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June 3, 2026 • 21 mins

Trips regretted. 

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Speaker 1 (00:00):
Would you say you're one of the ninety seven percent
of travelers who regrets a trip that you took once? Yeah,
oh Jesus, I'm sorry. Why do you regret? What trip
do you regret taking?

Speaker 2 (00:16):
So we went to a destination wedding in Puerto Rico
New Year's Eve and it was nowhere near any other
city town out in the middle of nowhere, and apparently
Newyear's Eve is a huge thing there. So at midnight,
people were driving around the hills shooting off machine guns.

(00:39):
It was terrifying. We did not know to expect that,
and like we all had to like stay low inside
the building so we wouldn't get hit by stray bullets.
It was looking back hilarious. Probably wouldn't do it again.

Speaker 3 (00:54):
Well, you can take.

Speaker 1 (00:55):
The word probably out of there. Oh my god, when
you were so quick to say yes, Like, I know
this is coming in my head. I can't think of
a trip that I regret. I mean, there's definitely been
trips that I've been on that haven't been as much
fun as I wanted them to be. But I don't
regret going. I don't think there's regret. Man, that's a

(01:16):
good one. That's a good one that's a really good one.

Speaker 2 (01:19):
Love the bride peerly would not have skipped her wedding
if she's listening, But going back there probably won't do that.

Speaker 4 (01:27):
Good for you, Good for you, So ninety seven percent
as I can look back on a bad trip.

Speaker 5 (01:34):
But does hers get chalked up to lack of research
because that was gonna happen regardless.

Speaker 3 (01:43):
Yeah, whether that wedding was taking place.

Speaker 5 (01:45):
She was the victim of a crime that involved guns
or whatever.

Speaker 3 (01:49):
Right, that just kind of happened.

Speaker 5 (01:51):
It's something that's done in a celebratory manner. So does
she regret the trip because she didn't put enough forethought
into it.

Speaker 1 (02:00):
Or does she regret the trip because she would like,
if you're the bride and groom, you should probably know
on New Year's they fire off machine guns. Yes, they
definitely should have known, right, So maybe that should have
been communicated to.

Speaker 5 (02:14):
Them, because if somebody said, well I regret going to
this destination wedding because the couple eventually divorced, I don's
gona on trip out of it.

Speaker 3 (02:24):
I don't regret going to Ballard's wedding.

Speaker 1 (02:27):
I didn't need examples, no, no, but that was a
de and we knew as it was taking place it
wasn't gonna last.

Speaker 5 (02:33):
So for these nearly one hundred percent of people, were
they given a definition of regret.

Speaker 1 (02:39):
No, but now there is a running theme that pops up,
like they they will say, for example, research shows illness
that breaks out, that you get fair, but you can't
help if you get sick. Yeah, remember the but you
don't regret. No, but maybe maybe if it's you cause

(03:02):
yourself to get sick. Like they said, don't eat the salads,
but I'm eating the salads.

Speaker 5 (03:09):
Salad.

Speaker 1 (03:09):
Please, No, don't they say that Mexico don't eat salad.
They say don't drink water. I always just say don't
go for people get mad at themselves not planning properly.

Speaker 5 (03:23):
That I could definitely be.

Speaker 6 (03:24):
Because do you feel like you're wasting us.

Speaker 3 (03:26):
Setting an unrealistic budget?

Speaker 5 (03:29):
Sure? I get that one too.

Speaker 3 (03:31):
Traveling with the wrong companions.

Speaker 5 (03:34):
But is that like we broke up after the trip.

Speaker 7 (03:36):
No?

Speaker 1 (03:37):
No, I don't think it means boyfriend girlfriend of like, hey,
we're going with friends and you get there and you're like,
oh my god, why did we agree to go someplace
with these people?

Speaker 3 (03:46):
Okay, they're fun to live in the neighborhood with but
Jesus age Christ.

