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Ray
This is an iHeart podcast. Guaranteed Human Ryan Reynolds here from Mint
Lunchbox
Mobile with a message for everyone paying
Ray
Big Wireless way too much.
Lunchbox
Please, for the love of everything good in this world, stop with Mint. You can get premium wireless for just $15 a month. Of course, if you enjoy overpaying. No judgments.
Ray
But that's weird.
Lunchbox
Okay, one judgment anyway.
Ray
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Lunchbox
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Ray
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Lunchbox
Good man. Hey, this is it. Guys, we're headed down to Jamaica, mon. Oh, my goodness. We have been waiting for this for weeks, days, months, and we are finally gonna hear about Jamaica, mon. Jamaica.
Ray
You Jamaican me crazy after the break.
Lunchbox
No, no, we're not taking. We've been doing it for 26 seconds.
Ray
We're not doing teas.
Lunchbox
We're not doing a break. But before we get to Jamaica, I mean, I need to know, like, going into Jamaica. Like, I need to know the process of Jamaica, getting to Jamaica. I need to feel what it's like to leave American soil and touch down in Jamaica. I need to know, like, do you have an early flight? So right when you get in, you can see the beautiful beaches. The sun is still shining. Is it a nighttime flight? So you have to wait to enjoy Jamaica till the next day? This. I need to set the scene in this first, you know, little segment, I would say. Instead of dropping right into the Jamaica story, I need to know how we got there. I want to set the mood, man.
Ray
Mon, they have land, trees, and sun just like us. No third world country, Ray. How poor, really, are they?
Lunchbox
That's not what I'm saying.
Ray
I got you. We hit the airport late.
Lunchbox
You got to see this,
Ray
all right? I'm telling you now.
Lunchbox
No, we'll start the show, and then we got to get into it. Then I want to know, like, bags packed early. Are you panic packing? What am I? That's a stupid question. That's a dumb question, because you're already freaking out about other things, Ray.
Ray
Is it a rush? Like a kidnapping? No, no, no, no, dude. Just packing for an airport, man.
Lunchbox
No, because me, I panic pack, and I pack, like, an hour before my flight.
Ray
That sounds kinky.
Lunchbox
Like, I just. My time management skills are not the best. And we've talked about it on this pod. Like, when we're planning coaches conventions, I'm always like, yeah, I'm gonna get it done. I'm gonna get it done. We're gonna get it done early, early, early, early. And then. Hasn't really happened that way, so that's what I was referring to. But let's just start the show, and then I'll explain.
Ray
We're gonna do it live. We are the 1, 2, 3, soar losers from Jamaica.
Lunchbox
What's up, everybody? I am Lunchbox. I know the most about sports. I'll give you the sports facts, my sports opinions, because I'm pretty much a sports genius, y'.
Ray
All. It's Sizzin. I'm from the north, but this show. I'm from Jamaica. Man, And I got land, man. 2.3333 acres, man. I live with my wife, man. Justin is supposed to be looking after our kid, man, at Vanderbilt, man, but Justin moved to Michigan, man, for the foreseeable future, man, which is thousands of miles away from Jamaica and thousands of miles away from Nashville, Tennessee, man. Over to you, man, but probably then back to me, man.
Lunchbox
Yeah. So as you're headed out for Jamaica, are you packed days in advance?
Ray
Bazer is, because she works from home, and she's able to do that. Oh. Pack a hat one day, bra the next, panties, thong, you know, so she's me. I would almost say. What is it? What do you call it?
Lunchbox
Panic packing.
Ray
Kinky panic.
Lunchbox
No, no. Panic packing.
Ray
So, like, yeah, I'll like, kind of foreplay, like, choke myself and panic and then pack an hour before.
Lunchbox
Okay.
Ray
I'm similar to you. I'm doing laundry at 2am in the morning if we're leaving at 5.
Lunchbox
Thank you. That's how I pack, and my wife hates it. It drives her nuts that I just am like, ah, you know, I'll get. We've got to be at the airport in three hours. I'm like, yeah, so that's plenty of time to do two loads of laundry, figure out what I need, put it in a suitcase, and we can roll it to the airport. That drives her insane. So you aren't panic. You're panic packing. Bay is packed. Do you bring sunscreen, or do you
Ray
buy sunscreen fully loaded, used? About one bottle of the 10. So remember that, guys, for the cruise and for the next convention, you don't need all the sunscreen you're gonna pack.
Lunchbox
Okay? And so how are you going airport? Is Phil taking you? Are you driving, leaving your vehicle? You Ubering?
Ray
What?
Lunchbox
What's the plan? Getting to the airport?
Ray
Bring our vehicle, and VIP park where you park? Right next to the airport. Rich, Rich, don't ever let Bayser do it, because there's no turning back. Once you give a street cat satin sheets, they never go back to the street. We learned that if you take an Uber, it's just awkward. And that's not how you want to come back to America. Their exit or entrance. And then also when you park there, you realize you still pay 18 a day. If you VIP, it's 28. It's $10 more a day for VIP. They warm your car, they wash the thing. Heck, I think the guy farts in the seat before you get there. It's great. You. You get off the airplane and your car's waiting for you.
Lunchbox
It is pretty fantastic. I used to do one of those services. You park off property and we had a deal with the station here and one of the companies and so they would wash your car and they would have it started and they would shuttle, would pick you up, drive you right to your car.
Ray
Boom.
Lunchbox
You're in and out in five minutes. Placement, belly up, it's no longer there. So now I just pay the outrageous prices that it costs to park at the freaking airport.
Ray
Well, you know who taught me that? Coach. Ah. He said, hey, dude, nobody knows about it. You can park right there and you live like a celebrity. And it's not very expensive.
Lunchbox
I did it one time when I was going to Florida to my family was already down there and we were working and we were going to be Friday and Saturday, Sunday. I was going after the show Friday and I mean, I had a flight at 1:30 and we were at the building till 12:30 and I had to get on the airplane. The plane was leaving Nashville in one hour from when we said, okay, everybody have a good weekend. And I drove so fast to the airport. Like, I mean, so fast. No, no, no. There was a fire truck hit the fire truck.
Ray
Well, it's this thing.
Lunchbox
Oh, never mind. We don't need that. There was a fire truck with its lights on and I was passing it on the highway because I did not want to miss my plane. And I said, that is a bad sign when I am driving that fast to get to the airport.
Ray
Why'd you pass me? Why'd you get a. Give me a ticket? I don't know. You passed a fire truck with its lights on.
