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October 17, 2025 17 mins

In today’s Second Date Update we had a listener caught in the most awkward position you could hope to be in on a first date. Find out what it was in the podcast!

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Speaker 1 (00:00):
Second date, up date when your date plans change at
the very last second, not by your choice, but because
of like an unforeseen obstacle with the venue, like the
baseball game got rained out, the KFC ran out of Chicken.
That doesn't happen. What's your mood?

Speaker 2 (00:21):
Like?

Speaker 1 (00:21):
How do you respond? You could instantly give up right
there and say no, I'm not doing this. I'll FaceTime
you from my bubble bath, but I don't pivot on
the flo.

Speaker 2 (00:30):
Yeah, be flexible, Jeb, spontaneous.

Speaker 1 (00:33):
That is the other option. Shake it up, do something new.
And apparently that's what one of our listeners, Sierra, had
to do recently on her date, and I'm curious what
that looked like. So Sierra, welcome to the show.

Speaker 3 (00:46):
Hi.

Speaker 2 (00:48):
You sound like go with a flow type of person.

Speaker 1 (00:51):
Sound like a lady. That's good. Sorry to hear that
your date plans crash, but tell us what happened.

Speaker 4 (01:00):
So I met this guy, Ashwyn on a dating app.

Speaker 2 (01:04):
Oh, he sounds fancy and rich. His name is Ashwyn.

Speaker 1 (01:08):
I don't know how to spell that.

Speaker 4 (01:09):
Yes, not gonna lie. The name intrigued me. But what
I really liked the most was he was funny, which
is so important. But he was also playful, Like he
was kind of saucy, but not disrespectful, you know what
I mean.

Speaker 1 (01:24):
A little bit but like totally joking. Yes, like talking
to your grandpa, but sixty years ago that everybody has
a grumpy grandpa who likes to poke fun at them,
right grumpy?

Speaker 2 (01:36):
Yes, Oh, it's like he's not an old man.

Speaker 1 (01:38):
He's flirty. His name is Ashwyn.

Speaker 2 (01:41):
He sounds like, Okay, you got us there, Jeff, but
the rest lost us.

Speaker 1 (01:47):
Okay, well we all have different images of what Ashwyn is.
But what was the plan for the date?

Speaker 4 (01:53):
Well, you know, I'm happy to say that wasn't my
first impression. I liked him. I liked him enough to
uh say yes to a date with him, and I
think that he was kind of trying to impress me,
which obviously is fine with me. Like he had made
rooftop bar reservations at this like trendy place always good.

Speaker 1 (02:14):
Yeah, a rooftop bar. That's like not cool.

Speaker 2 (02:18):
I don't know why, you know, like you put him
in a basement, not awesome, but on the roof it
means something.

Speaker 1 (02:25):
Yeah, Okay, so you sound like you're excited to get
some rooftop drinks.

Speaker 2 (02:30):
Oh.

Speaker 4 (02:30):
I was so excited. I love this kind of thing.
And he seemed exactly like his profile. He was super cute,
super nice, funny everything that I was hoping. We go
up the elevator and the guy at the door said
he was so sorry, but the whole place was closed
for like some kind of a cryptocurrency event.

Speaker 1 (02:51):
God crypto thing, Yeah, I know people who could afford
to rent out it into money.

Speaker 2 (03:01):
I just picture a bunch of dudes with receding hairlines.

Speaker 1 (03:05):
Yeah, telling each other the same thing popper vests. Yeah, careful,
you're turning a Lexus on to Oh no, but that's
what a bummer. Your whole playing for the night just
got totally ruined.

Speaker 4 (03:18):
Yeah, I mean it was really disappointing, and I could
see the Ashman looked so disappointed, like, you know.

Speaker 1 (03:24):
That shows you he was excited for the day too.
So what did you do?

Speaker 4 (03:28):
So I just said, screw it, let's take a walk.
I'm not wearing the greatest shoes for it, but I
just really wanted to spend time with him at that point.
So we walked down the street and we walked and
talked for a while, and we just kind of ended
up at this old like it was just like a diner,
like a normal you know. Okay, Okay, it wasn't like
a cute like, oh we're trying to be retro diner.

(03:48):
It looked like it had just been there for like
seventy years.

Speaker 2 (03:53):
Yeah, the grease trap hasn't been pawned in at least
two years.

Speaker 4 (03:57):
But that's what makes the price taste so good.

Speaker 1 (04:00):
Okay, we're putting a lot of emphasis on like the
location of the day, But what about the bond, the
connection between you and Ashwynd. Did that change once you
ended up at the crappy diner?

Speaker 3 (04:11):
No?