Speaker 1 (03:51):
And then the other one was like you just you
let stress take over and you just don't allow yourself
to enjoy it, like you get too stressed out.

Speaker 3 (03:59):
But why would you regret the trip?

Speaker 5 (04:01):
I know that you're struggling to figure out one for yourself,
but I know one for you.

Speaker 3 (04:07):
Miami.

Speaker 5 (04:09):
No, what was that trip?

Speaker 3 (04:10):
Oh? That was the only one I could think of too.

Speaker 4 (04:12):
Where were you just connecting out of Miami or were
you just no?

Speaker 1 (04:16):
No, this is this goes back to why I had
such a love hate with Miami. Is that we went
We went on a trip to Jackie and I went
on a trip to Miami. We actually went with friends
who great friends. It wasn't a companion issue. But we
got to Miami and I was like whoa, whoa. I
was not expecting this, Like this was like some something
was going on, and we ended up we ended up

(04:37):
leaving not not Miami, but just where we were.

Speaker 5 (04:40):
So you let others do the planning. You didn't do
any sort of itinerary.

Speaker 2 (04:44):
Yeah.

Speaker 1 (04:44):
I wasn't planned, I wasn't prepared, but I had a
great time. Once we once we switched hotels, it was great.

Speaker 3 (04:51):
It was great.

Speaker 5 (04:53):
Oh so yeah, that's not so I don't regret it.
Now I'm thinking of a show trip and without getting
into the details, I know you hated when we were
in Portland, Maine.

Speaker 3 (05:02):
Oh, but I don't regret that trip.

Speaker 4 (05:05):
There was no planning, no circumstances. I made him hate that, Yes.

Speaker 3 (05:10):
And I knew going into it. I was good, But not.

Speaker 5 (05:12):
That you didn't know?

Speaker 3 (05:14):
You didn't is that when it got worse, it definitely
was bad.

Speaker 5 (05:18):
That trip was the tipping point.

Speaker 1 (05:21):
Yeah, but did did? I I would have never known that.
I know exactly what you're talking about.

Speaker 5 (05:26):
And I don't want to get into it. But that's
a trip I honestly think you But I don't regret.

Speaker 3 (05:30):
It, No, because I loved like I loved going to.

Speaker 6 (05:34):
Portland, fun in the city.

Speaker 5 (05:35):
Yeah, you were miserable.

Speaker 3 (05:41):
Except when I was asleep. That was it. That was it. Yeah, No,
that that's fair. That's fair. Okay, So you'll count that
I regret my trip to Portland.

Speaker 5 (05:52):
I hope that's the only show trip that maybe you
had those feelings about.

Speaker 1 (05:55):
Oh, because like even when we met, I'm so angry,
Like when we met, all the listeners on the boat
that was at the well, yeah, but not if you
live in my brain. I was like, can I just like,
let's let's let's lighten this boat load.

Speaker 5 (06:08):
You kept asking me if you could fly home early.
That sounds like a real fun trip.

Speaker 3 (06:16):
Okay, that's fair, that's fair. I'll give you that one.

Speaker 5 (06:18):
But is that like for show trips I'm talking about
not just with this show, because are these people talking
about pleasure only or is there some professional.

Speaker 1 (06:31):
They don't they don't, they don't break it. I just
read it as personal or pleasure and not work.

Speaker 5 (06:39):
Yeah, I think it's more fun to take it that way.

Speaker 3 (06:41):
Ye to hear.

Speaker 1 (06:43):
Because people have gone on workshops have been like the company.

Speaker 3 (06:48):
But personal, No, I can't other can't you have name two?

Speaker 4 (06:53):
Now?

Speaker 1 (06:53):
The no on ones work the and but the Miami
one turned out to be fine, But it did he
give me a bad opinion of Miami for a while.

Speaker 4 (07:02):
We always said that this when when Marley was younger,
she's probably like four, we went to like beaches, the
all inclusive family and Turks and Caicos horrible, really expensive, right,
but you know that going in it was one of
those places where you got to get up at five
to put a magazine down so you can get a

(07:23):
beach chair.