Lunchbox
And I pulled up to this vip. You got me this VIP thing that you are talking about. And I said, hey, man, I need a ticket. I need a ticket. He said, oh, sir, you're at the wait in line. You know what I mean? There's two cars in front of you. I said, man, I'm going to miss my flight. He goes, sorry, man. And I said, all right, I'll just leave the car, the keys on the seat. Do you really want to just leave your car there with the keys on the seat? Yeah. I was like, yeah, I'll just find it when I get back.
Ray
Then to find out.
Lunchbox
I'll just find it when I get back. Pull up because you think it's going to be just that easy. We'll just be able to find the car where the guy didn't take a ticket.
Ray
Dude, you argue with everybody. I don't even say, but One word to the VIP person. Keys. Hi, see you Sunday.
Lunchbox
I was in such a hurry that I was going to miss the flight that I was just going to leave the keys, not even get a ticket and figure it out when I got back.
Ray
Then to find out.
Lunchbox
And then I pulled out a $10 bill or $20 bill and he goes, oh, here's your ticket right now. Boom. Made the flight, but go ahead. So you're going to park in vip?
Ray
Sorry, we're not even out of the airport. Dude. I know this Jamaica story is going to be a two parter.
Lunchbox
So you go and.
Ray
Right, you go to gate D. No, no.
Lunchbox
Are you flying out in the morning or the evening? The afternoon. What time are you leaving Nashville?
Ray
This trip was so long ago. Let me go back in my head. I believe it's always early flight. So yes, it was wee hours of the morning. We probably left at 6am thank you.
Lunchbox
I just want to know what it's going to be like when we get to Jamaica. Is it going to be daytime?
Ray
Well, that's the problem. It was going to be where we could sneak in one hour of sunlight. Well, in Florida, because we had connecting flights, we hit a bird, we had to return back to Orlando or Miami or Fort Lauderdale. One of the three, don't know, had about three times that many drinks. And so then we were delayed and we didn't get in probably till 10pm no. So we couldn't squeeze in the hour of sunlight and we couldn't even do a dinner. Come on. So that's also why we got the pro tip that sometimes you go a day before your reservation because you still get charged for that day.
Lunchbox
Oh man, that's rough, man.
Ray
Oh, we there for five bangers, so we almost got four and a half.
Lunchbox
I had no idea that there was travel delays because of birds.
Ray
That's what he said. He said because of it maybe blocking the engine that we had to turn around. And so then you go back to the airport and of course I'm body and drinks. How many can you squeeze in? I told Baser, minimum an hour and a half. They fix it in like 40 minutes. I was still at the bar. I ran back onto the flight as it was basically pulling off.
Lunchbox
Been there, been there.
Ray
I said, well, first of all, reception isn't good in the airport. Never got your texts. And holy crap. Did not know Mr. Coxster here that that pilot was gonna be able to fix an engine with a seagull in it in 40 minutes. Props to him. Hey, where's my seat oh, it's not reserved still. This is actually before the fact when you could have a reserve seat. Now it was fill in, maybe got lucky, sat next to it. Nobody sat in the front seats because it was a bigger dude. Ah. So we sat next to a bigger dude, and he was a recovering alcoholic. I said, I'm in recovery too. Gambling addict. And he goes, here's my drink tickets. So the whole time we're body and drinks right next to this guy recovering from it.
Lunchbox
Wow.
Ray
And he was doing discord. He was on some crazy wacky stuff on his Internet. But we got great seats and two drink tickets, all because we sat next to the big dude.
Lunchbox
What was he head to Jamaica for?
Ray
He wasn't going to Jamaica. So that actually might have been the flight to Florida.
Lunchbox
Okay, got it.
Ray
I was gonna say that dude did not go to Jamaica with us. He was. He would have been burnt like a crab, dude. That guy got off in Florida at some discord convention.
Lunchbox
Hey, Ed, him in a beached whale.
Ray
You know what? Now that you bring it up, it wasn't going to OO Rio. It hadn't seen the sun in like two years. It wasn't going to Montego Bayman.
Lunchbox
All right. Oh, man. Oh, that's funny, man. So you get to Jamaica. Tell me about getting to Jamaica. What's it feel like? Is it hot? Is it like, tell me about Jamaica. What's the. Everybody friendly right when you get off the plane. Hey, welcome to Jamaica, man.
Ray
I believe we're in the vicinity of about 10 drinks each at that point. I remember getting off the plane and this dude was talking my ear off, and he was telling me about this Negril. Gotta go to Negril. He had like his sorority daughter and fraternity son next to him, his wife. It almost looked like the people from the show. That's amazing. Where they're in Europe. Then they go to Taiwan, and it's my favorite show, White Lotus. Yeah, it was exactly like that family.
Lunchbox
Okay.
Ray
And so he's guys going crazy. Looks like a stock trader. The wife looks stressed out and she's on pills maybe. And buddy goes, gotta go to the grill. It's amazing. I go, well, we're actually going to Ocho Rio. So we're not even going into Grill, but he's still pitching me on the grill. I guess we got to check out Negril next time, so remember that. And then immediately, once we get through whatever, we're going through customs, there's a BMW waiting to pick us up, basically with a bow on it. And the guys wearing a Santa hat.
Lunchbox
Let's go.
Ray
I got the pick. We'll put it on the gram.
Lunchbox
I can't wait.
Ray
And so that's it. That we did. You could have paid, I want to say, hundred dollars for a bus with 20 other sweaty Americans now. Or 150 for a VIP. What happened to be a BMW car? I'll do that.
Lunchbox
Yeah.
Ray
And so dude. Dude is amazing. Except for Baser gets with emotional with the dude because he's away from his family on Christmas. It was Christmas Day.
Lunchbox
Oh.
Ray
And so Baser goes, I'm so sorry you have to drive us, Laura. Baser, it's his job. Let him do. And he goes, yeah, I'm just happy to make money. This is awesome. And she goes, I'm so sorry. We're taking you away from your family, Bazer. It's his job. And so I'm sure we tipped the dude $40 after we had already paid him like 150.
Lunchbox
So you paid extra for the parking at the airport. You paid extra for the transportation. You are rich. Rich. Okay.
Ray
But we save up for this. We don't go on vacation on the cheap. If we do it, we've already put an entire five paychecks towards it.
Lunchbox
We get it. You're like, you're trying to be like Joe from Sarasota. I get it. I understand. Trying to impress your hot young wife. I got it.
Ray
And it's also one of those things. There was no gambling there, so. And you weren't allowed to tip there. Oh, yeah, it was some resorts.
Lunchbox
How terrible.
Ray
Well, because some resorts, it's just known, oh, you got to tip the maids or the cleaning people. You got to tip the bar guy. The bar, keep the bar back. The restaurant person at your table at breakfast, $2. Person that turns down your bed, $2. This one, they said no tipping or people get fired. So we still bring 500 because we're going to tip people on the slide, you know?
