Brooke and Jeffrey: Second Date Update - Second Date Update: No Snow Show
Episode Date: February 2, 2026The woman on the phone today learned the HARD WAY after her date promised to give her a luxurious “experience of a lifetime” that she shouldn’t be so quick to trust. She’s read...y to call him out in a Second Date Update! See omnystudio.com/listener for privacy information.
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In the middle of the night, Saskia awoke in a haze.
Her husband, Mike, was on his laptop.
What was on his screen would change Saskia's life forever.
I said, I need you to tell me exactly what you're doing.
And immediately, the mask came off.
You're supposed to be safe.
That's your home.
That's your husband.
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Hey, it's Joel and Matt from How to Money.
If your New Year's resolution is to finally get your finances in shape, we've got your back.
Prices, they're still high and the economy is all over the place.
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Each January, men promise to get stronger, work harder, and fix what's broken?
But what if the real work isn't physical at all?
I sat down with psychologist Dr. Steve Poulter to unpack shame, anxiety, and the emotional pain men were never taught how to name.
Part of the way through the valley of despair is realizing this has happened,
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Oh man, this one gets wild.
Hey, it's fucking Jeffrey in the morning.
We got a brand new second date episode.
And I don't know.
I mean, I think that there will be
as many people on the woman's side
as there is the man's side on this one.
Really?
I don't know.
I tend to lean towards a guy here, but...
Yeah, that's true.
But then there is...
Yes, yes.
A lot of women might agree, for sure.
I don't know.
I don't know either.
Yeah, there's all kinds of people out there.
There is.
There is.
True.
Yeah.
Either way, you're going to have some feelings coming up.
And let us know them.
I just really imagine a bag flying in first class by itself,
buckled in, like on some flight.
They're just putting the food in the purse.
That'll make sense in a second, for sure.
All right, let's get to a listener.
What do we go?
Yes, Stormy Sky said, this is the type of calculated dating I never knew I needed to hear.
Oh, calculated.
I like that word.
Oh, that must be from the one where she made the rules for herself that we had last week.
Yes.
So now that you heard it, I don't know if this is going to make your dating life better or make you one of those people.
I don't know.
Well, maybe being one of those people makes things better.
I don't know either.
I definitely was not calculated in my dating life.
Very messy.
But it all worked out.
So good luck to everyone.
and here's your brand new episode right now.
Brooke and Jeffrey in the morning.
Second Date Update.
Today's second date update is going to be a little different.
Oh, okay.
Because one of our listeners, Kelly wrote in saying she is 100% not interested in getting another date with this guy.
Oh, we've done a couple like these.
Not very often, but every once in a while.
Why are we doing a second date then not like a awkward or something?
It's like a revenge call.
What answer?
Yeah.
I understand the confusion because it kind of goes against the whole point of.
this segment, but I'm giving her a pass
today because apparently
there is a juicy story that goes
along with it. And also
I'm a sucker for people who threaten me over
email. I will give in
pretty much immediately. Wow, she already threatened.
Why do I like her already?
Respect. Kelly, welcome to the show.
Hi guys. Hey, Kelly.
Oh, man, such a nice voice
for a threatening, scary woman.
I don't know. I've chills down my spine and just
hearing you in person now. And
And Kelly, I don't know the full situation that you're in right now, but apparently there is a dude that you went out with.
According to your email, you want us to call him today.
What's his name?
Calvin.
You said it.
What did he do wrong?
Can you just imagine with a name like Calvin?
No, we met on a new dating app that I was trying out.
Okay.
What is it?
Slightly risque and it has a financial bar.
For both sides or just for the men?
For both sides.
Okay.
Oh.
Okay.
It's rich people dating up.
Okay.
I have no idea.
I didn't, yeah.
We're not in the right tax bracket to know.
I literally can't picture what dating up this is still.
Like, I don't.
Yeah.
But I've always said the world needs more rich people marrying other rich people.
Yeah.
This lifestyle management, yes.
Yeah, we just clicked.
We talked back and forth all the time.
He just, he seemed very cool.
Okay.
I said exactly what I was looking for on paper.
Was there a date that happened between you two?
Yeah, well, we're not in the same location,
so you can match with anyone all over the world.
Oh, wow.
So are you at least in the same country?
We were both in the U.S., yeah.
We were in completely different places.
Temporarily, I was going to Dubai next week.
I know.
Alexis rolled her eyes at the idea of him being in the U.S.,
but that's okay.
Yeah, gross.
We have options all over the globe,
but I guess you want to slummit here?
I see you, girl.
So, wait, did you fly to him or did he fly to you?
It was actually quite sweet.