Speaker 5 (07:24):
Screw that.

Speaker 4 (07:24):
On vacation, the I mean the and the the draw
of that was they have like all like the Sesame
Street characters running around, and it's all it's a family thing,
it's it's all for the kids.

Speaker 6 (07:36):
She was terrified of them because they're all like six
feet tall.

Speaker 8 (07:39):
L noo.

Speaker 1 (07:40):
And also, if I had to, if I had to guess,
you know who, I bet did not love all the
costume characters running around and singing and dancing.

Speaker 6 (07:47):
Scott, we made it. We made it the best we could.
The food sucked, it was horrible.

Speaker 3 (07:53):
So you hated everything.

Speaker 6 (07:55):
I mean, we just getting we muddled through.

Speaker 4 (07:58):
But I was just thinking like, well, great, this is
the one time I get to go away this year.

Speaker 5 (08:03):
Often perfect. So you were angry at Elliott the whole time. No,
I didn't say it goes on my fault.

Speaker 6 (08:12):
It just sucks because you know, I mean, vacation time.

Speaker 4 (08:14):
You exactly right, and it's not and it's and it's
not an everyday thing.

Speaker 6 (08:19):
And so when you screw up, man.

Speaker 3 (08:22):
Yeah, that's not on me. That's not on me.

Speaker 4 (08:24):
I was one and I was just like we were
trying to do the right thing. Let's make it a
fun thing for the family. Like, no, screw that, never
go back there again. And like the food, Like I
remember eating biting into a piece of broccoli and it
tasted like soap. It was like, what did you cook
this in the dishwasher?

Speaker 5 (08:42):
Disgusting?

Speaker 6 (08:45):
Worst vacation ever?

Speaker 3 (08:51):
Hi Elliott in the morning, Hey this, Yeah, you regret
a trip?

Speaker 2 (08:56):
I do?

Speaker 9 (08:57):
I have fun where a whole bunch of stuff went wrong?

Speaker 3 (09:01):
Well? Where did you go?

Speaker 7 (09:03):
So?

Speaker 9 (09:04):
I was visiting my family in California. We live out
in fall Church, and my youngest daughter at the time
was turning. She was a little over one, and we
figured we should go and visit my grandma. She's in
her nineties. She's not really traveling anymore. So I figured
we take her out there to meet Grandma and we
have a whole family get together. My grandma ends up

(09:25):
falling and hitting her head on the concrete at the
airbnb we were staying. I had to get the police,
The fire truck came out and everything took her to
the hospital. She ended up generally being okay. That was
like the first night of the trip. Second night, we
go out to a Mexican place. My wife gets food poisoning.
She's up all night throwing up. I stupidly did not

(09:48):
think it was the restaurant that we went to. I
gave her, I gave the restaurant the benefit of the doubt.
I ate her leftovers. The next day I got food poisoning.
So two back back food poisoning. We went said Disneyland
one of those days while my wife had food poisoning.
She's slogging around carrying a one year old and ninety
degree heat through Disneyland, trying to act all cheerful, having

(10:09):
a horrible time. And then my daughter was also on
antibiotics for some ear infection she had or something at
the time. She ends up having an allergic reaction towards
the end of our trip. We go to the hospital
on our flight home. On our flight home, she's so
swollen it looked like she had gone nine rounds of
Mike Tyson. Her face is all bruised up and eyes
are almost shut, and everyone's looking at us like we're

(10:31):
terrible parents. It was a horrible trip.

Speaker 3 (10:34):
Yeah that's bad.

Speaker 8 (10:36):
Oh my god. Yeah, all right, very good, thank you, sir,
thank you. So he obviously had a lot happened the trip.
But I bet thinking your kids are old enough to
do something is a massive Oh yeah, that's people.

Speaker 5 (10:50):
Now he brought up Disney. I'm not just talking about
amusement parks, but thinking that they are the age that
they can handle something and they end up not being Yeah, I.