Lunchbox
Yeah.
Ray
And so the obviously BMW guy, boom.
Lunchbox
You've just slide it. You've been blessed, you've been cited.
Ray
And so two minutes outside the airport, we're stopping, getting some tree. He stopped just for a minute, comes back with entire shrub. We're never going to burn through all that. Maybe all we need is a leaf. You know what I mean?
Lunchbox
Got it.
Ray
And so.
Lunchbox
Got it, man.
Ray
Like Bazer, we've already made two terrible bit money decisions. We give this dude a 40 tip when he's already getting paid. Look at him. He's driving a better vehicle. Than us in America. Like seriously. Seriously. The dude was dried up beams. A BMW? Was it a. No, it wasn't a Benz, it was a BMW and Bazer. I drive a trailblazer from 20 years ago. Good gosh. You don't have to tip the man. And he was a absolute blast and a vibe. But it's dark, so we're not really able to see. You can see some lights up in the hills that what is what Jamaica is cool for. You can see the hills, you can see the shanties, you can see the third world country. Whereas in Costa Rica you can see that too.
Lunchbox
I would say I'm staying out of Costa Rica, man. Surfer dude.
Ray
But places like Aruba and what's in Turks and Caicos and Dominican Republic, there's no hills. So you're just seeing flat at night. You're not going to see anything. This you're seeing the lights. You're seeing what makes it, you know, you're seeing a family. You see Bolt Usain.
Lunchbox
Yeah.
Ray
Seeing flags. They are proud of Jamaica there. But yeah, so you're seeing some stuff thanks to the hills. But it's about an hour and a half drive from this airport.
Lunchbox
Oh my gosh, I'm passing out and
Ray
I still don't even know what airport we flew into. Either it was Montego Bay or OO Rio. Cuz OO Rio is right next to where we were at. So I'm pretty sure we flew into Montego Bay. That's why the flight or the drive was an hour and a half. And the guy at the pool, I'd already told that story. Remember his wife?
Lunchbox
Yeah.
Ray
Very attractive. Massive mountain range. They were hammered. Left the Rolexes at the pool. I kept telling the guy that we flew into Ocho Ria and I told him our. Our drive was an hour and a half. He probably thought I was crazy because it's probably. It's like a five minute drive.
Lunchbox
Yeah, he probably thought this dude doesn't.
Ray
I told the dude the wrong airport for an entire conversation of five hours.
Lunchbox
It happens, man. You're not supposed to know. You're not. You're not Jamaica familiar, you know, you're new.
Ray
He goes, what you went to. You went to Ocho Rio? You. Yeah, yeah, we flew in there, huh? Yeah, it was an hour and a half drive. You went to Ocho Rio? Yeah, you know, bamboo up top, open wide air, you know, not a lot of flights. Yeah, yeah, we gotta take a break. But that guy was so confused. We're still in the car driving to
Lunchbox
the resort man, we haven't got to the resort yet.
Ray
We're at the resort. We just got there. We just got there.
Lunchbox
And they just welcome with open arms or what?
Ray
We did make one more pit stop.
Lunchbox
Let me tell. Let me hear it.
Ray
Bazer didn't know how to properly plant the tree.
Lunchbox
Got it.
Ray
So that guy helped plant the tree while I went to this little dive bar all by myself with American money. And there's 10 people at the bar look at me like, we hate American. Oh, so I didn't. The love from Jamaica doesn't happen until you get to the resort. Up until then, it's a crowd that knows, like, three words. We hate American. I roll up to this bar.
Lunchbox
Hot.
Ray
I got American money. I want some drink. I want some red stripe. I have eight eyes looking at me, and all of them are saying, we hate American.
Lunchbox
They're not your best friend, huh? No, you were. Wait, hold. So you're telling me you were walking in thinking, hey, citizen Raymond Oman. That's what you were thinking. You were thinking, it's gonna be Open arms. With arms wide open. What's that song?
Ray
With arms Wide open. The. The loveman was in the BMW mine when we got picked up. The love man is at the resort, man. But when I was at the dive bar, mom just trying to get a red Stripe, man. They probably overcharged me $20 because I think I gave them a 20 and it was, like, in a dollar beer there. Because their prices are really cheap.
Lunchbox
Yeah.
Ray
And didn't get money back. And then. Yeah. Yeah. They weren't very kind to me there.
Lunchbox
Oh, that's unfortunate.
Ray
And that was really my. For I'm in Jamaica mod. Oh, hey, mom. Bob Marley, man. Boltman. We hate American.
Lunchbox
Oh, like, you walked in and then the. The music stopped.
Ray
Yes. And so then. Then we got out of there, got in the BMW, everything was properly planted, and we were ready to head to the resort.
Lunchbox
Baby, I love it when you pull to the resort. Is there a gate?
Ray
I saw it on the way out. Not on the way in. Things are a little blurry. I'm in and out of consciousness.
Lunchbox
Got it.
Ray
Not really that intense, but I was. Things are a little fuzzy. Okay. There wasn't a gate. I saw it on the way out. But, yeah, we roll up, and it's just. It's beautiful. The Christmas lights. There's presents. Christmas trees lining the row. And there's a huge soldier. A Christmas soldier from. Oh, you know, from all the stories we used to read as kids. They made us feel like it was a Tropical Christmas, the minute we were there. We're at the resort. We need to take a break.
Lunchbox
We're going to go to the front desk. We're going to check in.
Ray
We're.
Lunchbox
We're going to come back and tell you the rest of Jamaica.
Ray
The rest of the story is where we're going to meet after the break. Teddy Bear.
Lunchbox
Teddy Bear. After this.
Ray
So anyways, this Teddy Bear character. So we had actually landed and airported and taxied and got all the way to the resort and what do we need? A nightcap? So you're talking espresso martinis. And we didn't know precisely where the location was where you could go get those. Nice resort. But it's not really signs. They try to make it look all sexy. So we're just kind of looking around when the corner, this dude comes out and he goes, hey, are you guys looking for espresso martinis, man? We go, well, yeah, yeah, yeah, we are. And he goes, I know, man. This really nice place, man. It's just right around the corner. I'll show you, man. And I said, thank you so much, sir. What is your name? And he goes, what? Teddy Bear, man, what are you doing? I started.
Lunchbox
Why, you idiot?
Ray
I only did 30 seconds, you idiot. You didn't miss anything.
Lunchbox
I'm not even did 30 seconds now. I'm all thrown off, man.
Ray
I did 30 seconds, man.
Lunchbox
But why would you do that, man? I was sitting there just waiting for you, and I heard you do your whistle, but I thought that meant you were getting a drink, doing something. And I look in here and he's talking about Teddy Bear.