We were talking one afternoon and I said, you know, I used to love the snow growing up and I didn't get to see a lot of it where I lived.
So he lived somewhere that it's snowy in the winter.
And so he suggested a really nice resort in his area.
When you say a resort, what do you mean?
What type of resort?
Guy resort.
Okay.
It's a nice, like, five-star with a spa and locations.
That's a concierge.
Anseillaise that brings your skis to you
so that you can hit the slopes after your morning
brevet. So you're both good skiers?
No, it sounded great, but he, well, it's not
his fault. He didn't realize, but no, I don't. I don't ski.
But the bar at the lodges is fun, too. That's right. A prey all day.
A prey all day, okay. Yeah, I didn't mind if he skied.
So anyway, we get out there and
we'd agree that I would spend one night in his place
before we drove an hour away to the resort.
Okay.
Okay, wow.
All right.
We did that.
He offered me the guest bedroom, which was very gentlemanly.
Good.
Yeah.
He made a great first impression.
It was right on target.
Okay.
Yeah, it sounds awesome to be able to do this for somebody, too.
I know.
Now I'm, like, confused because your email said you're not interested in seeing him again.
Like, how did you reach that conclusion?
I'll explain.
So we get to the resort, and the resort, you know, it's nice enough, but there is zero snow.
Oh.
Oh, you're going to trigger Brooke.
Oh, geez.
I got to say, though.
It's not a very good season, right?
Like, at a lot of resorts.
Is that what was going on?
I have no idea.
I don't keep tabs on ski resorts because I don't ski.
And he does, so I assumed he would have, he could have called just to check.
I see.
You feel like he should have canceled the date or changed the plan after realizing there wouldn't be enough snow at the resort.
Right.
Or not suggested it.
I mean.
Oh, no.
I mean, I know your goal.
was to see snow, but maybe his goal was just to have a date weekend.
Yeah.
Well, then it starts to feel like, you know, he's just inviting me over for Netflix and
chill.
He'd made it such a big deal about it being Winter Wonderland.
He did promise you a lot and not deliver on any of it.
I mean, is this a reason why you're so upset?
Yeah.
I mean, he also had no plan to entertain us.
I mean, I had to kind of fend for myself.
I was like, oh, I guess I'll get a manny paddy and a massage.
That sounds awful.
Stuck in a lodge with only a spot.
on a hot.
They have to watch a movie or something.
Brooke, what are you not understanding?
He's a liar.
He manipulated her into thinking that they were going to have this magical winter experience
and then didn't do any of that.
I bet he was disappointed too, wasn't he?
Because he's a skier, so wasn't he disappointed?
No, he didn't seem bothered by any of it.
He was happy to just Netflix and chill, I think.
Oh, he's trying to turn, you know, lemons into lemonade.
So you've decided he is not a good guy.
You don't want to date him.
But what made you reach out to us?
Like, what are you hoping to get out of this call?
Well, this is why my friend told me to call.
So I left.
I just called an Uber finally because he just wasn't initiating any plans.
He just wanted to sit around all weekend.
And finally, I was like, okay, I think we've ridden this train as far as it's going to ride.
And I called a car and popped a flight out.
Well, my bag was still at his house.
What?
Oh.
I have contacted him several times and asked him to ship the bag back to me.
And he's not responding at all.
So my luggage is at his house.
I only had a small bag with me, like an overhaul.
So you went straight from the resort to the airport and flew home.
Did you tell him?
Did you tell him you were leaving?
Yeah, I left a note.
Oh, so he came back from like skiing or something and was like, oh, she's gone.
Not skiing because there's no snow.
Yeah, he was at the gym or something.
Selfish.
So we're just calling him to try to get your expensive bag back.
I just want my bag back.
Okay.
Okay.
We will actually follow through with our promises.
Unlike Calvin when we come back and do this call right after this.
Hold on.
Brooke and Jeffrey in the morning.
Second date update.
I just want to apologize to all of the women of this world for the low-life selfish men who lie and mislead them.
We are the worst.
Yes, because when a man plans a winter vacation, he should at least make sure winter is there.
Come on, man.
Hello, winter.
Where'd you go?
Okay.
But nope, despicable schmucks like Calvin exist, unfortunately.
Because he promised our listener, Kelly, a luxury resort weekend full of skiing and champagne and hot tubs.
She doesn't ski, but she did want to see the snow.
Yeah.
And he promised her that, but when they arrived, nope, not a drop of snow on the mountain.
Thankfully, we have somebody to blame for that.
Calvin.
Okay.
He controls the weather.
At least Kelly's blaming him for not checking.
That would have been the responsible, not selfish thing to do.