Speaker 1 (11:00):
Think that whenever you hear somebody is like, oh, like
we will hear from like, uh listeners, Oh we're going
to Spain.

Speaker 3 (11:07):
We're taking our four year old?

Speaker 1 (11:09):
Why, I don't care the no and they're bitching and
they can't.

Speaker 6 (11:13):
They can't get on the schedule, wrapping.

Speaker 1 (11:15):
Their pants, they don't want to eat like that always
seems wasteful.

Speaker 5 (11:20):
Ira, Right, So what about the guy who went to
Columbia on this sort of blind date that we never
heard from Again, that does go back, yep, but we
don't know. Maybe he stayed down there and lived heavily.

Speaker 1 (11:36):
He could be he'd be living with a with a
family of Colombians and happier than a pig and ass.

Speaker 3 (11:43):
Hi elliot in the morning. Yeah, Hi, who's this? Yes, sir?
What can I do for you?

Speaker 10 (11:53):
I did a little barton and back in the day,
and uh, liquor up. I want a competition, got a
freeze trip to the Bahamas from them, all paid all inclusive.
The day that I ended up being told to go
down there, it was election day, so everything was closed
and that illegal to sell alcohol.

Speaker 3 (12:09):
Dude, that sucks. That sucks.

Speaker 1 (12:11):
Thanks, thanks, thanks for the trip. I heeart, that's what
our company would do. Wow, that I get you. I
would regret that ninety seven percent. That seems high.

Speaker 6 (12:28):
Everybody's got a bad vacation story.

Speaker 1 (12:30):
I know, but just because there was like one moment,
one moment, like I remember we went to Jackie and
I went to Montreal once because she wanted This is
when my dad's brother was still alive, and she was like,
I want to meet your dad's brother, like I want
to hear old stories and meet.

Speaker 3 (12:45):
Somebody, because Jackie never met my dad.

Speaker 1 (12:47):
And I was like, no, we're wasting time, like he's
half demented, like the bed stutter, like it's just it's
gonna be rough. And we got to lunch and the
three of us sat there like Jackie asked a billion
questions and he was like I don't know, I don't know,
and I was like waste I know, but I was like,
nothing's gonna come of this. The only bright spot was

(13:09):
the maple leafs were staying at the at a hotel
near Buying. A bunch of them came in for lunch.
So I sat there and was like, oh my god,
it's Eric Lindross. And then I had explained to my
uncle for nine times during lunch who Eric Lindross was?

Speaker 5 (13:24):
Do you count this? A few people have told stories
about leaving knowing a family member was not well, and
while they were away the worst happened.

Speaker 3 (13:39):
That's a great example.

Speaker 5 (13:41):
But I'd like, great examply somebody in these situations responding
to their stories saying, you can't blame the destination, like
you took it out.

Speaker 1 (13:51):
No, but I but I understand that that they would
regret going because in their head they probably were like, well.

Speaker 5 (14:00):
But it could have been anywhere.

Speaker 3 (14:01):
Grandma, Yeah you could have been at home.

Speaker 1 (14:03):
But what I mean but you but in your head,
you know Grandma's not really doing well. They just put
her in hospice, and uh, I'm getting ready to go.

Speaker 3 (14:11):
To Turks and Caicos.

Speaker 1 (14:13):
I got a great deal at uh at Beaches and
then you get there and.

Speaker 3 (14:17):
It's like, well, turn around and fly home.

Speaker 6 (14:19):
That's why you get.

Speaker 3 (14:23):
Yeah, I would count that.

Speaker 1 (14:24):
But it's not the destination's fault, but it's it's lack
of planning.

Speaker 5 (14:29):
Well, people, when they said planning in your article, I
think talked about like scheduling things.

Speaker 3 (14:35):
To Yes, no, that's true, but you kind of if
you know that's coming.