Ray
I did it to piss you off.
Lunchbox
Ah, you don't piss me off, man. Just confused me more like it.
Ray
Like there's no.
Lunchbox
I'm not angry. I'm just like, huh. So, yeah, I will get. I guess I'll just. Yeah. How long we been doing this now?
Ray
20.
Lunchbox
20. 2020.
Ray
Hell of a documentary, Ray.
Lunchbox
I don't know, 140? Oh, my God. Whatever. So why not just say, hey, lunch,
Ray
I'm ready, man, Is this exact reason to piss you off?
Lunchbox
No, no, no. Do I sound pissed off?
Ray
No, I just did it to see how long I could tell the story before you came in here.
Lunchbox
I was just like, man, Ray went to the bathroom and it's been gone a while. I guess I'll wander down there and see if he's back. Oh, he's already talking. It's in use. The mics are on.
Ray
And I did it to show the listeners that I Could do a show without you. Oh, so for 40 seconds they learned that.
Lunchbox
That's pretty impressive. That's pretty impressive. So are you going to recap it or am I just going to have to catch up?
Ray
Dimly lit resort. It was 9pm and we needed a nightcap. We wanted an espresso Martini. Out of the corner comes this guy, Teddy Bear. Mon, I'll show you where. Espresso Martinis. Arman.
Lunchbox
They work at the hotel or was he a guest?
Ray
Yes. Had the name tag, white shirt, pants. And so we go to the Espresso bar, and it's kind of hidden bookshelves and all that. We would have never found it.
Lunchbox
Wait, wait, wait. There's a special bar for Nespresso?
Ray
Yeah. Espresso Martinis.
Lunchbox
Espresso Martinis. Got it.
Ray
But remember, you can't tip these people. So we get there, and me and Bazer combined have probably put enough drinks down to float a boat. But we're still feeling pretty good. We remember it all. You know what I'm just saying. But if you think about it, heavy travel day, heavy drinking.
Lunchbox
Yeah.
Ray
And we got the free drinks on the flight from that dude. That was a recovery.
Lunchbox
That's right. That was doing his sheets.
Ray
And so we go to this espresso Martini bar. And what do you think? Bazer's already doing the tipping. Hey, I'm. I'm bartender. You were so amazing. Here, here. I know you guys can't take tips. I'm gonna slip you this. So she slips the bartender $40. Teddy bear. We don't know precisely the exact amount, but between 100 and $150, we tip
Lunchbox
Teddy Bear for showing you where the bar is.
Ray
If you ever met us when we're drunk, we're the nicest people in the world.
Lunchbox
Oh, my God.
Ray
And Pacer thinks that everybody's poor. Pacer. This kid probably has a condo. And he was so nice.
Lunchbox
How far did he walk you? Like two stairs?
Ray
Us to the Bobby Montrose studio.
Lunchbox
Oh, my gosh.
Ray
It was a great espresso Martini. And so we wake up the next morning, we thought we got robbed. We realized we tipped Teddy somewhere between north of 100 and south of 200. And that is where the story starts. Teddy Bear.
Lunchbox
Teddy Bear. So I'm assuming that Teddy Bear add to that tip is going to be in your hip pocket all weekend. All week.
Ray
So over the next four days, if we were at a brunch. Oh, hey, Teddy Bear. If we were at a pool. Hey, Teddy Bear. How have you guys been doing, man? Good, man, good Man. Hey, I have my DJ tonight, man. Would you want to swing by and listen to my music, man?
Lunchbox
Maybe.
Ray
Maybe we will after dinner. Hey, man, remember, I'm DJing tonight, man. I'll see you guys later. Thanks, man. Yeah, just let me know. The following morning. Oh, sorry we didn't come, dude. It was late at night. Didn't come. It's okay, man. Later on today, man, we're putting together a skit out here in the plaza. You should come by and see, man. I'll be one of the dancers. Okay? Oh, sounds good. Thank you, Teddy Bear. Yeah, man, no worries, man. If it was a pool, if it was a brunch, if it was a after dinner, if it was a just walking around. Teddy Bear. Teddy Bear. Oh, hey, Teddy Bear. Teddy Bear. Teddy Bear. Teddy Bear. That leads me to the climax of Teddy Bear. So why is Teddy Bear being nice to us? Like, why? Why?
Lunchbox
Because you tipped him so much money.
Ray
Get in here, Scoob. I'm only in the middle of a Jamaica story.
Lunchbox
Yeah, Teddy Bear, man. Teddy Bear.
Ray
Two spots. But then remember, there's mentions in the podcast, too.
Lunchbox
Got it.
Ray
I don't know what you're doing now, but maybe.
Lunchbox
Oh, yeah, yeah, we'll talk about that. Man. This, this. We're in Jamaica, man. They won't be able to make it to demolition derby.
Ray
Anyone seen Jamal, brother?
Lunchbox
Yeah, demolition derby. You know, we're the week of 223. All right, we got it. It's going to be in Shelbyville, Tennessee. Tennessee, March 8th at Cooper Steel Arena. Come see me. If you're in Jamaica right now, you're not going to be able to get there. But, hey, come on, let's do it.
Ray
So are we taking a break or. I can, I can roll real quick.
Lunchbox
No, you can roll real quick.
Ray
So the final pool day. I mean, Teddy Bear has been there for everything. I would say, shy of being in the bedroom with us for naughty time, he has seen us do everything. He has been on every pool chair with us. He's been on every inflatable. We'll be actually in the water, and he's hanging over the edge. Teddy Bear was a threesome. We were a throuple with Teddy Bear the entire trap. Oh, come to the last day. Why is Teddy Bear being so nice to us? Why?
Lunchbox
Because the big tip. I, I, that that's one of them.
Ray
But then also, and that's obviously not the answer. I knew you wouldn't know it.
Lunchbox
No, no, I, I know that.
Ray
Why is he being so nice to us? It's not the money.
Lunchbox
No, I know.
Ray
Tricked you. That's how a good host tricks you. That was really not because of money.
Lunchbox
This is a good crime pocket. It's like a plot twist. And so I'm gonna say he was really nice to you because he thought you liked a clock.
Ray
No. Incorrect answer.
Lunchbox
Oh.
Ray
So the final pool day. I'm severely hungover, but I'm still drinking. Naturally. It's a vacation.
Lunchbox
Got to.
Ray
And so they're bringing red stripe lights. We were doing these mudslides. Baser probably did a Bob Marley at one point. There was a blue drink that I told you about, the coral blue. We're mixing all these. I'm so hungover, I'm trying to check NFL scores. It was on Sunday. I mean, I'm shaking. I can barely pull up. Oh, Patriots are winning again. Okay, got.