Guess you couldn't be bothered to do that.
So that brings us to where we are now.
Oh, and yes, she also left her bag back at Calvin's house, and she kind of needs that back.
She left in a hurry and just left him a note.
Who could blame her?
I would get out of there, too.
So that's our mission today.
Kelly, again, I am so, so sorry that you were having to go through this.
Thank you.
I appreciate the sympathy.
You are welcome.
Kelly, can I point devil's advocate for just a second?
What's her favorite thing to do?
We're against men right here.
Did you ever think that maybe you could have talked to him about how you felt?
What?
And spent two or three days expressing my displeasure with this situation.
I should have known you made it loud of clear.
Yeah.
I just feel like you didn't give him a chance.
Brooke, how many times on this show are you going to take the men's side?
It's annoying.
Constantly standing up for the male species.
The listeners are sick of it.
They're disgusted.
Have a woman's back for once.
Can you please?
Come on, Brooke.
I knew that was coming, Jeff.
Can we just call Calvin?
We're going to reach out to Calvin and get your bag back.
Kelly, are you ready?
I'm ready.
Thank you.
Let's do this.
We start the call in that tone, Jeff.
I'll bring it down.
I love when people can't sense sarcasm.
Hello?
Oh, Calvin.
This is Calvin, right?
Do not come in that.
Hot, Jeff.
I just said his name. Calvin?
No, you didn't just say it.
I said, oh, Calvin.
Hi, Calvin.
Hello?
Yeah.
Good morning.
Okay, just confirming.
Oh, Calvin, we're with a radio show called Brooke and Jeffrey in the morning.
Don't sound too excited.
You've probably heard of it.
No, no, I don't know what this is.
He's being so polite.
Yeah.
Look, Calvin, this is a segment that we do.
It's called the Second Date Update.
Normally, we're trying to, like, reconnect listeners after they
gone out with someone and they're not getting a call back.
We're on a kind of a different mission today because we heard from a girl that you met up
recently named Kelly.
Really?
You're joking me, right?
He's shocked.
What did you have to say to you?
Oh, she had a lot to say, Calvin.
I mean, spoiler alert, she's not happy.
She doesn't mince words.
No shit.
Oh, you got the sense that she wasn't having a good time on your quote-unquote ski trip?
Yeah, I got that sense over and over.
Oh, my God.
Oh, my God. What was it like?
Did she give up the vibes to you? She'd fake happy?
Are you calling me to hear my side of the story? Is that what this is?
Yeah. And an apology maybe, but go ahead. What's your side of the story?
Well, wait.
Sure, I mean, I'm curious what you know. But you know, it doesn't matter. Sure, here's the story.
She was really excited to see snow.
Yes.
So I said, I would love to take you to this resort, I know.
We heard that. Great. And yeah, okay. So you've heard all that.
we got there and there was hardly any snowed.
And how bad do you feel on a scale of 1 to 10 right now?
Right now? I don't feel badly at all.
Now, wow.
But did you at the time?
Sure, sure. Like I didn't take the time out to check the weather forecast or see what the snow conditions were.
And that's totally on me and I absolutely apologize for it.
But literally it was like taking a toddler of a candy shop and the candy shop is sold out of candy.
What?
Did she throw a fit?
She threw such a fit.
Oh, what?
And look, I'm the kind of person who, like, just wants to, you know, take the situation you have and make it as good a time as possible.
And that's not her.
She just kept wanting to complain and remind me, you know, help you not check.
Oh.
Like she was yelling at you?
Yeah, she's literally like, what are you going to do now is there's no snow?
And I'm like, it's still the beautiful mountains, right?
Like, let's go walk around outside, take a hike.
And she's like, no, I don't want to do that.
I want a manny.
I want a petty.
I want a massage.
And you have to pay for all that.
Oh, boy.
went out to like a really nice dinner that I paid for.
She kept asking without the dinner.
How was it that I didn't know there was some snow?
We understand, Calvin.
Shame on the woman for not being happy when you didn't deliver on the promises that she put up there.
We're on your side with that.
The weird part that we heard from Kelly, and you can say whether this is true or not, is when she left, she forgot her bag over at your place.
And she's asked for it back and you're refusing to send it to her.
Yes, that is totally true
That seems whether or not you had a bad time
on the date, that feels like you're
crossing the line and like not returning
her items. I don't know.
Hear me out here. I don't think you know
the whole story about this. So she left me a message
and her message was, hey, I'm with a different guy in New York
and you just send my bags to his place.
One week later, right?
That's like her revenge tactic.
Like, I'm going to show him. I'm with somebody else already.
Oh, boy.