Speaker 4 (04:11):
I mean it was honestly, it was kind of perfect.
Like we were sitting there eating cheese fries and drinking
milkshakes in our formal clothes and just talking, you know,
And probably because the plans had changed and we were
thrown in the situation, we ended up having just the greatest,
most real conversation.

Speaker 2 (04:30):
It was that awesome. That's such a good sign for anyone.
If you can be anywhere with someone and still have
a good time, that means that you actually have a
real connection.

Speaker 4 (04:38):
Yes, and after our plans fell through, you know, like
it just felt so good. It felt so comfortable talking
to him. We've talked for hours.

Speaker 5 (04:46):
Oh my gosh, how could he not become Yeah, I mean,
how did this night end?

Speaker 4 (04:51):
Well? Okay, so one thing led to another. He kissed
me good night, and he did, of course, end up
at his plant.

Speaker 1 (05:01):
Really post chili cheese fries. You guys went.

Speaker 3 (05:06):
Hey.

Speaker 4 (05:06):
I'm telling you, I felt very comfortable with him, and
apparently I didn't leave till the next morning, impact, which
is unusual for me.

Speaker 2 (05:15):
But what did he say? Was he there when you
woke up?

Speaker 4 (05:18):
Yeah? No, he was just his sweet, playful selfie give
me a little kiss on the nose, which I thought
was adorable and.

Speaker 2 (05:23):
Okay, so it wasn't even awkward the next morning, Yeah.

Speaker 4 (05:27):
Not at all.

Speaker 1 (05:28):
It makes me wonder if it was like one of
those typical guy things where it wasn't enough of a
challenge and it became too easy, so the guy gets bored.

Speaker 2 (05:36):
He doesn't sound like a guy that is like that, though, Jeff,
this sounds like they never charger until It sounds like
they were just vibing on a deeper level than that.
If he just wanted to get in her pants and
that's all he wanted, or he was disappointed in that
they could have gone anywhere and just gone and drank
and then gone back to her place.

Speaker 1 (05:57):
It sounds exactly like what they did.

Speaker 2 (05:58):
Oh, they would do a die. They talked for hours,
they walked the city like that is a totally different thing.

Speaker 1 (06:04):
Maybe he knew that crypto event was happening and this
was all set up as like a little ruse to
be like, look at me, Look how spontaneous I could be.
Let's go back to my class.

Speaker 2 (06:13):
You are so cynical against men right now.

Speaker 1 (06:15):
Yeah, I'm just telling you this. I've heard guys do
stuff like this and sometimes even worse.

Speaker 2 (06:20):
I know, I still want to thank for the best, Jeff,
I'm sorry.

Speaker 1 (06:23):
All right, Well, you can be naive if you want,
but let's call Ashwin and we'll see what he has
to say. With your second date update right after this
hold on second date update. Wow, another first date blown
up by a pod of crypto bros. Every single week

(06:44):
we deal with this because our listener Sierra was supposed
to meet a guy named Ashwin at a rooftop bar,
but of course, when they arrived, the entire venue had
been rented out by a bunch of crypto nerds he
can out over yield farms and stabilizing their coin pools
whatever they like to talk about. Look at these candlesticks popping.

(07:05):
I've done a little training. You don't even know what
that means, but it disgusts me.

Speaker 2 (07:09):
No wonder, I don't enjoy any of it.

Speaker 1 (07:11):
Here's the thing. Sierra and Ashwin didn't let that kill
their night. They actually swung it into a really fun
evening at a local diner, which eventually led into a sleepover.

Speaker 2 (07:23):
Sounds so sweet, it did.

Speaker 1 (07:25):
Until Ashwyn is suddenly not calling her back.

Speaker 2 (07:28):
Dude, he kissed her on the nose for goodness sake, Like, yeah,
like that's a I really like you move.

Speaker 4 (07:37):
Is there another way to read that?

Speaker 2 (07:39):
See? Yeah, it's so sweet. And you've reached out to him,
or you haven't. You're just waiting to hear from him.

Speaker 4 (07:46):
This was what was so weird. We texted a little
bit after that, but he just I got the vibes
that he was not interested.

Speaker 1 (07:54):
Even through texts. Yeah, yeah, I feel ery shift for sure.

Speaker 2 (07:59):
I hope it's one of those where he's just scared
of real love.

Speaker 1 (08:04):
It's not stupid, but sometimes, like you had said, I
do no challenge.

Speaker 3 (08:07):
Like if it's too easy and everything is great, sometimes
people don't like to.

Speaker 1 (08:11):
Be in that space. I don't know. We'll see which
category Ashwin falls into if we're able to get him
on the phone. Dial his number right now, perfect category.

Speaker 4 (08:20):
Yeah.

Speaker 1 (08:20):
Yeah, we're praying for a Disney ending, getting.

Speaker 2 (08:24):
Her another nose kiss, jeff.