Lunchbox
Oh.
Ray
Titans are down by 50. Got it. I can barely scroll my phone, much less do the request that Teddy Bear was about to come up with. Teddy Bear rolls over. Oh, man. So it's okay. Don't worry. You didn't come to any DJ set of mine over the last four days. It's okay.
Lunchbox
Even though I invite you on, man. I invite you this, I invite you that. You don't come to nothing, man. I thought we friends, man.
Ray
Every night at 11pm he had a DJ set. We never went once.
Lunchbox
Yeah.
Ray
Got invited 200 times.
Lunchbox
So you could have seen the next dead mouse. And you have no idea.
Ray
Teddy was on the wax of wax every night at the Whiskey Club, and it was always raging till two. I told Teddy we really, really don't stay out late. But Teddy, man, it's okay, man. Don't even worry about it, man. Hey, let me ask you this one favor, man. So if you go on, man, if you go on TripAdvisor, man, there, man, you can fill out, man, that I was good to you, man. You can say how Teddy Bear, man, at this resort, make sure you name the resort, man, was exceptional, man. Man, if you do this for me, man, you just. You just say Teddy Bearman Dunn's river, man. Then, man, that's how we get promotions, man. If we get enough TripAdvisor good comments and positive feedback, man. That's how you go level up, man. So you guys would help me level up, man. So he wants us to do these Yelp and TripAdvisor things. Ah, so aforementioned, bro. I'm shaking so bad, I. I couldn't even pull up X and be like, teddy Bear, send to the world. I'm shaking so bad. And so Baser, bless her soul, she has to, with decent wi fi, has to download TripAdvisor, she has to download Yelp, she has to download Google messenger, comment on trips, and. And she has to fill out 140 characters. So say you say Teddy Bear was comfortable and just a big old teddy bear. That's like 20. Baser had to write four paragraphs on every one of these apps for this. Dude. Sometimes she would run out, she'd be at 100, and she'd just do a bunch of emoji smiley faces. I go, bazer, bless your soul, because I can't even function right now to get on my phone right now in this tropical paradise, because I'm recovering. Okay, I'm actually going to give up drinking because holy crap, the effects are brutal. But Baser, for an hour and a half, probably at the pool on our final day, Teddy Bear is on our lily pad. And our pool bed that we paid $150 for camped out the entire afternoon waiting for Bazer to do all these comments on all these different apps and stuff.
Lunchbox
Oh, my gosh.
Ray
So that could be the end of the story.
Lunchbox
Oh, I thought that was it. I thought, okay, he's got proof. He's going to leave you alone.
Ray
The end of the story really is, don't ever tip these people when they say not to tip, because, holy crap, that got annoying talking to Teddy Bear every single day, time of the day. If, regardless of where the sun was in the sky, Teddy bear was 20ft away from us. And did she do them a favor? Yes. They can also get in trouble for it at these resorts. And she snuck the bartender 20. So hopefully that espresso bartender never got fired. Hopefully, Teddy Bear never got fired. And. And that's the lesson there. But there is that. All that to say this. I think Teddy Bear actually did get fired because so Baser filled out all that stuff, did all the comments, whatever. We did the stuff for him, and then we finally got rid of him. Well, he comes over and he gives me a shot glass. It says Jamaica on it.
Lunchbox
Yeah. And it said, teddy Bear's last day.
Ray
I go, thank you, Teddy Bear. Thank you so much. This is no lie. This is a dead God's honest, true story. I take this shot glass and we wanted to go play bingo. Why not do a poolside bingo?
Lunchbox
Why not?
Ray
We go over there. You couldn't. The universe couldn't have written this up any better. The host of Bingo. What is his name?
Lunchbox
Teddy Bear.
Ray
The host of bingo. His name is Ray.
Lunchbox
Oh.
Ray
And so when we all introduce each other, who do you think he's gonna know and look at and be the most memorable?
Lunchbox
Ray.
Ray
The guy that has the same name as him. Ray.
Lunchbox
Correct.
Ray
So the entire time he's saying, ray this, Ray that. Oh, Ray, how are you doing, Ray? Well, I took the shot glass that Teddy Bear had given. Slash stolen. And he goes, ray, how did you get that shot glass? We haven't even played the game yet. And I go, I got it from Teddy Bear. Teddy Bear came over and we were, like, helping him out, and he's like, here you go. Here's a free shot glass.
Lunchbox
No.
Ray
The only reason he gave a crap about me is because my name was Ray in this universe where the host name's Ray. And Teddy Bear stole a shot glass and. And gave it to me. It was the same shot glass that they gave at bingo if you won. I learned that five minutes later when I won and I said bingo. And Ray comes over and hands me the same shot glass that Teddy Bear had already stolen for me. And it was then confirmed that Teddy Bear stole a shot glass to thank us for all the reviews. But that stolen shot glass may have sealed his fate. So I don't know if Teddy Bear got the promotion and leveled up or if Teddy Bear got fired. And I will hang up and listen. Wow.
Lunchbox
That is a story from Jamaica.
Ray
That Jamaica shot glass, hot stolen piece of merchandise is sitting on our table in Nashville, Tennessee, right now.
Lunchbox
That's. That's beautiful, dude. That was great storytelling. That was worth the wait. And we'll take a break. What's the time?
Ray
3,000, 208,
Lunchbox
man. Do you have any more. Do you have one more story from Jamaica?
Ray
Told you about the tree when we landed.
Lunchbox
Yeah, you told us about the.
Ray
Yeah, I could. I could say that.
Lunchbox
The. How you got a strike on the catamaran. You told that at the live pod.
Ray
Well, then, no, the tree. I can tell you about the tree just because I had alluded to it earlier.
Lunchbox
Thank you.
Ray
So we had the tree that we had got five minutes off, again off a Jamaica plane, because Bazer had hurt seeing on the movies about this tree. So we got a Jamaican tree.
Lunchbox
Got it.
Ray
Okay. So we got the Jamaican tree. And I'm telling you, they brought me an entire bushel that I could put in the front of my house. It was that much. And I go, bazer, I'm not particularly fond of tree. I probably won't even touch the tree. I know you'll touch the tree, like, one time just to say that you did so that I'm carrying this absolute bush shrub that most people would put in front of their house, and I'm just having to lug it around Jamaica. It was that much, huh? It wasn't a leaf, it wasn't a stem. It was an absolute hedge that you see at the Georgia Stadium between the hedges.
Lunchbox
Oh, yeah, I know those.
Ray
And so what do you know? We bring it to our hotel room and we're hiding this tree because it's so big. And then why, why? Why don't we just throw it in the trash?