She's already got this other guy and she wants me to send the bag.
there and she sends me the address.
I look up the address.
It's like a multi-million dollar
condo in New York.
You know what?
No, I'm not sending your bags
of some other rich dude
who you already, you know,
had lined up there a week later.
You know, I'm not paying,
I'm not paying another cent for this woman.
Yeah, but you should have told her to come pick it up
at the front desk of Europe condo building.
Yeah.
She can.
I will say, Calvin, we did not hear that part of the story
about the other guy in New York
and she wants you to mail it directly to him.
I got to say rich people problems are so juicy.
Yeah.
Very fun.
And it gets even juicier for you, Calvin, because Kelly is on the other line right now,
waiting to jump in and talk to you.
Oh, really?
Yeah.
Go for it.
Put her on.
Yeah.
Okay.
Kelly, jump in.
This is the battle I want.
Hi, Calvin.
Oh.
Oh, hi, Kelly.
I don't receive that package yet.
Perhaps it was delayed in the mail.
What?
Oh, no.
You just listened.
Yeah, it was delayed in the mail because it was been paid for because I'm not paying for anything
else.
But honestly, like, I would do you.
the favor of bringing it downstairs and leaving it with my
doorman so the FedEx guy doesn't
have to ring my bell. Wow.
This is punitive and it's childish, Calvin.
Just call your assistant. This is a two-second problem.
Oh, wow. He's childish.
It's not about the time, Kelly. It's about the money.
I spend thousands of dollars on you.
What would it cost $120 to set the package?
I'm about you have your rich New York boyfriend
pay for it if you can because it seems like you can't pay
for anything. Oh, Josh Myers!
Okay, now you're childish and jealous, Calvin.
Oh, jealous.
Really grow up.
I will say, Kelly, it's a little odd that you didn't mention this second part of the story where you've moved on to a new guy already.
I don't even think any of that matters.
It's all could have been avoided if you weren't so entitled and you just told them like, hey, I'm not having a great weekend.
Well, be careful with the E word on this show, bro.
I want to leave, and Calvin, I'm sure, would have taken you back to his place to get your bag and then taking you to the airport.
Yeah.
I absolutely would have done that.
Yeah.
Oh, so you wanted me to believe that he was going to.
drive me back to his place, get my luggage, and take me to the airport, just like you wanted
me to believe there was snow on the mountain.
Oh.
He didn't lie about the snow.
He didn't.
That was a good one, though.
You got to give it.
There's no lie.
She has a point you don't follow through with your promises.
Yeah.
I can't promise snow.
I mean, you know how ridiculous this woman is?
Yes.
Please.
If there was no snow on that mountain, you should have flown us to another resort where there was snow.
Oh, that is a good point, Calvin.
You say that you're able to adapt on the fly.
Yeah, you did another country's mountains.
Yeah, you didn't come through this time.
I mean, obviously not meeting up to Kelly Standards.
It's fine by me, but she found another man who does.
So why doesn't she fly immediately out to my place and pick up the bag?
I know you're trying to stand your ground on this one,
but I feel like the headache is just going to be over if you ship her the damn bag.
Like it's like...
Calvin, listen to them.
Please don't drag this out.
It's ridiculous.
You know that my new boyfriend is a lawyer.
Oh.
Oh.
Are you threatening me now?
I mean, just saying don't make this more complicated than it is.
Oh, my gosh.
We are living for this drama, but we are running out of time here.
So normally at this point, I would ask, would you go out on a second date and we would pay for that.
But this time, I'm going to ask Calvin, would you be willing to ship Kelly her bag?
at her new guy's place.
And we will pay, since I don't know how much it will cost,
let's say half of the shipping price.
Assuming it's not overnight delivery.
No, no, no.
We're doing seven to ten business days.
Okay, she doesn't deserve.
Ground shipping, and we'll help chip in for that.
Guys, I don't need or want you to have to pay for this.
And honestly, like, I had a good time with this argument,
but now I'm just, I'm fucking annoyed, okay?
Bye, Kelly.
Maybe the bag will show up.
Maybe it won't.
It'll be in our street corner.
Hey.
Someone's going to find it and be excited.
You should start opening bags on the street corners.
Brooke and Jeffrey in the morning.
In the middle of the night,
Saskia awoke in a haze.
Her husband, Mike, was on his laptop.
What was on his screen would change Saskia's life forever.
I said, I need you to tell me exactly what you're doing.
And immediately,
the mask came off.
You're supposed to be safe.
That's your home.
That's your husband.
So keep this secret for so many years.
He's like a seasoned pro.
This is a story about the end of a marriage.
But it's also the story of one woman
who was done living in the dark.
You're a dangerous person who prays unvulnerable
and trusting people.
You're creditor, Michael Levin' Good.
Listen to Betrayal Season 5 on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
New Year, new goals, and in this economy, a better money plan is more necessary than ever.
I am Matt.
And I'm Joel.
We are from the How to Money podcast.
And every week, we help you to spend smarter, save more, and make sense of what's going on out there.
If you want 2026 to be the year you finally feel in control of your money, we're here.
here to give you the tools and advice to help you make it happen.
Listen to How to Money on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
There's something so poetic about a broke radio station offering to help rich people pay to
ship their stuff across the country for them.
That woman was not rich.
I think she was poor.
I think she lied on that dating app to get on there.
She wouldn't come to us for free advice if she actually had money.
Okay, but all of her boyfriends are rich, so that makes her rich by associate.
I know, but like, a rich guy isn't even going to want to fight for any woman after they've only known him a week.
Yeah, they can just move on to another one.
She just met this guy in New York.
She's like, you're going to have to be the lawyer for my kid.
He doesn't care.
I do think it's funny, though, that normally we offer an entire meal, a whole day of gift cards at the end.
But we can only afford to fly half of a purse around the country.
We couldn't even do the whole thing.
Oh, is her purse?
I thought it was her bag, like that she stayed with.
She said a small bag, so I'm assuming it's like a large purse size.
Yeah, it's probably like a Russian, a Russian doll sort of situation with a really nice big bag with a really nice smaller bag inside and an even smaller tiny bag.
Can we, do we have Calvin's number saved?
Hey!
Oh, you'd like to get in touch with them.
He sounded pretty cool.
Yeah.
I mean, I don't know what's going to happen with those two.
Will he ship the bag?
Will her new rich New York boyfriend buy her a new set of Louis Vuitton?
luggage. Will the stitching inside even be in the color that she likes?
Probably not. So many questions will probably never know the answers to.
That's white, not cream. Oh, man. But one question that we can't answer, possibly,
is why isn't that guy or girl not calling you back? Reach out to the show and we can help
get it answered for you. Find us online at Brooke and Jeffrey.
In the middle of the night, Saskia awoke in a haze. Her husband, Mike, was on his laptop,
What was on his screen would change Saskia's life forever.
I said, I need you to tell me exactly what you're doing.
And immediately, the mask came off.
You're supposed to be safe.
That's your home.
That's your husband.
Listen to Betrayal Season 5 on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.
Hey, it's Joel and Matt from How To Money.
If your New Year's resolution is to finally,
Get your finances in shape.
We've got your back.
Prices, they're still high, and the economy is all over the place.
But 2026 is the year for you to get intentional and make real progress.
That's right.
Yeah, each week we break down what's happening with your money,
the most important issues to focus on, and the small moves that make a big difference.
Kick off the year with confidence.
Listen to how to money on the IHeart Radio app, Apple Podcasts,
or wherever you get your podcasts.
What if mind control is real?
If you could control the behavior of anybody around you,
What kind of life would you have?
Can you hypnotically persuade someone to buy a car?
When you look at your car, you're going to become overwhelmed with such good feelings.
Can you hypnotize someone into sleeping with you?
I gave her some suggestions to be sexually aroused.
Can you get someone to join your cult?
NLP was used on me to access my subconscious.
Mind Games, a new podcast exploring NLP, aka neurolinguistic programming.
Is it a self-help miracle, a shady hypnosis scam, or both?
Listen to Mind Games on the Iheart Radio app, Apple Podcasts, or wherever you get your podcasts.
This is Dr. Jesse Mills, host of the Mailroom podcast.
Each January, men promise to get stronger, work harder, and fix what's broken.
But what if the real work isn't physical at all?
I sat down with psychologist Dr. Steve Poulter to unpack shame, anxiety, and the emotional pain men were never taught how to name.
Part of the way through the Valley of Despair is realizing this has happened,
and you have to make a choice whether you're going to stay in it or move forward.
Our two-part conversation is available now.
Listen to the mailroom on the IHeart Radio app, Apple Podcasts, for wherever you get your favorite shows.
A new year doesn't ask us to become someone new.
It invites us back home to ourselves.
I'm Mike Delarocha, a host of sacred lessons, a space for men to pause, reflect, and heal.
This year, we're talking honestly about mental health, relationships, and the patterns we're ready to release.
If you're looking for clarity, connection, and healthier ways to show up in your life,
Sacred Lessons is here for you.
Listen to Sacred Lessons with Mike Dellerooch on the IHartRadio app,
Apple Podcasts, or wherever you get your podcasts.