Speaker 1 (08:27):
What a promise. So here we go. Hello, Hey is
this Ashwin?

Speaker 3 (08:43):
Yeah?

Speaker 1 (08:44):
Hey, man, thanks for answering. You're on a radio show
right now. It's called Brook and Jeffrey in the Morning.

Speaker 2 (08:49):
Hey, good morning, Welcome to the show. Ashwin. Hi, it
sounds like you might be busy or something right now.

Speaker 1 (09:00):
I hope you have a second to talk to us,
because we're doing a segment called a second Date update.

Speaker 3 (09:06):
Sure this is weird, Okay, yeah.

Speaker 1 (09:11):
You give him a lot of credit. So the reason
that we're calling is because you went out on a
date recently with a listener to our show, a woman
named Sierra.

Speaker 3 (09:23):
Oh yeah, you mean.

Speaker 1 (09:26):
He lost a nice So here's the thing, Sierra. We
talked to her and she told us about your hang
the other night.

Speaker 2 (09:34):
The diner sounded so cute.

Speaker 1 (09:36):
It sounded pretty good. Despite all the obstacles that came up.
You two were able to have a really good thing.
Would you agree with that?

Speaker 3 (09:43):
I mean, we we did. It was probably one of
the most amazing dates I've ever been on.

Speaker 1 (09:49):
What heck bro where we're here waiting to find like
crazy reason? Yeah, that's so sweet. Sorry to be so
emotional about it, but it's just that, you know, Sierra
is really confused.

Speaker 3 (10:02):
It's just kind of embarrassing for you or for Sierra.
For me.

Speaker 2 (10:08):
Well, I mean, if it's too much to share.

Speaker 1 (10:11):
You should do it anyway, because I don't want to
pressure anybody, you know, and Sierra really deserves to know,
wouldn't she say?

Speaker 3 (10:21):
Yeah? Yeah, no she is. She's really awesome. This is
mostly mostly a me a meet thing.

Speaker 1 (10:28):
Okay, Well, if you're willing to open up to us,
just even a little bit, and we could pass the
message to her, I think that would go a long way.

Speaker 3 (10:36):
We have this amazing, amazing night. And she told me
that she doesn't do this a lot, where she goes
to a guy's place, and that she was curious where she.

Speaker 1 (10:47):
Ranks, oh, where she was where she ranks like compared
to other people.

Speaker 3 (10:55):
Yeah, I was very I was very thrown off by
that question.

Speaker 1 (11:00):
Weird question.

Speaker 2 (11:01):
A joke, Yeah, it was.

Speaker 3 (11:05):
It was not a joke because I asked her to clarify.
I said, what do you mean? And she said, well,
I'm sure you've been with X amount of people.

Speaker 2 (11:14):
Kind of a rude assumption, an assumption person, but you
know what, or it's a testament to your experience that yeah,
you could take it as a compliment.

Speaker 1 (11:24):
What did you mean? Did you actually rank her?

Speaker 5 (11:27):
God?

Speaker 3 (11:27):
No, Well, I told her that I'm not sure how
to answer that. It's good, and eventually I said top
three for sure.

Speaker 2 (11:36):
Oh that's cute. That's answer.

Speaker 1 (11:38):
I was like, what am I take? Top three? That's great?
And you don't want to say number one because then
you're too eager and I don't believe.

Speaker 2 (11:46):
It if you say number one.

Speaker 3 (11:51):
But then I told her, since I answered this for you,
you have to reciprocate.

Speaker 1 (11:56):
Why would you do that?

Speaker 3 (11:57):
You about that?

Speaker 1 (11:58):
She asked it to him? Oh god, what did she say?

Speaker 3 (12:02):
She said, you're definitely in my top five.

Speaker 1 (12:05):
Okay, not that she a little bit lower than what you.

Speaker 3 (12:11):
Yeah, it gets worse. I asked her out of how many? No,
and she said maybe five.

Speaker 1 (12:20):
Oh wow, so you're in the top one hundred percent.

Speaker 2 (12:25):
That changed everything for you soon, because it just changed
everything for me.

Speaker 1 (12:30):
What did you assume?

Speaker 3 (12:31):
It just kind of felt it felt a little humiliating.

Speaker 2 (12:36):
Did you tell did you laugh? Or did you say? Okay,
that's rude.

Speaker 3 (12:39):
I didn't really know what to say because I already
felt so vulnerable. You know, we're in my bed, naked
and we've been together.

Speaker 2 (12:46):
Okay, it's like getting a participation trophy.

Speaker 1 (12:53):
Yeah. Well, you know, maybe maybe there was some sort
of miscommunication or she didn't say quite what she meant.
And I'll give her a chance to explain herself right here,
because I need to let you know. Sierra is on
the other line of this call listening, wanting to talk
to you.

Speaker 2 (13:07):
Oh god, she's the one that should be embarrassed.

Speaker 1 (13:13):
Hi, please tell us. Five is like the number one ring,
like it's the best.

Speaker 2 (13:19):
Oh yeah, you were going backwards.

Speaker 1 (13:21):
Yeah yeah, She's like, I can't trying to say you.

Speaker 4 (13:27):
I feel so bad. First of all, Ashwin, I'm so
so sorry. I can't believe I made you feel that way,
and you've been feeling that way this whole time.

Speaker 1 (13:40):
Does that feel good as knowledge she did something wrong? Yeah?

Speaker 3 (13:45):
Yeah, thank you, thank you?

Speaker 4 (13:50):
I mean you're still top five, Okay, if I if
I explain.

Speaker 1 (13:56):
A little bit, yes, go into details about what.

Speaker 2 (14:01):
Hey, you know what men that can take constructive.

Speaker 1 (14:06):
Through four half one thing he could do better. Let's
work on one step at a time.

Speaker 3 (14:11):
And for some reason I didn't do enough fourth place stuff.
I am I'm open to.

Speaker 1 (14:20):
Do.

Speaker 2 (14:21):
Not interrupt that statement, Jeffrey, not enough men make it.
You should assume you didn't.

Speaker 1 (14:26):
Okay, well, you know, actually, maybe we shouldn't be asking
what he could change. Maybe it's better to ask you, Sierra,
why you said that to him?

Speaker 4 (14:35):
Yes, when I said, oh, you're definitely in the top
five of five, I was trying to be playful. I
was trying to make a joke. I was trying to
be kind of saer ding. Yes, I was kidding enough.

Speaker 1 (14:52):
Yeah, it was a joke.

Speaker 2 (14:55):
Good after sound button or something we could have hit there.

Speaker 4 (14:59):
He definitely top four for sure.

Speaker 2 (15:06):
I think it doesn't matter.

Speaker 1 (15:07):
It's better. Ye, you have to do anything that was great?

Speaker 3 (15:13):
Can we can we please stop talking about one number
i'm ranking.

Speaker 4 (15:19):
Yes, I'm so sorry. I'm just so embarrassed. I was
trying to make a joke.

Speaker 5 (15:24):
You definitely have said your apology I think gets the
idea that you didn't mean it, but we mean this
when we say we'd like to send you out on
another date, the two of you, Ashwyn, if you're willing
to give her one more chance, we would don't let your.

Speaker 2 (15:38):
Pride stand in the way of this one Ashwin.

Speaker 3 (15:41):
Yeah. No, her explanation definitely definitely makes me feel better
and embarrassed that I can't take jokes about bedtime. But yeah, no,
I definitely would be interested in another date.

Speaker 1 (15:58):
All right, so congratulate relations. That means Sierra, you got
what you came for another date.

Speaker 4 (16:03):
With Thank you so so, so so much.

Speaker 2 (16:07):
Oh my god, I feel like we just had two
listeners who own their own mistakes, which was just wild
on this show. Yeah, it never happens to be really
bad at.

Speaker 1 (16:20):
Jeffrey in the Morning. Can we all agree? Where do
I rank? Is a question that should not come up
until at least date number three.

Speaker 2 (16:31):
Let them tell you you just don't ever you never.

Speaker 1 (16:33):
You've never had that conversation with your husband.

Speaker 2 (16:35):
God no, why would you have that conversation?

Speaker 3 (16:39):
You just let someone tell you that was the best,
that was great, or you just.

Speaker 1 (16:43):
Don't bring it up.

Speaker 2 (16:45):
Conversations have it's a funny joke was actually really good.

Speaker 1 (16:51):
I don't know if she really was joking, but it
was the right thing to say in that moment.

Speaker 2 (16:57):
Well, finally, finally, the right thing to say exactly.

Speaker 1 (17:00):
And I fully expect to hear from both of them
when we do an update day. I think, yeah, we're
hopefully by then he's climbed the rankings into her top three.
But what she hasn't added like ten.

Speaker 2 (17:13):
More n we know what type of relationship they're going
to be, right, That's also true.

Speaker 1 (17:21):
I can't say we are open to our listeners ranking
us on our podcast. I hope we're in the top five,
top ten, we'll take top thirty. Even as long as
we're ahead of JLD, than we are a big win
in our books. You just lie and say we don't
even have a list Yeah, we're this before go and
find us wherever you get your podcast. We're up Abro

(17:43):
and Jeffrey
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Brooke Fox

Brooke Fox

Jeffrey "Young Jeffrey" Dubow

Jeffrey "Young Jeffrey" Dubow

Alexis Fuller

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Jose Bolanos

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