Lunchbox
You ask, why don't you just throw in the trash?
Ray
Why? I. Dude, I'm the most paranoid person you know. I would never want to risk getting caught and throwing this tree in the trash. So every single morning and night, we're shifting the tree. Sometimes we put it in here. Sometimes we wonder, does that tree smell weird? Maybe we should put on the patio. I'll put the tree on the patio for a second. So the tree shifted from the patio to one of my bags to that tree is just too much in my backpack. I don't want it in there. To. The tree went to a suitcase. The tree went to a drawer. What if we just go to a trash can and put the tree in downstairs? There's cameras. Why would I. I'm not doing that. I'm paranoid. I'm not going to go put the tree in a trash. I'm not putting it in my own trash, man.
Lunchbox
You're in Jamaica.
Ray
So the final day comes and we still have this freaking tree. That baser. Out of an entire beautiful evergreen, she had one pine needle of.
Lunchbox
Got it.
Ray
Thanks. Bays are glad we paid a hundred dollars for a tree that we didn't even use to shade us. But for five minutes. And so the very final day, I just left the tree in our trash can in our room.
Lunchbox
And we're nervous the whole time.
Ray
Well, and the reason we had to wait until March 8th is because I had to wait and see if we were gonna get seized or in trouble or get fined by the hotel. We got all our money back. We never got in trouble. All is good. So now I can tell the story March 8 about the tree that we had in our room. That's why we had to wait till March 8th.
Lunchbox
Wow.
Ray
The. The government, the local city policies, they never came down on us. They may have saw the tree in the trash, knew that we were americanos. They didn't care. They forgave. They threw away the tree. All is good.
Lunchbox
I gotta be Honest. I literally thought they love trees in Jamaica.
Ray
They do. But I don't think you can just outwardly have tree everywhere.
Lunchbox
I just assumed that Jamaica was a tree friendly environment. And I. I mean, that's just me maybe being ignorant. I have no idea. But I just. Oh, man. Reggae, man. I thought that was the whole culture of Jamaica. I don't know anything about Jamaica, though.
Ray
Hopefully I told you enough. So now you do know something about it. One more piece of advice.
Lunchbox
Yeah, please.
Ray
There was these. The Jamaican rum.
Lunchbox
How was it?
Ray
Well, we. I drank it over ice one night and it was God awful. I'm not a rum drinker, but we met these dudes from Chicago. They were very good friends.
Lunchbox
Got it.
Ray
And they said the rum was amazing. That to the point that every. I may have told this already that every day they would hide their rum bottles. Every. You would get a 8 ounce rum bottle in your room after the cleaning staff came through. Every day.
Lunchbox
Really?
Ray
So they would hide the eight ounce bottle and they would smuggle back eight, eight ounce bottles back to Chicago because you can't buy rum there or something.
Lunchbox
It's just a different type of rum. It tastes better. Maybe fresh from the tree of Jamaica.
Ray
It's God awful. So the rum ain't worth smuggling back. The tree is just too branchy. It ain't worth smuggling back. So if you went in our room on the final day, there was a trash can full of tree. Tree and half drank rum. But it ain't worth bringing back. So.
Lunchbox
Yeah, man. So do you still talk to your friends from Chicago?
Ray
No.
Lunchbox
They were really good friends.
Ray
The mom actually almost looked like Nancy Guthrie.
Lunchbox
Oh.
Ray
And so she was really sweet. And Baser was friends with her. And so their final breakfast. I hate that the story includes me being hungover again, but I'm eating breakfast. And Baser goes, how were you guys? How are you? How was Dunn's River Falls? That was good. Oh, my gosh. How did you guys like it last night? The performance? It was good. I didn't even barely talk to the two guys that were really good friends or best friends.
Lunchbox
Yeah.
Ray
And their mom. I bought her. I got her a diet Coke. And that was it. I had maybe two minutes of conversation with him. Baser act like it was our grandmother that she was talking to.
Lunchbox
Huh.
Ray
So there our goodbye was. Me at the breakfast table. Yeah. Great. Great meeting you guys. Enjoy Chicago. I don't care. I will never talk to you again. Have a good one.
Lunchbox
Yep. Okay.
Ray
They're there. They left smuggling 8 bottles of mini rum.
Lunchbox
Did you go BMW back to the airport. Did you go to the beach at all? Like, is the beach, like, right outside your thing?
Ray
Yeah, yeah.
Lunchbox
The.
Ray
The beach was. I'm talking footsteps. That's how we wanted it.
Lunchbox
Okay.
Ray
South Beach. It was almost South Beach. I would almost say 50 yards to the beach. Oh. Which was a little too annoying to go do it.
Lunchbox
Yeah.
Ray
This one I could throw. Like, Arnold could throw a football and hit the water from where our pool was.
Lunchbox
Okay. And he's got kind of a noodle
Ray
arm, so that's what I'm saying. But, yeah, it was right there. And no BMW. On the way back, we did a van with a bunch of other people, and they were very slow. So anytime we'd get off. Okay, guys. Hour and a half ride. We're at the bathroom for. We got 10 minutes here, guys. For eight of the minutes, I was waiting for the people with canes and wheelchairs to get off the bus. So that's probably why you do private transfer. Yeah, that's cool. But I'll just go to the bathroom for one minute. I can. Y' all pinch it. Yeah, no worries. No worries. You know what I'm saying? Joking a little bit. It'll cut off. I'll be back every time. And then when we got off, we get off at the airport. Oh, here you go. I mean, not like we were cutting it close, but we had it about an hour 45 until our flight. You know, usually paranoid.
Lunchbox
Oh, my gosh. Hour 45, dude, how are you doing it?
Ray
The guy goes, all right, we are here at the airport. You guys, thank you so much, man. Thank you for coming to Jamaica, man. Enjoy it, man. See you later, man. And we sit there, and nobody's in a rush to get off the bus. And where our seats are would be very rude to cut in front of everybody. So we just sit there, and they just slowly get up like they're at a dmv. I mean, they were in no hurry to live life. You got to respect it. But good gosh, do a private transfer, because, I mean, we're sitting there 10 minutes, then getting their bags. Holy crap. That process. I'm like, guys, give them a tip. Thank the guy drove the bus for 10 minutes.
Lunchbox
You don't.
Ray
Or an hour and a half. You don't need to talk. They're like, thank you so much. And then where was that that we passed through? Okay, guys, get your bag and get to the airport. The vacation's over.
Lunchbox
You're not gonna go visit that spot you just drove by? Because it's over.
