s Looking For A Date To Join Him On A Cruise
Date: March 11, 2026

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Overview

In this engaging and offbeat episode, the Bert Show crew welcomes Richard, who finds himself with a spare ticket—and no companion—for an imminent Caribbean cruise. After being ditched by his recent date but not the vacation plan, Richard enlists the show’s help to find a last-minute travel companion. The episode blends humor, real talk, and a playful yet practical vetting process as The Bert Show community considers joining this unexpected adventure.

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Key Discussion Points & Insights

1. Richard’s Unusual Dilemma (00:53 – 02:22)

• Background: Richard recounts meeting "Jill" a year ago, reuniting, dating for about six weeks, then planning a New Year’s cruise together.
• The Twist: Jill breaks up with him 12 days before departure but still wants to go on the cruise.
• Richard’s Predicament: Scrambles to find a new travel companion, encouraged by his friend Pam to turn to The Bert Show.

Quote: "So she was breaking up with you, but she still wanted to go to the Caribbean.” — Host (02:04)

2. The Cruise Offer Details (02:24 – 03:40)

• Trip Dates & Logistics:
  • Available from the 29th to the 3rd, cruise out of Tampa, FL, to Cozumel and Grand Cayman.
  • Companion must provide their own transportation to Tampa (estimated $400-500 for a flight).
  • Must have valid passport.
• Accommodations:
  • Shared cruise cabin with two beds (configurable), “You can see as much or as little of me as you need throughout the cruise.” (04:10)
• Ideal Companion:
  • Fun, adventurous woman, late 20s to early 30s, open-minded enough to travel with a stranger.

Quote: “That’s such an odd request—to say, ‘Hey, I don’t know you, but let’s go on a cruise.’” — Richard (03:51)

3. Safety, Intentions, and Trust (03:46 – 05:03)

• The show candidly acknowledges safety concerns for women sharing a room with a man they don’t know.
• Richard offers to provide references, vouches for his character, and the show tries to help listeners get a read on him by asking the “first date questions.”

Quote: “Why should a woman feel safe with you on a boat for five days?...That needs to be addressed.” — Show Host (04:31)

4. Getting to Know Richard (05:08 – 07:44)

• Profession: Software engineer in Atlanta.
• Background: From Oklahoma, family-oriented, went to Oklahoma State.
• Personality & Interests: Adventurous, enjoys scuba diving, social gatherings, dining out, and travel experiences (e.g., Europe, skiing, London, Paris).
• Past Relationships: Never married, longest relationship lasted two years.
• Fun Questions: Age 37, Libra, likes emotional movies (“I actually don’t remember what the movie was, but I do like emotional movies.” — Richard, 07:37)
• Excursions: Booked snorkeling with stingrays in Grand Cayman, dolphin experience in Cozumel.

5. Live References and Callers (08:05 – 10:34)

• Coworker Endorsement: “He’s a great guy, good catch for anyone.” — Shel, coworker (08:18)
• First Applicant: Emily, 37, blonde, fun, loves cruising, already has time off—potential match!
• Plans set for Richard to spend the next 24 hours meeting or talking with interested listeners to select a companion.

6. The Selection Process (10:34 – 11:18)

• Contact Information:
  • Email and photo exchange set up through the station’s website.
  • Phone line open for applicants.
• Urgent Timeline:
  • Richard has 24 hours to meet or chat with applicants and make his choice.
  • “He’s got 24 hours to choose one of you to go on this vacation with him down to the Caribbean.” (11:50)

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Notable Quotes & Memorable Moments

• On the whole idea:
  • "For the first 24 hours, this is going to be weird." — Host (03:55)
• On room arrangements:
  • “You can see as much or as little of me as you need throughout the cruise.” — Richard (04:10)
• On personal background:
  • “Yeah, I’m a software engineer for a company here in Atlanta.” — Richard (05:10)
  • “I do. Hi, Mom.” — Richard, about his mother (05:20)
• When asked about being over his ex:
  • “Yeah.” — Richard (06:32)
• When pressed for details:
  • “Feel like we’re pulling teeth here.” — Host (07:53)
• Emily’s self-description:
  • “...people say I’m attractive. I think I’m somewhat attractive. And I think it’s more my personality that is important, very fun, and just like to try new things.” — Emily (09:22)
• On process logistics:
  • "The turnaround on this is very, very quick. You gotta be gone on the 29th." — Host (11:00)

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Timestamps for Important Segments

• 00:53 – 02:22: Richard’s situation and how he ended up on the show
• 03:24 – 04:10: Logistical and safety concerns, criteria for applicants
• 05:08 – 07:44: Rapid-fire personal questions to Richard
• 08:05 – 08:35: Shel, coworker and reference, calls in
• 08:45 – 09:43: Emily, first interested listener, applies on-air
• 10:34 – 11:18: Contact details and next steps for applicants

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Conclusion

The episode captures The Bert Show’s signature blend of real-life drama, humor, and interactive community spirit as listeners are invited to join Richard’s last-minute search for a cruise companion. The segment is fast-paced, candid, and surprisingly heartwarming—a testament to the spontaneous connections and quirky problems the show loves to showcase.

Endnote:
Listeners interested in joining Richard’s adventure were directed to email and call in with photos and profiles quickly, embracing the "first-date on turbo" energy the Bert Show delivered with wit and authenticity.

Transcript

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[C]

Richard, grab a mic. How you doing here, man? Oh, I should turn your mic on. There you go. How are you?

[D]

I'm doing well, how are you?

[C]

Good. Thanks for coming in.

[D]

Thank you.

[C]

I told Richard yesterday, this is going to be a little bit like we're going to be fishing with a very short line here. There are so many variables this morning to try to find a woman to go on this trip with him. So let's take it from the very beginning here. Richard, you were just tell us the dating history, how the trip became available, where you are with it now, where she is with it at now. Just take the floor.

[D]

Okay, so I met this girl Jill about a year ago at a party I hosted and was going to ask her out, but she left before I could ask her out. Then I ran into her this year at a Halloween party, asked her out and we dated for about a month and a half. She's an amazing girl. Things went well. I thought, you know, this, who knows? But so I wanted to do something fun for New Year's and I'd asked her, hey, would you be interested in going on a cruise? She said, oh, you know, might be a little early for us to go on a cruise. But yeah, it sounds like a fun idea, no problem. A few days later, she sends me a link to a Carnival cruise and says, hey, what about this one out of Tampa? I'm going to be in Orlando. Kind of works out. All right, fine. So things were going well. Went out a few times after that, and she took me to dinner and said, hey, by the way, we need to talk. Things aren't working out. I'd like to see other people, but I still like to go on the cruise.

[C]

So she was breaking up with you, but she still wanted to go to the Caribbean.

[D]

Well, it was just an awkward situation because of the timing. It was 12 days out before the cruise departed. So, you know, who am I going to find last minute? My friends are all out of town. You know, my friend Pam said, hey, why don't you go on the Burt show?

[E]

Thanks, Pam.

[F]

Hey, Pam, what's up?

[D]

Yeah, so she said, come on the bird show.

[C]

She's like this. This story is strange enough to be on the Birch show.

[F]

This is odd.

[C]

And why don't you, let's shoot him an email. They love this. And she was right.

[E]

Well, and here you are.

[D]

Here we are. So. Yeah, so I'm looking to see if there's anybody that, you know, young, attractive girl down to earth might be interested in going on a trip, 29th through the third to Cozumel and Grand Cayman's.

[C]

Okay. So there's a bunch of details we still got to work out here. Okay. First of all, 29th through the third. Third. So you'd have to be available the 29th through the third. He doesn't have transportation to get you down to Tampa at this point. There's no flight.

[E]

Right.

[C]

So you don't have to drive yourself or fly down. So that's what round trip ticket cost you. How much?

[D]

Four or five hundred bucks at most.

[F]

Okay.

[C]

You might be able to even find something less than that.

[E]

So that's Monday through Saturday. So that's next Monday through Saturday. Correct. Just to give people, because I know everybody. If they're in their cars and don't have a calendar, then that gives.

[F]

Yeah. A week from today.

[C]

Yeah.

[F]

You have to be in Tampa.

[D]

Okay.

[C]

Okay. So you're gonna have to find your. Your own way down to Tampa. But as soon as that happens, then you're on the cruise. Tell us a little bit about who you might be looking for. Ideally.

[D]

Ideally someone late 20s, early 30s. That's fun, adventurous, likes to travel. Someone that would be fun to hang out on a cruise, even though we don't know each other. Well, it just, you know, that's such an odd request to say, hey, I don't know you, but let's go on a cruise.

[C]

I know it is.

[D]

You know, someone that's adventurous enough to do that.

[C]

I think that's the first part of it is just acknowledging, okay, for the first 24 hours, this is going to be weird.

[E]

Right. So you're sharing a cabin together.

[C]

Yeah.

[D]

There's one tow cruise, two beds that they're separate but could push together as a queen bed. If needed.

[C]

Okay. But if not, you can certainly keep them separate.

[D]

You can see as much or as little of me as you need throughout the cruise. Okay.

[C]

Is it a little itty bitty bitty room? I've been on those cruises before and I've been on a couple of them and some of them are really teeny and there are others where you could actually escape from somebody.

[D]

It was a last minute booking, so about the only thing available was a medium sized room.

[E]

So bad.

[F]

And does she need a passport?

[D]

Yes.

[F]

Okay.

[C]

Okay.

[E]

She needs a passport.

[C]

Really? Fine.

[E]

Question and let me just say, and I guess to acknowledge or to, to acknowledge the fact that why should a woman feel safe with you on a boat for five days? Because I think for women that's. I mean, absolutely.

[C]

I mean we've got to worry about that.

[E]

Sharing a room with a strange man for five days on a boat. That's a good point. That it needs to be addressed.

[C]

You got to tell us a little

[D]

bit about references if you need. No, I mean, I'm a good guy. I'm a true gentleman. I don't really know how you can back that up other than references. But Bert will vouch for me. Right.

[C]

Well, I've talked to him for like four minutes. Yeah, he seemed like a pretty decent guy. Seeing him today seems like a pretty decent.

[F]

Do you feel comfortable telling us what you do for a living?

[D]

Yeah, I'm a software engineer for a company here in Atlanta.

[F]

Where'd you grow up?

[D]

Oklahoma.

[F]

Oklahoma. Good family. You still in touch with your family?

[D]

I am flying there for Christmas.

[E]

Do you love your mama?

[D]

I do. Hi, mom.

[F]

Do you have siblings?

[D]

Yes, one sister.

[F]

I'm trying to ask all the first date questions. Where'd you go to school?

[D]

Oklahoma State.

[F]

Oklahoma State. Okay. Are you a big football fan?

[D]

Not so much.

[F]

Okay. What do you do in your spare time? You golf? You have, I mean, hobbies.

[D]

I have hobbies. I like to do adventurous things like the bird show. That's pretty high on the list.

[F]

Yeah.

[D]

I like to go scuba diving. I like flying in planes, like bike planes over Atlanta.com, that kind of thing. And just going out to eat at

[E]

restaurants, trying new things and going along those lines. Like when you usually on a cruise and you get to your port, then you have activities that you can do while you're on land. What are some of the things that you'd like to do? The excursions?

[D]

Well, I've purchased two exc. One in the Grand Cayman, which is snorkeling with the Stingray. Stingray City and then in Cozumel, they're doing the dolphin. Push, pull, swim. So the dolphin gets to pull you around.

[C]

Yeah.

[E]

Very nice.

[C]

On any given weekend, what do you generally do? I'm just trying to give them a better sense of who they'll be hanging out with.

[D]

Okay. Hang out with friends. A lot of parties at my house or at other people's houses. I live in midtown, so it's a very social area, which is where I met Jill, actually. And so I just enjoy going to restaurants and clubs and hanging out and talking to people.

[C]

You over this girl?

[D]

Yeah.

[C]

You are older? Yes.

[D]

37.

[F]

37, okay. That's good.

[C]

Okay, what else?

[F]

What's your sign?

[C]

What girly questions can y' all ask?

[E]

Yeah, what's your sign?

[D]

Libra.

[E]

Libra.

[F]

Okay. Libra.

[E]

Some people.

[F]

That's 37. Have you ever been married?

[D]

No. No kids? Never married.

[E]

Okay.

[C]

Any long term relationships?

[D]

A few.

[C]

How long? What's the longest?

[D]

Two years.

[C]

Two years.

[F]

Okay. Two years. Okay.

[C]

Most romantic thing you ever did for a woman?

[D]

Took her on a cruise.

[C]

Tried to take her on a cruise. You say that you've traveled a lot. Where are some of the places that you've gone?

[D]

I had a friend that lived in Amsterdam, so I traveled with him around Europe, went skiing in the friend shops and went to London and Paris and mostly Europe.

[E]

What was your favorite place in Europe?

[D]

I think Paris was fun.

[E]

Okay.

[C]

When's the last time you cried?

[D]

What?

[C]

When's the last time you cried? Trying to show your sensitive side.

[D]

It's been a few days. Saw a good movie.

[C]

What'd you say?

[D]

I don't remember.

[C]

But you cried over a movie?

[D]

Yeah.

[C]

What was it?

[D]

I don't remember.

[C]

Now this is very defining right here.

[E]

You're not about to give him crap, are you?

[D]

No.

[C]

I want to know what it is, though. But it's very, very defining, I think, for a woman.

[D]

I actually don't remember what the movie was, but I do like. I do like emotional movies.

[C]

So. Talladega Nights? Because I busted up at the end of the thing, too. Buckeye didn't. Sure.

[F]

Are you a religious guy? Spiritual guy?

[D]

I am a Christian, but I wouldn't say I'm spiritual.

[E]

Okay.

[C]

Feel like we're pulling teeth here. Richard, give us something.

[E]

I know you feel awkward.

[C]

The whole thing is awkward.

[F]

It's like the first day.

[D]

Would you be willing to put Dudoir photos online so women can see exactly what they're getting? No.

[C]

All right, here's Shel, who can vouch for you. Good morning, shel. You're on Q100.

[G]

Good morning.

[C]

Hello.

[F]

Hey.

[G]

I just called because I heard a friendly voice on the line, and I'm calling in to vouch for Richard.

[C]

All right. What can you tell us about him?

[G]

I work with Richard. We've worked together for several years. We've traveled on business and hung out as friends. Used to play tennis together. You know, we've just done the normal stuff. He's a great guy, a good catch for anyone.

[C]

So you would recommend him to one of your girlfriends?

[G]

Absolutely.

[C]

Okay, well, if you have any. Girlfriend, Michelle, you have any? Yeah, they can go on a cruise in just a couple of days.

[G]

If you do, I'll start dialing for digits to see as long as I

[F]

got a passport and a week off.

[C]

That's right, you're good to go. Here is Emily. Good morning, Emily. You're on Q100.

[G]

Good morning, bird Show.

[C]

Hey, Emily.

[G]

How are you guys doing?

[F]

Good.

[C]

What's up?

[G]

I'm just calling because this is very intriguing and it sounds like my kind of thing.

[C]

Okay, Emily, Richard. Richard, Emily. Go ahead, Emily.

[D]

Hi.

[G]

No, I love to cruise. I usually cruise. I don't know, at least once or twice a year. And for the past two and a half years, I haven't been able to. And I always try to take time off in January, so I'm going to be doing that.

[D]

What about you, Emily?

[G]

What would you like to know?

[D]

What do you look like?

[G]

I am. Let's see. Well, first of all, I'm 37. I have blonde hair and blue eyes. And I guess he would describe me as cute and fun and petite and, I don't know, people say I'm attractive. I think I'm somewhat attractive. And I think it's more my personality that is important, very fun, and just like to try new things.

[C]

All right, here's how I think we're gonna handle this. We're gonna put up two ways that you can communicate with Richard here, okay? And he is gonna go out with as many of you as he wants to over the next 24 hours. So he's gonna go out to either lunches or dinners or talk to you on the phone or do email back and forth, whatever, and then he'll come in here tomorrow morning and go, look, I had four dates yesterday. They lasted 20 minutes. Here's who I'm taking on the cruise. Or it might not be anybody, right? You know, who knows how many emails or how many calls we'll get.

[F]

You needed to, like, set up shop somewhere and just have people come in, like, Interviews.

[D]

Okay. Yeah.

[G]

Seriously crazy fun, right?

[C]

All right, so again, I mean, you have to be available on the 29th. You have a passport, right?

[E]

Mm.

[C]

You gotta get your butt on down to Tampa and then from there, Richard's gonna take over.

[G]

Okay.

[C]

All clear.

[G]

Very clear. It sounds like an adventure.

[C]

You get your ass on down to Tampa. Richard gonna take care of that ass after that. All right, so we set up an email address and it's online right [e-mail] I would suggest because Jen's first thing was, well, let's see a picture of him. I think that's only fair that if you send him a picture also.

[E]

Sure.

[F]

Yeah. Definitely exchange pictures and, you know, as much information as possible, like as if you were online dating, but just much more quickly.

[C]

Right, right. I mean, it's this. The turnaround on this is very, very quick. You gotta be gone on the 29th. Gotta be in Tampa on the 29th. All right, Richard, anything else you want to say before I give the phone number out for the voicemail also?

[D]

No.

[C]

No. You're ready. You ready to do this?

[D]

Ready to do this.

[C]

It's a strange, isn't it?

[D]

It's fun, though.

[C]

It is. Let's see what we can find.

[D]

All right.

[C]

All right, the email is up online right [e-mail] so is his picture. Or you can call him. We are taking the. The retail rant line and we're just gonna use that one over the next 24 hours. 404-255-3535. But give us a couple of minutes and then Richard will call some of you guys back here, you know, after the show and say, look, let's meet for lunch today. Or you have time at 2 o' clock and he may spend 20 minutes with you. He may spend 10 minutes with you. It may just be a phone call, but he's got to do this quickly. He's got 24 hours to choose one of you to go on this vacation with him down to the Caribbean.

[A]

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[C]

Good luck.

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[D]

Com.