Vault: His Cruise Date Turned Into The Worst Experience Ever!

Summary

The Bert Show – “Vault: His Cruise Date Turned Into The Worst Experience Ever!”

Date: March 16, 2026

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Episode Overview

In this episode, The Bert Show revisits the aftermath of a much-anticipated—and ultimately disastrous—“blind date” cruise experiment. Richard, recently dumped but still holding cruise tickets meant for his ex, sought a new companion through the show. Listeners helped select Christy as his last-minute cruise partner. The team checks in with Richard and others connected to the trip to dissect what went wrong (and what went right), offering a vulnerable, funny, and honest debrief of sharing close quarters with a near stranger.

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Major Discussion Points & Insights

Setting Up the Cruise Date

• Recap of the Contest: Richard’s original girlfriend broke up with him before their scheduled Caribbean cruise, prompting the show's unusual contest to find him a new travel partner with just “two days to find her” (01:01).
• Christy’s Mindset: Christy initially entered the contest as a joke, pushed by a friend. When chosen, she grew “nervous and a little apprehensive” (01:53), but ultimately decided to go along.

Social Awkwardness & Realities of the Setup

• Realities of Traveling with a Stranger: The hosts and Richard discuss the inherent challenges of close-quarters travel, even with established partners, noting, “Now you add to the equation here, a cruise... you’ve never had anything except an hour conversation” (02:31).
• Comic Relief: The team lightens the mood with jokes about cruise staterooms and forced intimacy, e.g., “Running the shower in the bathroom's gonna be enough to cover up your farts. Like, she's going to hear it.” (03:01).

Onboard Dynamics: Chemistry or Lack Thereof

• First Impressions: The pair share drinks and small talk but find day one “awkward.” The stateroom is not as cramped as feared, but “it was definitely awkward hanging out that much with someone that you don’t really know” (05:04).
• When Did It Go South?: By the second day, both acknowledged zero romantic chemistry, and decided to “just have a good time, make the best of this” as platonic companions (06:33).
  • Quote – Richard: “I think by the second day we realized we’re not really compatible.” (05:58)
  • Quote – Host: “So, second day of a five day cruise, you realize you’re not compatible.” (06:03)

The ‘Wingman’ Pivot & New Friends

• Making the Best of It: The pair agree to be each other’s wingman/wingwoman rather than force a romance. Richard describes the experience as “about a 4” out of 10 (07:18), but concedes it may be higher due to the cruise’s setting.
• Meeting Bill & Ann from Ohio: Formal dinners introduce them to a married couple, Bill and Ann, who become their primary companions and help ease the awkwardness.

Honest Reflections – Richard and Ann’s Perspectives

• Richard’s Summary: “It was an adventure... I don’t recommend a five day cruise as a second date, but it was fun.” (15:24)
• Ann’s Take: Ann describes the couple as “really, really cool people,” confirming that chemistry was clearly lacking but insisting they didn’t ruin her vacation (13:01).
  • Quote – Ann: “We just kind of were wondering how the conversation was going when we weren’t around.” (10:21)
  • “Richard was really funny, and, you know, he just wanted to have a good time. He’s a total gentleman, and any woman out there would be lucky to be with him.” (13:01)
• Silences & Social Dynamics: Ann notes the group dynamic shifted as the pair began sitting apart, and awkward silences grew as the cruise went on.

How Awkward Was It, Really?

• No Major Drama – Just Silence: There was no fighting or arguments, just escalating discomfort and “stretches of silence.”
  • Quote – Host: “But it was a four. A four is a bad trip.” (09:01)
  • Quote – Richard: “I think we’re just two different people.” (11:02)
  • Christy even skipped dinner one night rather than join Richard and the group (13:28).
• The “Talk”: They had an explicit conversation establishing there would be no romance, after which Christy began distancing herself.
  • “After you had that talk... she started sitting on the opposite side of our friends” (14:10).

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Notable Quotes & Memorable Moments

• On Cruise Date Risks:
  “I don’t recommend a five day cruise as a second date, but it was fun.” — Richard (15:30)
• On Chemistry:
  “By the second day, we realized this isn’t really, you know, we’re not really compatible.” — Richard (05:58)
• On Trying Anyway:
  “At least you tried. Yeah. You had an experience.” — Host (15:24)
• Ann’s Endorsement:
  “If I knew anybody, I would set him up in a heartbeat because he’s a sweet guy... it’s just one of those things that just didn’t work out.” — Ann (13:01)
• Hosts’ Comic Banter:
  The hosts fill awkward silences with banter about “cat sweaters,” swingers, and the weirdness of forced social proximity.

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Key Timestamps

• [01:01] – Recap of Richard and Christy’s selection and previous appearance
• [03:13] – Richard returns to recount the cruise
• [05:04] – First-night awkwardness and stateroom logistics
• [05:58] – The realization: no chemistry
• [07:18] – Rating the trip as a “4” out of 10
• [08:19] – Enter Bill and Ann from Ohio
• [10:21] – Ann observes and comments on the couple’s awkwardness
• [13:28] – Christy skips dinner, distancing herself
• [15:24] – Final reflections; “At least you tried.”

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Overall Tone

The tone is candid, self-deprecating, and light-hearted, mixing humor with empathy as The Bert Show crew and guests reflect on a well-meaning experiment that didn’t lead to romance, but did deliver plenty of stories—and awkward silences.

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This summary covers all substantive discussion, sidestepping the show’s commercial breaks, intros, and outros, and is designed as a lively, complete replacement for listening in for new or returning Bert Show fans.

Transcript

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[Host (possibly Jeff or main show host)]

the last time that we had Richard and Christie on, this is what she sounded like. He came to us and he said, look, I've got this five day cruise and it was for me and my girlfriend, but she broke up with me and I still want to go on the cruise and I'd like to find a girl that I'm fairly compatible with, but the problem is we only have like two days to find her. So we made that a personal challenge and we took it to you guys and he went out and he talked to a couple of different girls and he decided that Christy was the girl that should go on the cruise with him. And this is what she sounded like the last time we had her on.

[Ann]

I'm looking forward to it. A little nervous, a little apprehensive. I had really low expectations. Like I was expecting to go and meet him for a drink and you know, not really like him, but he was actually, you know, funny and we had a lot to talk about and yeah, so why not?

[Richard]

Okay.

[Host (possibly Jeff or main show host)]

At that point she sounds pretty excited, but Wendy said by the end of the conversation you say she sounded a little apprehensive.

[Co-host or commentator]

Yeah, she sounded a little nervous, like she didn't want to go but she got picked so she had to go.

[Bill]

Yeah, the way it came about was like she entered it originally as a joke, like a friend of hers.

[Richard]

Right.

[Bill]

Sent the first line in and then when she actually progressed down through the vetting procedure and found out that she was process. I mean, she. And found out that she was really gonna be one of the finalists. She was kind of like, oh, okay, it's cool. Cruz started as a joke.

[Richard]

Okay. Yeah.

[Co-host or commentator]

So.

[Host (possibly Jeff or main show host)]

So the reality was hitting her.

[Co-host or commentator]

Well, you know, I just interpreted it as she's nervous and here she is getting picked and it's, you know, it's. It's gonna be an awkward situation to. Even if it turns out fine. So I didn't really read too much into it.

[Host (possibly Jeff or main show host)]

And I said this earlier. You know, when you travel with anybody, it doesn't matter how long you've been with them. I mean, my wife and I just went on vacation. We've been with each other for 14 years. It's tough to travel. You want to do one thing, she wants to do the other. You want to eat here, she wants to eat there. You want to chill out, she wants to go on a tour. So it's always a little bit of, you know, compromise going on. Now you add to the equation here, a cruise where your stateroom is all of about eight by eight and you're basically right on top of each other. And you've really never had anything except an hour conversation.

[Richard]

So.

[Host (possibly Jeff or main show host)]

So anything can happen at that point.

[Bill]

Like, you can't. It's not a situation where running in the water in the. Running the shower in the bathroom's gonna be enough to cover up your farts. Like, she's going to hear it.

[Host (possibly Jeff or main show host)]

You're gonna have to tell her. You're gonna have to go to another deck.

[Bill]

Right.

[Host (possibly Jeff or main show host)]

So here is Richard back from his cruise. How are you?

[Richard]

Good, how are you?

[Host (possibly Jeff or main show host)]

I'm okay. All we ask for you because we did do this whole thing to try to find you the right girl, is just give us some brutal honesty on exactly what happened. Because from the time you left here, things look pretty good. Guys are ready to go, Ready to do this five day cruise together.

[Richard]

Yeah. At first she was a little apprehensive, but she actually showed up at the airport, which was a big step.

[Host (possibly Jeff or main show host)]

Were you shocked?

[Richard]

I was shocked. She pulled up and I could at least have a ride to the ship. And we got on board, laid around the pool, had some drinks, had some conversation. It was a little awkward the first day. Just trying to get to know each other and you know what's going on. Who's.

[Bill]

So it went very fast. How does it go when you get to the room? Because cruise ship beds are either two separate small beds or they've removed the dresser and they kind of push them together.

[Richard]

Well, they're two separate beds. It wasn't an issue.

[Host (possibly Jeff or main show host)]

Okay, but you were at the hotel before that for a whole night? No, no, no, no. Right to the cruise.

[Richard]

I flew that morning and then she picked me up.

[Host (possibly Jeff or main show host)]

Gotcha. Okay.

[Richard]

So, yeah, I mean, we spent second day basically at sea, lounging around in the sun, having frozen drinks, relaxing. Not a lot of conversations.

[Bill]

Well, hold on a minute, hold on a minute.

[Host (possibly Jeff or main show host)]

All right, sorry. We're going awfully fast. Actually, I'm with Jeff on this. We're accelerating too fast. Like, because you pret. In the first five minutes of a conversation things are going to go well. Or not.

[Bill]

Yeah, you're yada yada in this. So you get on the boat and then everything's great. Then you have some drinks. Right. And things are. So did either of you get good and buzzed?

[Richard]

Yeah, I'd say so.

[Host (possibly Jeff or main show host)]

Both of you?

[Richard]

Yeah.

[Host (possibly Jeff or main show host)]

Okay.

[Bill]

All right. So then you. Then you know, fast forward. Drink, drink, drink, Dance, dance, dance. Fun. Then it's bedtime. So what happens when you're in your little closet and you're doing your little dance where you're trying to put on your pajamas and she's trying to put on her full length nightgown that goes up to her neck and you guys are like trying to work, she's trying

[Host (possibly Jeff or main show host)]

to get all Amish, right.

[Bill]

And you guys are trying to your way around that tiny little room and then you go to bed. Is it like, okay, good night and shake hands or kiss? Or do you try to make two people fit in one bed or what happens?

[Richard]

Yeah, actually the state room is a lot larger than I thought it'd be. Oh yeah, There was quite a bit of room. It was definitely awkward hanging out that much with someone that you don't really know.

[Co-host or commentator]

Sure.

[Richard]

It wasn't that bad. I gave her her space. I'd go off, do something else while she got ready and I'd come back. So it wasn't too bad.

[Bill]

And she was in bed with the sheets pulled right up to her neck tightly. Yeah.

[Richard]

The first night with another guy. With someone else.

[Bill]

But then what it like, are you guys lying in your separate bed and you go, good night? And she goes, good night?

[Richard]

Yeah, kind of like that.

[Host (possibly Jeff or main show host)]

It was okay. Could you tell during that first day, I still feel like we're missing here the first day that you guys are out cruising and you're drinking and you're lounging around and stuff. Are you getting any kind of sense at all that there's any kind of Chemistry here or do you know, like right off the bat, okay, this is going to be nothing but friendship.

[Richard]

I think right off it was, let's just see if we get through the first day chemistry. Give me a drink unknown. There was a lot of drinking maybe to get through that. But I think by the second day we realized this isn't really, you know, we're not really compatible.

[Host (possibly Jeff or main show host)]

So the second day of a five day cruise, you realize that this is not, you're not compatible.

[Co-host or commentator]

But are you getting along? I mean, we're getting along right now. It could be platonic and fun and hanging out and looking for other people while you're on the ship together and having a good time.

[Richard]

Definitely. And I would say she was definitely a great pick because she was a lot of fun, she had great personality, she was definitely someone that could.

[Bill]

All the guys loved her.

[Richard]

Yeah. So, yeah, a good choice. However, not something, you know, long term compatibility. But that wasn't really what I was looking for. I mean, ideally, sure, but you know, I just needed someone to hang out with on the cruise and have fun and she definitely was that person.

[Bill]

Do you, do you acknowledge that, like halfway through the second day, are you like, yeah, this isn't gonna be anything romantic, so you be my wing woman, I'll be your wingman, or are you like, let's just drink until we're hot and we'll have sex? Or like, what is.

[Richard]

No, there's no sex. It was pretty much, hey, this is how it is, you know, cards on the table, let's just have a good time, make the best of this.

[Host (possibly Jeff or main show host)]

You said that or she said that?

[Richard]

I brought it up and she confirmed.

[Host (possibly Jeff or main show host)]

Okay, so you weren't feeling any kind of vibe? If she was vibing on you, would you have been vibing on her?

[Richard]

I don't know.

[Host (possibly Jeff or main show host)]

Not sure.

[Richard]

It's hard to say.

[Host (possibly Jeff or main show host)]

So this is day two in a five day cruise. So those other three days, are they on a scale of one to ten, with ten being the best time you've ever had in your life. It's a mentos commercial and one being just awful.

[Richard]

I'd say it's about a 4.

[Host (possibly Jeff or main show host)]

4.

[Richard]

You know, it's the Caribbean, you gotta have some fun. But fortunately, at formal dinner, we had dinner with Bill and Ann, who was a fun married couple out of Ohio. And we hung out with them.

[Bill]

Bill and Ann from Ohio are like the most boring people on the planet.

[Richard]

Hey, be nice.

[Host (possibly Jeff or main show host)]

She's on the phone.

[Co-host or commentator]

Yeah, she's on hold.

[Bill]

I'm not saying she is. I'M just saying. Hi, I'm Ann. This is my husband Bill. We're from Ohio. And I'm like, oh, great.

[Host (possibly Jeff or main show host)]

It just sounds very geriatric. I mean, generic.

[Bill]

Wow, that is a nice looking cat on your sweater.

[Co-host or commentator]

It's great.

[Host (possibly Jeff or main show host)]

And it's 94 degrees out. All right, so you sit down at this formal dinner and you make friends with other people, and things are going okay there.

[Richard]

Right?

[Host (possibly Jeff or main show host)]

All right.

[Richard]

Yes. And they were very cool, Jeff, so.

[Bill]

No, I'm not saying that they're not. I'm sure they are.

[Co-host or commentator]

It was a dog on a sweater.

[Bill]

I'm just saying Bill and Ann from Ohio wear reindeer ears during Christmas when they go to the mall.

[Richard]

All right, So I think that that helped get us over the hump because it was like, okay. We realized this isn't really going anywhere, but. Sorry about that. So, yeah, we hung out with them most of the rest of the cruise, and they made it a lot more fun.

[Host (possibly Jeff or main show host)]

Okay, we need some honesty here, because if things are just platonic and you're having a good time and she's having a good time, and you get back to Atlanta, that's a seven. That's an. It was an average trip. Look, I didn't get any. But we had a good time, and I'll never forget it. Something happened to bring it from a seven to a four.

[Co-host or commentator]

Did you fight?

[Bill]

Did she hook up with another dude in your room?

[Richard]

I got kicked out of the state room the last day. That was awkward.

[Host (possibly Jeff or main show host)]

No, I'm just kidding.

[Richard]

No, she didn't. No, it was.

[Bill]

Did she hook up with another guy?

[Richard]

No, not that I know of. It's a big shit.

[Host (possibly Jeff or main show host)]

There was never any kind of argument?

[Richard]

No.

[Host (possibly Jeff or main show host)]

Any kind of dislike?

[Richard]

No.

[Host (possibly Jeff or main show host)]

But it was a four. A four is a bad trip.

[Co-host or commentator]

It is bad.

[Richard]

Okay, maybe it's not a 4. Maybe it's a little higher than that, but 4.2. Yeah.

[Bill]

Why isn't she on with us?

[Richard]

She had a meeting today so she couldn't get out of it.

[Host (possibly Jeff or main show host)]

Why is she really not on with us today?

[Richard]

That's the truth. You can call her and ask her.

[Host (possibly Jeff or main show host)]

I can't. She's in a meeting.

[Bill]

She can't.

[Richard]

She won't talk.

[Host (possibly Jeff or main show host)]

Here's Ann from Ohio.

[Richard]

Hey, Anne. Hi.

[Host (possibly Jeff or main show host)]

How are you?

[Ann]

Just for the record, I don't want cats on my sweater.

[Richard]

All right.

[Host (possibly Jeff or main show host)]

And what did you see? Because he said, like, the highlight of this trip was hanging out with you and your husband. So what did you see with these two?

[Richard]

Of course.

[Ann]

We're fun people. Come on. We're Ohio State Buckeye fans. We know how to party. Come on, gator chomp.

[Host (possibly Jeff or main show host)]

We'll see. So tell us about the night that you guys hung out with them. Could you tell that there was zero chemistry going on there?

[Ann]

Well, we met him the first night at dinner, and, you know, they could have totally played it off as a normal couple and we wouldn't have known anything. But the first question I asked was, what made you decide to take a cruise? So they had to tell us the whole story about how they met on the radio and everything. So everything was out in the open from the beginning. And, yeah, by the second night, we could kind of tell that it probably wasn't going to work. Just not much chemistry. And, you know, we tended. My husband and I tended to carry the conversation a lot, so we just kind of were wondering how the conversation was going when we weren't around.

[Host (possibly Jeff or main show host)]

So was there a lot of conversation going on at all when they weren't around?

[Richard]

Not really.

[Host (possibly Jeff or main show host)]

Nothing.

[Richard]

Damn. That was the worst part.

[Co-host or commentator]

That's the worst. It is when you're in a car and you don't know what to say and both of you are sitting there, it's the longest drive ever. That is the feeling is if you

acknowledged it, if you acknowledge it, nothing was going to happen then that could have been a potential for such a fun trip, you know, that's out of the way. You know what? She knew. She came on last minute because you and your girlfriend didn't work out. Because. Because that ended up.

[Richard]

Could have.

[Co-host or commentator]

You could have had more fun with her than you would have your girlfriend if you'd been fighting the whole time.

[Host (possibly Jeff or main show host)]

Unless it's just some person that even platonically, you wouldn't even hang out with, even as friends. This is somebody in the office that you have nothing in common with. You got nothing.

[Co-host or commentator]

Word.

[Richard]

I think we're just two different people.

[Bill]

Did she at any point, say, in the cruise, I'm not coming back on the radio?

[Richard]

No, she was still planning on it, I think, until the end, where she conveniently had a meeting.

[Host (possibly Jeff or main show host)]

Okay, so. And you guys were assigned the same table. So you guys ate with each other every night?

[Richard]

Yes.

[Host (possibly Jeff or main show host)]

I see. So did the relationship slowly deteriorate in front of you, or it just. It was just never even there.

[Ann]

After the second night, it pretty much tended to get worse and worse. And, I mean, we had a fun time and we talked at dinner, but then we started hanging out a little bit more out on the ship and stuff. And then it got more and more awkward as the Cruise went on.

[Bill]

So, like, what was awkward? Just big stretches of silence or, like, were there. Was it like. You ever been out with a couple who starts fighting? I know Bill and Anne don't have any couples that fight, but if you did, like, you know how sometimes. And, you know, the other couple's fighting, but they're not acknowledging that they're fighting, but it's just like, hi, Wendy, may I have the salt? If you're not doing anything else, like our neighbor, please.

[Co-host or commentator]

Did they just look miserable?

[Ann]

No. I mean, it wasn't really fighting, but it kind of got to the point where we would go and do something, and Christy would sit on the left side of me, and then my husband was the other side, and then Richard would sit on the other side of him. So they would sit separate from each other.

[Host (possibly Jeff or main show host)]

So you guys were separated by two people?

[Richard]

Yeah.

[Host (possibly Jeff or main show host)]

Okay. But there was never an argument or a disagreement. It was just like.

[Richard]

There really wasn't. We actually got along the, you know, times we were talking.

[Host (possibly Jeff or main show host)]

Okay.

[Ann]

Yeah, yeah.

[Bill]

Did. Do you think they ruined your vacation?

[Ann]

Absolutely not. We had a great time. We had fun. I mean, they're both really, really cool people. I mean, Richard was really funny, and, you know, he just wanted to have a good time. He's, you know, he's a total gentleman, and any woman out there would be lucky to be with him. So if there's any single ladies listening, you know, if I. If I knew anybody, I would set him up in a heartbeat because he's a sweet guy, and, you know, it's just one of those things that just didn't work out, and it's.

[Host (possibly Jeff or main show host)]

It was almost an impossible scenario. I mean, you talk about a long shot. What are you looking like that for, Melissa?

[Co-host or commentator]

No, I'm just listening. I'm listening because there is an. I just feel like it's a. If there's no tension, if there's no true awkwardness, I just feel like it's a. I don't know. I feel. I don't know. I feel like it's a wasted potential fun time. Even though this is a very well

constructed sentence, was there one day where you just didn't see each other? You woke up in the morning, didn't see each other all day, and saw each other at night?

[Richard]

Not the whole day, but yeah, there were. Near the end, there were some spaces. She didn't show up for dinner one night, so.

[Bill]

Really?

[Host (possibly Jeff or main show host)]

Really, she just bailed?

[Richard]

She was, you know, tired.

[Host (possibly Jeff or main show host)]

Did she tell you that she was gonna crash in the cabin or did she Just not show.

[Richard]

Yeah, she said she was going back to the cabin and she just didn't show up for dinner. Okay.

[Host (possibly Jeff or main show host)]

All right.

[Bill]

That's weird.

[Host (possibly Jeff or main show host)]

Well, the whole thing is weird.

[Bill]

Like the fact he didn't even show up. Like, I mean, he still is footing the bill for it.

[Co-host or commentator]

Yeah, I just. Was it established that there was never gonna be anything going on on the trip, or was there always the potential? Because I feel like if there was always the potential and she was just trying to avoid it. Avoid it.

[Richard]

I mean, I think at first there was the unknown, and then a few days in, it was. You know, we had the talk and.

[Host (possibly Jeff or main show host)]

And that should have been it.

[Co-host or commentator]

That should have made it fun.

[Richard]

Okay. And it was from that point on where she started sitting on the opposite side of our friends.

[Host (possibly Jeff or main show host)]

Oh, really? After you had that talk? But you say you're. And you're the one that initiated the conversation.

[Richard]

Well, I just brought it up and said, hey, you know, let's talk about what's going on. And we agreed it was awkward and that there's no chemistry and, you know, let's just have a good time.

[Host (possibly Jeff or main show host)]

Okay, cool.

[Bill]

At that point, I'd just be like, the hell with it. Deuce in your own bathroom. No need to go down to the bar.

[Host (possibly Jeff or main show host)]

Thanks, Anne.

[Bill]

I mean, you're paying for it.

[Host (possibly Jeff or main show host)]

Bye. Bye.

[Richard]

Thanks, Anne.

[Host (possibly Jeff or main show host)]

Ann.

[Ann]

Yeah.

[Host (possibly Jeff or main show host)]

Goodbye.

[Ann]

Bye. Thanks.

[Bill]

Anne's on a soap opera. Bill and Ann from Ohio. They're on Young and the Restless. They don't say goodbye with anything.

[Co-host or commentator]

The whole conversation's been awkward.

[Host (possibly Jeff or main show host)]

I think that's right. I want some space. I want some more space between you and me right now.

[Ann]

I'm uncomfortable.

[Bill]

I think the problem in your relationship with Christie was Anne. She's definitely into you, which made Bill uncomfortable, but nobody knows this, but Bill's actually. Bill and Anne are actually swingers. They have a dungeon in their basement.

[Host (possibly Jeff or main show host)]

It's the ones that you never think would be swinging or really swinging.

[Co-host or commentator]

They wear cat sweaters. They don't swing.

[Bill]

That's just to cover up cat sweaters. But they got cover the sweaters in the summertime to cover up her fierce nipples.

[Co-host or commentator]

Oh, my God.

[Bill]

Totally.

[Host (possibly Jeff or main show host)]

Richard. You tried.

[Richard]

I tried.

[Host (possibly Jeff or main show host)]

At least you tried, man. At least you tried. Yeah. You had an experience.

[Richard]

It was an adventure.

[Host (possibly Jeff or main show host)]

You'll never do it again, that's for sure.

[Richard]

I don't recommend a five day cruise as a second date, but it was fun.

[Host (possibly Jeff or main show host)]

Probably not even gonna call her. No, probably not.

[Richard]

Okay.

[Host (possibly Jeff or main show host)]

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[Co-host or commentator]

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[Co-host or commentator]

listings and see cars based on my budget.

You can really have it delivered or pick it up. Mommy's I think kid is walking up the the slide.

Really?

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