Ray
Did the hurricane, when it came through, did it hit? They clipped a little bit. Oh, my. The guy lost his house and you're asking him about him like it's a tourist destination. Those houses that are half built, was that because of the hurricane? What I did notice is, dude, it's bizarre construction there. You would see 80% of the houses, they're half built mansions. So they either don't get the supplies or they run out of money. Run out of money, they just leave it. Half built, the entire drive. And then the shacks and shanties that you do see, they got the Jamaican flag up. Proud of their country.
Lunchbox
That's cool, man. Did you see where Bolt lived? Anybody talk about Bolt?
Ray
Yeah, I would bring him up and there was no language barrier. They spoke English and they didn't really talk about Bob Marley and they didn't really talk about Bolt. So there must be a new up and comer we don't know about in Jamaica.
Lunchbox
Sounds like good trip, man.
Ray
Teddy Bear, though, I. That's why I keep looking behind me, see if Teddy Bear's there.
Lunchbox
I give me nightmares, dude.
Ray
I started flinching around the second to last day. He was. Every time we come down to brunch, there's Teddy Bear. Hey, man, how was your sleep? How do you think it was, Teddy Bear? Just like any other sleep. I put my head on the pillow, pulled the covers over me and slept just like I have the port for previous nights. Teddy Bear.
Lunchbox
Oh, man.
Ray
You guys have a good brunch. What are you gonna do, man? Some eggs and bacon? Yes, Teddy Bear. We're American. We don't do any of the other stuff. We're gonna go strictly cut and dried. The same thing we've got in the four days previously. Ah, man. Have you tried, man, the orange juice machine, man, if you punch it down, man on Listen, Teddy Bear, we just do the minute maid. I don't need you to operate this orange juice machine. Even though it's pretty awesome. They crush the oranges in front of you.
Lunchbox
Oh, that's cool.
Ray
And it's straight from the orange, let me tell you.
Lunchbox
Fresh squeezed orange juice. Game changer.
Ray
That was actually one of the cooler things Teddy Bear showed us. Other than that. Hey, man, if you tried the plantain, man, it's. It'll. It's good mix. No, not Teddy Bear. Like I said on day one, all we do is eggs and bakey and a little wakey and then maybe some coffee and maybe a mimosa. That same thing. We've done the Last four days, Teddy Bear. Thank you, Teddy Bear. Thank you, Teddy Bear. Oh, man. I'll see you guys later, man. I'm still looking behind him. See if Teddy Bear's back there. Dude, I swear to God, during the convention, I thought Teddy Bear was gonna come.
Lunchbox
That have been awesome if Bazer invited him. On the low. Down low.
Ray
Did I save a picture?
Lunchbox
Question. I got a question. Rate Jamaica. Would you go back out of 10? What are we talking? Jamaica is.
Ray
I go the same. Same exact resort. It was phenomenal. It was. It was tops right now because the people are so freaking nice. The dive bar. Did they treat me bad? Yes. But, dude, they were actually so genuinely awesome.
Lunchbox
Okay.
Ray
And obviously, they. You know, they're kissing the ring. The one guy goes, dude, you must be cool as s back in America, right? And I'm like, yeah, yeah. He's like, dude, you're freaking hilarious, man.
Lunchbox
You know, talking about.
Ray
And they're like. And then, like, your chick back in America, she's like, the hottest. I'm like, yeah. She's like supermodel. See, they believe whatever you tell them. I'm like, yeah, yeah. I'm on a radio show. Oh, you host it? I'm like, they'll never hear it. Yeah, I'm the host of it.
Lunchbox
That's legit.
Ray
They thought it was the host of a radio show. And my wife was a Victoria's Secret model.
Lunchbox
I'm gonna text my wife right now, say, hey, let's. Let's hit. Let's hit Jamaica.
Ray
Where are we at, dude?
Lunchbox
That's good, man. Hey, dude.
Ray
What the heck have I been doing, bro?
Lunchbox
I don't know. I think that was a great pod, dude. I think you can wrap it. You can hit the button. I don't know what. They're not going to see the picture right now. We'll just post it on socials if we have it. If we don't, we don't.
Ray
The driver.
Lunchbox
Oh, man. That's our driver.
Ray
I don't know if I got Teddy Bear, though.
Lunchbox
Oh, Bazer's got a picture of Teddy Bear.
Ray
You would have. I wanted to play a Saudi. You would have. Just music.
Lunchbox
Oh, dude, that's beautiful. Oh, no, no. Let me see it. Keep going.
Ray
He was doing 50 Cent. I'm a pimp. I'm on the street, and I'm grinding on that butt. But he would play the sax to it.
Lunchbox
I love it, dude. Look at that, dude. You're not lying. You're right on the beach.
Ray
Yeah, we were right there.
Lunchbox
That's nice.
Ray
I Can post a couple of these, then. Here's my people. Teddy bear is not in this, but these are the bros there.
Lunchbox
Oh, they're having a good time.
Ray
We're chilling in the little villa we had the little day bed. Look, I'm smiling their butts off.
Lunchbox
Oh, they're. They're. They're on cloud nine, dude.
Ray
They love life. I mean, we gave greased them all,
Lunchbox
so when you're not supposed to. Let's get out of here. Just stop it, man. That's great.
Ray
There you go. They're pride in your country.
Lunchbox
Oh, they got Jamaica flags everywhere, dude.
Ray
That's pride in your country. This guy had two on his shanty.
Lunchbox
That's legit. How many?
Ray
He's got one in the door.
Lunchbox
Yeah, he does. How many American flags you got at the house?
Ray
We got one. If it was up to baser, we'd have about five more.
Lunchbox
Okay. All right. I'm U.S. transportation Secretary Sean Duffy.
Ray
The sound of a seatbelt.
Lunchbox
It's one of the most important sounds in our car. It means everyone is ready and everyone is safe.
Ray
The more our kids see us put
Lunchbox
on our seatbelts, the more natural it is for them to put theirs on, too. Make it a priority. Buckle up every time. Hear the sound. Make it a habit. Paid for by nhtsa.
Ray
You know how it's never really about where you're going? It's about who you're going with. The right people can turn any drive into a great memory. That's something Toyota really believes. They design vehicles around real life and real people, the ones who make plans happen and bring everyone together inside. Everything's built with passengers in mind. Comfortable seating, smart layouts, and space that actually works so everyone can relax and enjoy the ride. There's room for the people, room for the stuff, and room for the moments that happen along the way. Because when people are the destination, your ride is important. Learn more@toyota.com and find the vehicle that fits your people.
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T Mobile has the best plan on the best network. Just ask Kevin Bacon.
Ray
Today, business happens virtually everywhere. That's why you need Super Mobile from T Mobile. The best plan on the best network. Letting you run your business from your
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Lunchbox
Friends like these the Murder of Skyler
Ray
Nese is now streaming on Hulu and Hulu on Disney +911. Do you have an emergency? I have a 16 year old daughter. Can't get a hold of her. I am scared to death.