Speaker 1 (14:39):
Yeah, but if you didn't know, by the way, I mean,
finish the vacation.

Speaker 5 (14:46):
If you need to get back for a death, I
mean the vacation.

Speaker 3 (14:52):
When's the when? When of the services? You're Jewish? You
know that?

Speaker 6 (14:55):
Yeah?

Speaker 5 (14:55):
Pretty quick? Okay, Oh you would miss everything.

Speaker 3 (15:02):
I'm missing one tomorrow.

Speaker 5 (15:04):
We told you to go to that.

Speaker 3 (15:06):
Yeah, I'm not going. I oh, I know, I'm not going.
I'm not going.

Speaker 5 (15:11):
And has your mom finally come to terms with that?

Speaker 3 (15:15):
I mean she went?

Speaker 5 (15:17):
Is she talking to you?

Speaker 3 (15:18):
I haven't talked to her.

Speaker 5 (15:20):
I guess that's a bad barometer.

Speaker 3 (15:26):
Yeah. No, I got a link.

Speaker 1 (15:27):
If I want to watch the service tomorrow, will you
at least please it's well run.

Speaker 3 (15:32):
Well it's one hundred percent while we're on the air,
So no, I won't. Okay, Yeah, where am I going? Christmas?

Speaker 5 (15:39):
How I felt last Friday for the power to the
people pre sale, Why can't we get off at ten?

Speaker 3 (15:47):
Hi Elliott in the morning.

Speaker 11 (15:49):
Hey Elliott, Yes, sir, worst vacation ever. Now we stands
in Sandusky o Ion now permanently closed for bacteria in
the indoor pool.

Speaker 3 (16:01):
So wait, is that like?

Speaker 4 (16:02):
Is that like?

Speaker 3 (16:03):
No, that's what I was gonna say. Well, not ced
your point, but is that like Great Wolf Lodge?

Speaker 11 (16:09):
It's it's similar. It's like an indoor water park like
gl gotcha?

Speaker 1 (16:14):
Oh really yeah? And it's it was horrible the whole time.

Speaker 11 (16:18):
Well, so I got a mouthful of water into my
stomach and in the middle of the night it was
coming out both ends. Elliott.

Speaker 3 (16:30):
That's good, that's really good. Yes.

Speaker 5 (16:32):
Time from Instagram. Took a trip trip with my wife's
family to celebrate her grandmother's ninetieth birthday. She had late
stage Alzheimer's, and the whole time somebody would say things like,
let's take a picture, it might be our last with her. Nice,
or let's make sure it's grandma's favorite meal so we

(16:55):
can share it with her one last time.

Speaker 3 (16:58):
So enjoy mashed potatoes.

Speaker 5 (17:00):
No, no, it's not the nature of the food.

Speaker 6 (17:02):
No, it's just everything with utterance.

Speaker 5 (17:04):
This could be the last.

Speaker 3 (17:05):
Time the rain on my.

Speaker 5 (17:08):
My god in all caps, they were right awful.

Speaker 3 (17:12):
Yeah, I can see that. You know what, Let's go
to a rave. It could be the last time Grandma's
that's horrible. Yeah, don't bring me down like that. I'm
on vacation, bro.

Speaker 5 (17:24):
And that's one of those things where they they knew
that was probably gonna be the last getaway with her.
So that's on that.

Speaker 6 (17:30):
There's there's a sadness around it already.

Speaker 5 (17:32):
They like they went into it thinking this this was
the last of something, and then everything became the last
of that.

Speaker 3 (17:40):
But that's no.

Speaker 1 (17:40):
But that's where you got it. You like, it can't
be a trip. It has to be like this may
be the last time. Like we sit on her couch
and watch Wheel of Fortune and then done.

Speaker 3 (17:55):
Hi Elliot in the morning.

Speaker 7 (17:59):
Yeah, Hi, Hey, this is Andrew calling from Arlington. How's
it going on?

Speaker 3 (18:04):
Elliott?

Speaker 4 (18:04):
Hey?

Speaker 3 (18:04):
Good? What can I do for you? Sir?

Speaker 4 (18:07):
Hey?

Speaker 7 (18:07):
Worst trip I ever had went to my brother's destination
wedding in Cancun, had several misconnections and almost missed the
uh the night before the wedding, but we end up
getting there super late. Parents are super pissed, and then
we go to this gathering they're having the night before,
where you know, people who haven't seen each other in
a long time go to and met up with each other. Right,

(18:30):
ended up playing this wedding game where you had to
pinch your nose, bend over, spin in place ten times,
kick your shoe in the air, and catch it and
then if you caught it, you would get like a
gift card or some other random gift. So first person goes,
spins around and falls down immediately. Right then they call
on me to do it, and so I start spinning

(18:51):
and I'm like, no, I'm gonna fall down immediately.

Speaker 11 (18:53):
This is terrible.

Speaker 7 (18:54):
So and what ends up happening is I end up falling. Anyways,
then when I come to when the world's up spinning,
I hear gasps, and I'm like, what's going on?

Speaker 4 (19:03):
You know?

Speaker 7 (19:03):
And then so I look and my dad is on
the floor and he's moaning and groaning. Turns out he
stuck his leg out to try to break my fall,
and I ended up breaking it.

Speaker 3 (19:16):
At the night of the wedding.

Speaker 6 (19:18):
Oh god.

Speaker 7 (19:20):
And it's it's just the story gets even worse, you know.
We go, we end up going to this hospital my
brother or my sister in law is made of honor.
It was like, you cannot get medical treatment here, just
get an air cast, go to the wedding and a
man out the next day. So we go to the wedding.
Everything goes as well as possible with my dad and
air cast in a wheelchair. Then we fly out the

(19:43):
next day and leave early, but my sister stays behind,
and so we get the dullest and then we take
an uber. This is when uber is relatively news. So
an uber from Dulles to Silver Spring was like one
hundred fifty dollars. Pants were super pissed. So we end
up getting home and then we're trying to get inside
and I looked at my parents. I said, all right,

(20:03):
give me the keys. We said, we don't have the keys.

Speaker 3 (20:05):
We thought you had the keys, that your sister has
them back at Mexico.

Speaker 7 (20:10):
Right exactly, she has the keys. I had to climb
my roof at the time of my parents' house, climb
the roof, try to open my window and got it open,
but broke the window in at Burton Lee got the
neighbors saw and called the cops, and that was the
whole or deal too.

Speaker 3 (20:27):
So Jesus, what a trip. By the way, that game, though,
that may not be bad.

Speaker 1 (20:32):
If I hit, if we hit a quiet moment in
our Q and A with Annie Columbia.

Speaker 3 (20:37):
Night, maybe I'd bring that game into the clubhouse. No, no, Annie,
hold your nose.

Speaker 1 (20:43):
Spin a little bit, and if you fall, I'll put
my leg out to go ahead and break your fall.

Speaker 3 (20:48):
That's a bad one. That's a bad one.

Speaker 5 (20:51):
I got one more for you. Go ahead, Elliott. Doesn't
everybody regret at least one spring break?

Speaker 3 (21:00):
I don't.

Speaker 5 (21:01):
And they go on to write from the sixteen hour
carpool drive down to the oversouled Piranha minded hotel that
made us wait for hours in the hallways, to the
drunk roommate that just lost her father and didn't know
she got her period and was bleeding everywhere, to the
twenty four to seven white T shirt contests outside her room,
and the guys banging on the door of the whole

(21:22):
week trying to get in for the other whoror roommate,
and the final roommate who was lost for twenty four hours.

Speaker 1 (21:29):
Oh that sucks. That sucks. That's a rough one. But
I bet you look back on it.

Speaker 3 (21:35):
And love it. Did you get the census. They regret it,
they regret it.

Speaker 5 (21:39):
They wrote million percent, regret this trip.
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