Lunchbox
We wanted to talk to Skylar's friends. They're not telling the full story.
Ray
The truth is gruesomely horrific. How could you do this to your best friend?
Lunchbox
There's a darker secret that's not been said.
Ray
Watch the new Hulu original series Friends
Lunchbox
like these, the Murder of Skyler Nese
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on Hulu and Hulu on Disney plus
Lunchbox
for bundle subscribers terms apply.
Ray
This is an I heart podcast.
Lunchbox
Guaranteed human.
Date: March 6, 2026
Host: Premiere Networks
Main Speakers: Ray, Lunchbox
In this episode, Ray and Lunchbox from the Sore Losers podcast detail Ray's recent vacation to Jamaica in a meandering, comedic storytelling session. The episode hilariously covers everything from frantic last-minute packing, airport mishaps, travel delays, and the VIP experience, to the colorful cast of characters encountered in Jamaica—most notably, an unforgettable resort staff member named "Teddy Bear." Between the travel fiascos, resort shenanigans, tipping misadventures, and navigating local “trees” and rum, the duo presents a vivid, relatable account of international travel for Americans.
Packing Habits:
"Me, I panic pack, and I pack, like, an hour before my flight." – Lunchbox [04:15]
"I'm doing laundry at 2am in the morning if we're leaving at 5." – Ray [05:54]
Airport Parking – Lessons in ‘Living Large’:
"Once you give a street cat satin sheets, they never go back to the street." – Ray [06:44]
"He said, 'Oh, sir, you have to wait in line.' … I said, 'Alright, I'll just leave the car, the keys on the seat.'" – Lunchbox [09:10]
Travel Delay:
"We hit a bird, we had to return back to Orlando or Miami or Fort Lauderdale. One of the three, don't know, had about three times that many drinks..." – Ray [10:32]
Interesting Plane Encounter:
"He was a recovering alcoholic. I said, I’m in recovery, too. Gambling addict. And he goes, here’s my drink tickets." – Ray [11:34]
First Impressions:
"This dude was talking my ear off ... Gotta go to Negril. ... Well, we’re actually going to Ocho Rio, so we're not even going to Negril." – Ray [13:12]
VIP Transfer:
"You could have paid, I want to say $100 for a bus with 20 other sweaty Americans now. Or $150 for a VIP ... happened to be a BMW car. I’ll do that." – Ray [14:08]
"I’m so sorry you have to drive us, Laura. Bazer, it’s his job ... I'm sure we tipped the dude $40 after we had already paid him like $150." – Ray [14:32]
First Brush with Locals (and Weed):
Their driver makes a stop to procure a massive amount of “tree” (marijuana), more than they could possibly use.
"He stopped just for a minute, comes back with an entire shrub. We’re never going to burn through all that. Maybe all we need is a leaf, you know what I mean?" – Ray [15:45]
Initial interactions with Jamaicans outside the resort are cold and unwelcoming.
"There’s 10 people at the bar looking at me like, ‘We hate American.’" – Ray [18:27]
Resort Welcome:
"It’s beautiful. The Christmas lights. There’s presents. Christmas trees lining the row. ... They made us feel like it was a Tropical Christmas, the minute we were there." – Ray [20:15]
Meeting Teddy Bear:
"Out of the corner comes this guy, Teddy Bear. ‘Mon, I’ll show you where Espresso Martinis are, man.’” – Ray [21:53]
"Me and Bazer combined have probably put enough drinks down to float a boat ... She slips the bartender $40 ... between $100 and $150, we tip Teddy Bear." – Ray [24:07]
Constant Companion:
"Over the next four days... Teddy Bear was a threesome. We were a throuple with Teddy Bear the entire trip." – Ray [27:24]
TripAdvisor Ordeal:
"'If you go on TripAdvisor … you can fill out, man, that I was good to you... That's how we get promotions, man.'" – Ray [29:15]
"For an hour and a half ... Teddy Bear is on our lily pad and our pool bed that we paid $150 for, camped out, waiting for Bazer to do all these comments..." – Ray [31:28]
"The host of bingo, his name is Ray ... and he goes, 'Ray, how did you get that shot glass? We haven't even played the game yet.' ... It was the same shot glass that they gave at bingo if you won." – Ray [32:44]
Fate of Teddy Bear:
"That stolen shot glass may have sealed his fate. So I don't know if Teddy Bear got the promotion and leveled up or if Teddy Bear got fired." – Ray [33:20]
The ‘Tree’ Dilemma:
"Why don’t we just throw it in the trash? ... So the very final day, I just left the tree in our trash can in our room." – Ray [36:43]
Jamaican Rum:
"The rum ain't worth smuggling back. The tree is just too branchy. ... A trash can full of tree and half-drank rum." – Ray [38:42]
Jamaica Reflections:
"You would see 80% of the houses, they're half built mansions ... and then the shacks and shanties ... they got the Jamaican flag up. Proud of their country." – Ray [42:52]
“It was phenomenal. … Right now because the people are so freaking nice. The dive bar… did they treat me bad? Yes. But dude, they were actually so genuinely awesome.” – Ray [44:52]
"They thought I was the host of a radio show. And my wife was a Victoria's Secret model." – Ray [45:28]
On Panic Packing:
"My time management skills are not the best...when we're planning coaches conventions, I'm always like, yeah, I'm gonna get it done...and then hasn't really happened that way." – Lunchbox [04:22]
On Over-Tipping:
"If you ever met us when we're drunk, we're the nicest people in the world." – Ray [24:41]
On Teddy Bear's Persistence:
“He has been on every pool chair with us. He’s been on every inflatable…Teddy Bear was a threesome. We were a throuple with Teddy Bear the entire trip.” – Ray [27:24]
On Online Reviews Motivation:
"'That’s how we get promotions, man...You guys would help me level up, man.'" – Teddy Bear (via Ray) [29:15]
On the Dangers of Overtipping:
"The end of the story really is, don't ever tip these people when they say not to tip, because, holy crap, that got annoying talking to Teddy Bear every single day..." – Ray [31:37]
The conversational tone is fast, irreverent, and full of inside jokes. Ray’s self-deprecating narration and Lunchbox’s prodding keep the pace light and hilarious. The episode blends travel insights, cautionary tales (especially about over-tipping and paranoia with contraband), and a tongue-in-cheek look at American tourists abroad.
If you've never heard this show before, this episode is an approachable, laugh-out-loud entry point—packed with relatable travel mishaps, quirky characters (especially the now-legendary Teddy Bear), and sage advice for vacationers: