All Episodes

June 14, 2025 36 mins

Part 1

Brooke has seen a lot in her 400 years in radio, but today one of our listeners put her in the most DRAMATIC and UNCOMFORTABLE situation of her entire career.

Part 2

There’s some topics you just don’t bring up on a first date. One of our listeners didn’t follow that rule and now it’s no surprise he needs our help in a Second Date Update!

See omnystudio.com/listener for privacy information.

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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Hey, it's Brook and Jeffrey in the morning. This is

(00:01):
the Second Date podcast. Thank you so much for finding us.

Speaker 2 (00:04):
On a weekend. Yeah, on a weekend, and this.

Speaker 3 (00:06):
Is just a little treat. Okay.

Speaker 1 (00:08):
When it says classic, these are ones that we have
dug up from the vault because we have done thousands
of second games, so.

Speaker 4 (00:16):
You maybe probably have not even heard these ones.

Speaker 5 (00:18):
Black people are always think they're new, and we're like,
that's a classic.

Speaker 6 (00:21):
Yeah.

Speaker 2 (00:21):
A lot of you guys have bing these, but not
everyone is as.

Speaker 1 (00:25):
Committed as you yet totally, it's definitely split fifty to fifty.
I mean, no matter what, we just hope that you
enjoy this. We've got two back to back to just
make sure that you get all your tasks, all your
chores done with one pod.

Speaker 2 (00:37):
Okay, yeah, so.

Speaker 5 (00:38):
You can't get your stuff done without us. Yes, you
know it. That's right.

Speaker 3 (00:41):
So it all starts right now.

Speaker 5 (00:44):
I will say there's not much that really rattles Brook
anymore because four hundred years of radio experience, she's seen
and done pretty much everything.

Speaker 4 (00:56):
Oh say it again, Jah, she was ir when Station
one start.

Speaker 5 (01:00):
Well that's what she thought till today when she was
put in the most dramatic, uncomfortable situation of her entire
radio career.

Speaker 3 (01:10):
You are even exaggerating.

Speaker 5 (01:11):
All because our listener said, Brook, please, you need to
talk to this person for me.

Speaker 3 (01:18):
But I don't have boundaries, so I didn't say no.

Speaker 5 (01:21):
And I probably should have. Did Brook handle it with
poison class or did she crumble under the immense pressure.
You're gonna find out when we do your second date
update right after this second date update. We've heard of
people getting stood up at the start of the date. Yeah,
just never showing.

Speaker 3 (01:41):
It's not cool, feels so bad.

Speaker 5 (01:44):
I've been stood up at the end of a date
where night's over, we say goodbye, and then they just
leave that. Oh you're standing at the door, so rude.

Speaker 3 (01:52):
That's the events.

Speaker 5 (01:54):
At least linger for a second before you run away.
But it's a whole different thing to get stood up
while you're still in the middle of a date.

Speaker 3 (02:04):
I know a lot of people go into the bathroom
and then yeah, but.

Speaker 5 (02:08):
This is different. This isn't like an excuse yourself to
the bathroom mid dinner, then slip out the back situation.
This one's more personal. Apparently that's what happened to one
of our listeners Dana recently, so let's talk to her. Dana,
I'm sorry to hear this happen to you. How you
doing I'm.

Speaker 7 (02:24):
Not doing well. I'm a little piss off right now.

Speaker 5 (02:27):
To be honest, it's understandable.

Speaker 1 (02:30):
I mean, I don't even really get how whatever you're
describing happened.

Speaker 2 (02:33):
I'm thinking one of those on me at the second bar.
Let's drive separate see it ever, to learn more.

Speaker 5 (02:37):
About what happened on this date, Dana tell us the situation.

Speaker 7 (02:41):
So I got stood up on a vacation dates.

Speaker 3 (02:44):
A vacation date, like when you met somebody at a resort, you.

Speaker 7 (02:47):
Mean, not particularly. I had met this guy, Sean on
one of the apps. I don't know if it was
travel mode or you know, his search options were everywhere,
but we connected. Okay, he's super cute, he's athletic, all of.

Speaker 4 (03:03):
Us on the app.

Speaker 7 (03:04):
Just so you know, well, I had a high hope. Okay,
good and honestly, like we really got along. We were
talking a lot, We're even talking on the phone. And
after a couple of weeks he he wanted to fly
me to LA which is where he.

Speaker 1 (03:23):
Okay, now, is that like a green flag for you
or are you worried about that?

Speaker 7 (03:28):
Have you?

Speaker 3 (03:28):
Have you done it before?

Speaker 7 (03:30):
I haven't. At first, I was a little scared, but
it was also kind of thrilling to me to be
a close like kind of felt romantic.

Speaker 2 (03:39):
I've heard both like amazing stories and horror and.

Speaker 5 (03:43):
It's a red flag that his entire family is waiting
at the air I'm just assuming that's how it went.
I don't know, though, Yeah, did you go?

Speaker 3 (03:51):
Did you get on the plane?

Speaker 7 (03:53):
Yeah? I took the invitation, but obviously I was feeling nervous, like,
how was I going to go about this? You know,
I it I didn't know him. I wasn't going to
stay at his house as.

Speaker 4 (04:04):
To get you a hotel or did you offer for
you to stay in his place? There's two big differences here.

Speaker 8 (04:08):
Yeah.

Speaker 7 (04:08):
No, I mean I set the boundary pretty quickly, and
he offered to get me a hotel room.

Speaker 3 (04:15):
I can't wait to hear them. You see him?

Speaker 7 (04:17):
So it all turned out really well?

Speaker 1 (04:22):
Yeah?

Speaker 7 (04:22):
No, I mean like when I finally met him, he
looked like his photos. We hung out all day long.
He showed me around the city.

Speaker 3 (04:28):
That's so cute.

Speaker 7 (04:30):
Yeah, we had a nice dinner. We went dancing. I
felt like it was a really good date. We got
along really well. He was really easy to talk to.

Speaker 5 (04:36):
Like, Okay, well, I don't understand then, because at the
start you said you're really pissed, So how does that
emotion come into play?

Speaker 7 (04:44):
Well, because the next day, after this great date, we
had plans to go to this really nice lunch place.
It's really hard to get into, and I was really
excited about it. And that morning I was hanging out,
I went on to the pool and I texted him.
You know, I was just trying to be like, let's
feed up early. That's hard to get into. You know,

(05:05):
I don't live here, so I don't know how long
it's going to take to get anywhere. And he didn't
respond at all.

Speaker 9 (05:12):
No no response, Oh man, are you like I would
be kind of like, oh, something must have happened, you
know what I mean, Like, you wouldn't assume that somebody
would fly you all the way out there and then just.

Speaker 5 (05:24):
Not did she right? Yeah? Did you ask?

Speaker 6 (05:27):
Yeah?

Speaker 7 (05:28):
So I texted him again, there's still no response. I
ended up getting an uber and going to the restaurant.
He didn't show.

Speaker 3 (05:36):
Up, Oh my gosh, And.

Speaker 7 (05:37):
I text him again, like where is he and asking
him straight up if he's pitching me, and did he
ever respond? He responded later that evening and he said,
I'm sorry I've been unresponsive. I've had some devastating news.

Speaker 1 (05:51):
Oh god, did he share? I mean god, I mean
that's a pretty good excuse.

Speaker 7 (05:57):
He did not share.

Speaker 5 (05:59):
That's too vague.

Speaker 4 (06:01):
Yeah, like my favorite sports team loses, I'm devastating.

Speaker 3 (06:06):
You assume really bad, like someone in the family died,
or like he got fired or something.

Speaker 5 (06:11):
Okay, so you immediately believe him. As soon as he
says devastating news, he gets a free passage.

Speaker 2 (06:16):
Are you the word devastating?

Speaker 5 (06:17):
Yeah, just like vocabulary.

Speaker 3 (06:24):
You don't give him the benefit of the doubt in
that moment.

Speaker 5 (06:26):
Never never give them the benefit of the doubt. We
will take advantage every time.

Speaker 3 (06:31):
Okay.

Speaker 5 (06:32):
I at least would say, well, I hope no one
passed away or whatever you're going through, I'm so sorry.

Speaker 4 (06:36):
I'm here for you, and then he should say something next.

Speaker 5 (06:39):
Okay, So, yeah, what happened. Where did the conversation go
from there?

Speaker 6 (06:44):
Well?

Speaker 7 (06:44):
I didn't hear from him after that, and I just
decided to fly. I probably out the next day.

Speaker 4 (06:50):
Yeah, I mean, what are you gonna do?

Speaker 7 (06:52):
Yeah, I didn't hear from him, and I'm really wondering, like,
what in the world happened?

Speaker 3 (06:56):
And if you still haven't heard from him.

Speaker 7 (07:00):
No, And it's really confusing. And this is why I'm pissed.
It's because we had such a great date that it
makes no sense that he would just, you know, say
there's devastating news, not share with me what it is.
And then he stood me up. Yeah, how oh, this
has been two and a half weeks.

Speaker 5 (07:18):
Time.

Speaker 1 (07:18):
Can I ask you flew into a new city, he
met you at the hotel.

Speaker 3 (07:22):
Did you ever see his house?

Speaker 7 (07:24):
No? I didn't, but I didn't want to see a house.

Speaker 3 (07:26):
I just wondering if maybe there's like a second family.

Speaker 1 (07:28):
Or a family he's married, or you know, like, yeah,
I just I mean, there's so much you don't know
about this guy.

Speaker 4 (07:38):
I didn't even think about that.

Speaker 7 (07:40):
I did my preliminary Google search of this person. I
didn't find anything about a second family, but you know
that doesn't mean that doesn't exist.

Speaker 5 (07:48):
Did you check the local papers about any devastating news
that could have been.

Speaker 4 (07:53):
Devastation column?

Speaker 3 (07:54):
I love that column.

Speaker 1 (07:56):
I don't even know how you checked the news.

Speaker 5 (08:00):
Why don't you google some devastating information in the Los
Angeles area and when we come back. I don't think
a whole lot of bad stuff happens there. But when
we come back, we'll try and get you your second
date update with with the guy who stood you up
in the middle of your vacation date right after this
hold on second date update when a person you're on

(08:23):
a date with doesn't contact you for a few days
and then finally replies with sorry, I just received some
devastating news but doesn't elaborate. Should that be a red flag?
The ladies in the room surprisingly said no, I think
you need to hear the person believe him. They said,

(08:43):
men don't lie about devastating news.

Speaker 3 (08:46):
Benefit of a doubt, Jeff, that was my exact words.

Speaker 5 (08:49):
Tomato, tomato.

Speaker 6 (08:50):
You know.

Speaker 5 (08:52):
Lexus gives him credit just for using a big word
with lots of letters.

Speaker 2 (08:56):
You can't lie if you're saying devastating.

Speaker 4 (09:02):
So what is it sending him flowers and flying him
to her?

Speaker 6 (09:04):
Now?

Speaker 4 (09:05):
I feel so mad?

Speaker 5 (09:06):
That's so kind. Bottom line is Dana was left hanging
in the middle of a vacation dating. The guy flew
her ound to La and now he hasn't even responded
to her for two weeks after he just ditched her.

Speaker 3 (09:19):
Oh my god, it's wild. I think that he's got
a wife and kids.

Speaker 4 (09:23):
I'm telling you, it's not just devastating. You would have elaborated.

Speaker 1 (09:27):
Days later, he's saying, She's like all the devastating news,
the kids are still.

Speaker 3 (09:31):
In this house.

Speaker 5 (09:33):
That would be tragic. So understandably, Dana wants answers here.
We're gonna call him. His name is Sean, right, Dana, Yeah, okay,
I just want to make sure we have that.

Speaker 3 (09:43):
And how mad are you are you? Because you said
you were. I'm just wondering at what point you're gonna
yell at him?

Speaker 7 (09:50):
I mean, if we can get him on the phone
and I can talk to him like my time is valuable.
I came to a different city to see him, like,
I him a paper of your wife.

Speaker 4 (10:01):
Are gone because of him?

Speaker 3 (10:03):
You got a good story. Yeah, you do it for
the plot.

Speaker 2 (10:07):
Probably nice into stories you were there.

Speaker 5 (10:09):
Yeah, yeah, it's not like we got nothing out of
this trip, but hopefully we can at least get some
resolution for you, assuming he answers the phone. So I'm
gonna dial it right now.

Speaker 7 (10:20):
Good luck.

Speaker 3 (10:21):
All right, they never wished us luck?

Speaker 5 (10:24):
Sweet here we go.

Speaker 10 (10:25):
Hello, Hi?

Speaker 5 (10:38):
Is this sorry? We're looking for Sean? Sean there, No,
he's out for a run.

Speaker 7 (10:44):
Can I take a message for you?

Speaker 10 (10:46):
Uh?

Speaker 5 (10:48):
Yeah? Well well hold on?

Speaker 1 (10:50):
Well okay, I think we just need to ask who's this?

Speaker 5 (10:54):
Yeah, who's this?

Speaker 7 (10:56):
Who is this?

Speaker 6 (10:57):
Or there's several of you.

Speaker 5 (10:59):
Well, we're a radio show. We're called Brook and Jeffrey
in the Morning.

Speaker 3 (11:02):
Is this Shawn's number?

Speaker 5 (11:04):
Yeah?

Speaker 6 (11:05):
Did he sign up for something?

Speaker 4 (11:06):
Are you a family member of Seawan's?

Speaker 6 (11:09):
I mean you could say that.

Speaker 5 (11:13):
What do you mean like you're a sister?

Speaker 7 (11:16):
I'm his wife? Oh?

Speaker 5 (11:18):
Okay, right, so Hi, sorry to bother you. You were
radio show. Do you mind if we put you on
hold for a second?

Speaker 7 (11:28):
I mean, okay, I don't have all the Yeah.

Speaker 5 (11:31):
Sorry, we'll be right back to you. Just hold on.
Can we put her on hold? Yeah? Okay, we got her.

Speaker 3 (11:35):
Oh my god?

Speaker 5 (11:37):
All right, So.

Speaker 2 (11:40):
That to be the truth.

Speaker 1 (11:42):
I was like, worst case scenario.

Speaker 4 (11:45):
I thought you were wrong.

Speaker 3 (11:46):
Oh my god.

Speaker 5 (11:47):
We're kind of called it here. Not it's not an
entire second family, or maybe it is.

Speaker 3 (11:51):
What my wife is a second is the family?

Speaker 5 (11:54):
There might be kids there too, but we have at
least got a wife, Dana. Dana, how are you feeling?
Are you?

Speaker 7 (12:01):
How am I supposed to respond to this?

Speaker 3 (12:03):
Do you want to tell her?

Speaker 5 (12:04):
Or are you still in on Sean? We don't know.

Speaker 1 (12:11):
Well, this is the first time we will not be
offering a second date at the end.

Speaker 4 (12:16):
We can't do this.

Speaker 7 (12:17):
No, this is awful.

Speaker 4 (12:19):
Yeah, I agree.

Speaker 7 (12:20):
First, I have been cheated on before, and the fact
that knowing now that I might be a participant in
somebody else's affair infuriated.

Speaker 3 (12:30):
Do you want to tell her? Do you want to
talk to her? And can we do that? Because I
don't want to tell her.

Speaker 5 (12:34):
Unfortunately, it's not surprising because unfortunately a lot of guys
do end up doing stuff like this. But how do
we want to handle this? Because there's really, in my mind,
there's three options for us to go here. Number one,
we just hang up, We leave it alone, hands off.

Speaker 3 (12:47):
Of it, the coward's way out.

Speaker 5 (12:50):
I'm not opposed to it. Number two wouldn't be Number two,
have Dana speak to the wife and fill her in
on the truth about what's happening.

Speaker 3 (12:59):
She's to do it calmly. If she's gonna do that, it's.

Speaker 5 (13:02):
Not gonna happen, or we go option three, my favorite,
have Brooke speak to the white for Dana. Brook has
been dying to let her rage out onto some sort
of you.

Speaker 2 (13:15):
Do your kids cheating? Don't you want to help?

Speaker 4 (13:17):
And when we started the call, you literally asked, when
you're gonna yell at him? You can do it?

Speaker 8 (13:21):
Now.

Speaker 7 (13:22):
I think that if Brook can set this up, I
think speak to her. But I don't want to. I
just don't want to come in and my god.

Speaker 5 (13:30):
Okay, that's a good choice, Dana. I feel like this
is gonna be really emotional for you. So it's good
to have Brooke, who's notoriously even keel.

Speaker 3 (13:40):
The opposite of even you can the marriage.

Speaker 2 (13:44):
I mean, okay, here's the thing.

Speaker 3 (13:46):
We are not breaking up this marriage. That man is
the one that broke up his mag Absolutely fine, I'll
do it.

Speaker 4 (13:53):
Okay, she's gonna really, You're gonna really do it.

Speaker 3 (13:56):
I mean, somebody has to. This woman has to.

Speaker 7 (13:59):
Know Brook, tell her the truth.

Speaker 4 (14:01):
Come on, I got your back here.

Speaker 5 (14:04):
Excuse devastating news. Let's make it a real.

Speaker 2 (14:07):
Thing word for me forever.

Speaker 5 (14:09):
Now, all right, let's punch the wife back up. Okay, Hello, Hello, Hey,
sorry about that. So we are back and actually my
co host Brooke would like to speak with you.

Speaker 3 (14:24):
I didn't get your name. What's your name, Niki? Hi, Nikki.

Speaker 4 (14:29):
It's a pretty name.

Speaker 3 (14:30):
So you're probably wondering why we're calling.

Speaker 1 (14:33):
How we got your husband's phone number. I'm gonna tell
you not great news on that front. Okay, because the
reason we have your husband Sean's phone number is because
we do a segment on our show called the Second Date.

Speaker 5 (14:52):
Update, typically very fun segment.

Speaker 3 (14:54):
Yeah.

Speaker 1 (14:54):
So typically people go on a first date and when
they aren't getting a call back from that person, and
then we call and find out why, Like what did
they do wrong on the date?

Speaker 5 (15:04):
They were a funny hat?

Speaker 3 (15:09):
Does that make sense, Snicky?

Speaker 6 (15:10):
Sure?

Speaker 5 (15:11):
Yeah?

Speaker 3 (15:11):
Okay, So that's.

Speaker 1 (15:12):
Why we got your husband's phone number. We didn't realize
he was a husband. Your husband apparently flew another woman
into Los Angeles to take her out for a romantic time.

Speaker 7 (15:28):
Yeah okay, I mean we trade off weeks, we do
stuff with other people. I don't really that's any of
your business.

Speaker 3 (15:34):
Oh my god, wait wait wait yeah, that's fine. Are
you in an open relationship?

Speaker 7 (15:40):
Yeah?

Speaker 10 (15:43):
Relieved?

Speaker 5 (15:43):
I am relieve.

Speaker 7 (15:49):
I thought Nikky, I was giving you the whole world
and you were going to add your marriage.

Speaker 1 (15:54):
But it turns out when you're saying you have an
agreement with your husband to like just date other people?

Speaker 5 (16:00):
Yeah, could you pass some of the is that all?
Could you write down some of how that how that
works to open your marriage because Brook might want to know.

Speaker 7 (16:11):
I am not talking you through this.

Speaker 6 (16:13):
Can I go?

Speaker 4 (16:13):
Yeah?

Speaker 5 (16:14):
Okay?

Speaker 8 (16:14):
You know?

Speaker 1 (16:16):
Can you hear my heart beat over the radio?

Speaker 6 (16:20):
Very work out?

Speaker 3 (16:21):
I was so nervous.

Speaker 5 (16:22):
You know, Nikki, thank you so much. We don't want
to steal any more of your time and we really
appreciate you sharing with us. Have a great day, Okay, great,
tell your husband Sean, what's up.

Speaker 4 (16:34):
Yeah.

Speaker 3 (16:35):
This is one of those the more you know, the
more you know, and it's like.

Speaker 4 (16:39):
You don't want to know, but when you know, you're like, oh,
thank goodness.

Speaker 5 (16:42):
Okay, so Nicky's gone. Hey, Dana, good news. Yeah, you
didn't break up a marriage.

Speaker 4 (16:47):
You're one of many women.

Speaker 7 (16:51):
My jaw.

Speaker 4 (16:53):
I forgot. She was so great.

Speaker 1 (16:57):
I'm taking it that Sean didn't let you know that
he was in an open, open relationship.

Speaker 7 (17:02):
Okay, I think really important information you probably could seems
like pre date info.

Speaker 2 (17:09):
I know it was devastating. He had his weekends mixed up. Yes,
it was his turn.

Speaker 5 (17:15):
I'm sure it wasn't part of the rules that he
had to disclose to other people's in a marriage. Anyway,
we are running short on time here, Dana, so I
would love to ask, would you go on another date
with Sean when he comes back from his run with
Brock or something. We'll pay for that.

Speaker 3 (17:32):
How about a girls night me for some cocktails?

Speaker 5 (17:36):
Okay, I was obligated just to offer. That's just what
I have to do.

Speaker 1 (17:39):
Yeah, man, I've never been so relieved at polyamory.

Speaker 8 (17:42):
And freaking Jeffrey in the morning.

Speaker 5 (17:49):
Textboard is blowing up right now at seventy five nine
two with people saying his wife answered exclamation question mark
and she's totally cool with it.

Speaker 10 (17:58):
Yeah.

Speaker 1 (17:58):
I mean, I who did not I have that on
my bingo card nor these.

Speaker 4 (18:03):
I think it was more dramatic for Brook than anyone
on the phone.

Speaker 1 (18:07):
I think the person dating the husband is thinking, Okay.

Speaker 7 (18:12):
Thank you.

Speaker 5 (18:15):
These are the types of wholesome good news stories that
you just don't hear about in the news anymore. That's right,
jeff I hope kt LA runs a story tonight local
married man dates two dozen women, wife is thrilled Disney
movie Oh Man, happy ending today sort of. Hopefully we

(18:37):
can help make your love life less devastating. If you
email the show, we can call that person who's not
calling you back. And by the way, while you're at it,
go check out all of our second dates wherever you
get your podcasts. Yeah at Brook and Jeffrey Brook.

Speaker 8 (18:50):
And Jeffrey in the Morning.

Speaker 5 (18:52):
Certain topics in the dating world are just considered taboo.
Just don't bring them up because you're playing with fire,
like religion, xes you're fetish for hot tubbing clowns. Don't
don't mention it, even though chances are she'd probably be
into it. Save her not to talk about it. I'm

(19:19):
sure it would go great, but just don't do it.
And I've never seen this particular topic mentioned on any
do not mention list, but maybe we should add it
because one of our listeners spent the entire night talking
about it with his date and our reaction was yikes,
no surprise, he needs our help. In your second date update,

(19:40):
right after this second date updated, imagine the one person
you had a huge crush on years ago where you
were always into them, but nothing happened. Fast forward, and
what if that old crush from your past suddenly walked

(20:02):
back into your life.

Speaker 2 (20:03):
Oh my god, it's so exciting.

Speaker 3 (20:04):
You have your chance get you're talking about.

Speaker 1 (20:07):
It's great second chances.

Speaker 3 (20:10):
Okay, you blew your shot the first time, and now
you get a do over.

Speaker 5 (20:13):
Yeah, that's the question. Do you take Jose's approach and say, well,
past is past and just approach it as friends, or
do you take a chance.

Speaker 3 (20:21):
I've never not taken it.

Speaker 2 (20:22):
Tell you your.

Speaker 5 (20:23):
Current spouse and all three of your children, and you
just go for it.

Speaker 3 (20:27):
Please, you're telling me we have a married person.

Speaker 8 (20:29):
On the phone.

Speaker 5 (20:30):
Happiness too, Brooke. Always remember you're talking about me. One
of our listeners had an accidental run with an old
love interest of his and now he's come to us
for some help. His name is Jason. Jason. Welcome to
the show.

Speaker 3 (20:44):
Hey guys, Jason, as my fingers that you're single, buddy.

Speaker 6 (20:48):
I am all right.

Speaker 5 (20:50):
Okay, okay, off to a good start.

Speaker 4 (20:54):
Exadly we would have probably kept going. Yes, conscious feel better.

Speaker 5 (20:58):
Yeah, So apparently you ran into some sort of old
love interest from your past. Tell us about her.

Speaker 6 (21:04):
Well, it's a it's a girl that I used to
work with. Her name's Cassy. And you know, I must
have asked her out half a dozen times, you know,
back when we worked together.

Speaker 5 (21:13):
Oh you did?

Speaker 3 (21:14):
You did shoot your shot a lot for the shot?

Speaker 7 (21:19):
Was?

Speaker 6 (21:19):
She kind of always acted like she thought I was joking,
you know what I mean, like she didn't take it seriously.

Speaker 1 (21:23):
Well that she was probably doing that to save your feelings.

Speaker 6 (21:28):
Maybe it didn't feel good either way.

Speaker 3 (21:32):
Okay, what was her response always?

Speaker 6 (21:34):
Well, she always would just be like, oh, you're so funny,
or you know, we worked together, you know that sort
of thing. And well then she left, right she got
a different job about seven years ago, and I guess
roughly a week ago I ran into her at Target. Okay,
I was like, hey, you know, and you know, we
kind of shared some old inside jokes and caught up.
You know, how you you.

Speaker 3 (21:54):
Didn't just ask her out right there?

Speaker 2 (21:57):
I'm wondering if you're the reason she switched off.

Speaker 6 (22:00):
Yeah, you know, you're getting ahead of me, because I did.
I did ask her out.

Speaker 2 (22:04):
Oh you did.

Speaker 6 (22:05):
I didn't really mean to even ask her out, like
on a date date, because initially she was like hesitant,
and I was like, let's just go get some drinks,
you know, catch up just like friends. And yeah, and
we did.

Speaker 1 (22:16):
And uh, okay, did you say just like friends when
you proposed this? Uh?

Speaker 6 (22:21):
Not really? I was like, it's just drinks, all right, Okay.

Speaker 5 (22:24):
Is there a way to make make drinks just friends?
Like I just want to go out for friend drinks
with you know?

Speaker 1 (22:28):
I just I was wondering if that's what he said
to her when when he asked her out, because then
obviously we know why she isn't friends.

Speaker 6 (22:34):
Yeah, okay, right, right, Well I kind of did it
in the way that I guess just as friends unless
you say yes and minutes more, you know what I
mean that that kind of thing.

Speaker 5 (22:43):
Okay, okay, leave the door open for whatever possibilities happened
that night, that's okay.

Speaker 6 (22:48):
And so she takes me up on it, gives me
your number, I get, we get a The date didn't
really go all that well because I was nervous.

Speaker 3 (22:56):
Oh you're up in your head?

Speaker 6 (22:58):
Yeah? Oh yeah, I was so on my head. So
like the one reference I had of us together and
like knew was that target. So I just kept talking
about stuff that I found at Target.

Speaker 5 (23:08):
Oh god, well, hold on, Like, maybe there's some good
stuff you found.

Speaker 1 (23:13):
If you talked about Yeah, but I'm guessing that he's
not going to Target for the fun stuff men go for,
like vitamins and cream.

Speaker 4 (23:19):
You're so right.

Speaker 5 (23:21):
What did you find there, Jason?

Speaker 7 (23:24):
Oh?

Speaker 6 (23:24):
I mean I found lots of stuff from household items
to cereals that they don't have at my regular grocery store.

Speaker 5 (23:30):
Like, oh, secret cereals is a hot topic.

Speaker 4 (23:33):
I love cereal back off.

Speaker 1 (23:35):
That sucks too, because you've spent seven years going over
in your head what you would have done differently, and
then your moment comes and all you can talk about
is cereals at targets.

Speaker 4 (23:45):
It does sound that.

Speaker 5 (23:46):
Target would be happy with that, though, like they would
consider that a major romantic win.

Speaker 6 (23:50):
You might be overselling it a little bit. I wouldn't
say that I've spent like the last seven years, like
constantly thinking about that. Okay, just like what I saw
or was like this is perfect.

Speaker 5 (23:59):
Yeah, yeah, okay, Okay, that's good. I don't I don't
think that sounds like a total disaster of a day.
It's just one funny moment.

Speaker 6 (24:07):
Look, she was laughing. She acted like she was interested
in what I was saying.

Speaker 2 (24:11):
So she acted That's the keyword there, like.

Speaker 1 (24:15):
Yeah, just like she laughed at every other joke that
he made when he asked her out, Jason, is.

Speaker 5 (24:20):
It possible that she was just like pretending to be
interested and have more fun than she really was.

Speaker 6 (24:27):
I don't know. I will say that I was definitely
a lot more confident in how well it went before
this conversation.

Speaker 5 (24:34):
We do have that effect on people, So don't look
at yourself for that.

Speaker 7 (24:37):
You know.

Speaker 6 (24:37):
She gave me the normal laughs and asking questions, even
about different stuff, and so I thought she was interested.
And I shot her at the text message the next
day like, hey, had a lot of fun yesterday, would
you like to hang out again sometime? And she just
responded with that's not how this works.

Speaker 5 (24:53):
That's not how what works.

Speaker 6 (24:55):
I don't well, I don't know what this is.

Speaker 5 (24:57):
Was did you ask her? She meant yeah, I was like, well, not.

Speaker 6 (25:03):
How what works? And she just has not responded at all.

Speaker 4 (25:06):
She doesn't want to get into it.

Speaker 3 (25:07):
She's like, she's like, he's an idiot.

Speaker 8 (25:10):
Yeah.

Speaker 5 (25:11):
Maybe she's like saying that's not how this works, Like
this isn't a romantic situation that's developing here.

Speaker 3 (25:19):
Could I hope yeah, just yeah.

Speaker 5 (25:22):
It depends on how you read it. You could take
it different ways. The only way to know is to
actually reach out to Cassie or she's like, that's how
this works. You need to have a ring buddy with
the target. But okay, so how long has it been.

Speaker 6 (25:37):
It's been a week?

Speaker 3 (25:38):
Okay, okayount of time.

Speaker 5 (25:40):
Yeah, let's reach out to her and find out what
she means and hopefully get you out on another hot
target date with her when we come back to do
your second date update right after this second date update.
If you go out on a date and text them
afterwards asking them out again, they write back, that's not
how they works. What does that mean? You know?

Speaker 3 (26:02):
But when you say it like that, it sounds like
a threat.

Speaker 5 (26:04):
I mean, yeah, it's a mystery. Does it mean you
texted too soon? Does it mean we're not a romantic
thing at all?

Speaker 3 (26:13):
Do you mean that you need to try harder?

Speaker 5 (26:15):
Does it mean you need to read the prologue of
the Da Vinci Code upside down at exactly noon in
the shadow of the Chrysler building and the answer will
reveal itself to you. How did you say, Wow, I'm
just throwing out a guest there. We're hoping to find
out because this one's a little bit different. Jason, our
listener has known the girl whereabout to call, going back years.

(26:36):
They used to work together, asked her out many times
until she finally said yes. The other day at Target,
went out on one date, and afterwards he got that strange,
mysterious text. That's not how this works.

Speaker 1 (26:50):
Yeah, it's interesting because you said you were so nervous,
but she sounds so confident.

Speaker 5 (26:55):
Yeah.

Speaker 6 (26:56):
I mean I felt like I was doing okay because
she was laughing, smiling, and then when she didn't respond,
I was I started questioning everything.

Speaker 1 (27:05):
I didn't call it a date, like she might not
know it's a date.

Speaker 3 (27:09):
Let's get some answers, Jeff, get that Da Vinci codebook out.

Speaker 5 (27:13):
And we're going to be very very clear with her.
We're going to say a romantic date the Hawkeye recently yes,
with lots and lots of kissing, in.

Speaker 3 (27:22):
Action, any of that.

Speaker 5 (27:25):
Well, I'm just saying for the next one, we're going
to make sure it's very clear that he's not in
the friend zone.

Speaker 2 (27:31):
We ask I'm sorry, We're gonna go.

Speaker 5 (27:34):
We're gonna send you out on a romantic hot date.

Speaker 6 (27:37):
Don't scare her. This sounds more awkward than I was
by myself.

Speaker 3 (27:41):
Well, you know this show, Jason.

Speaker 8 (27:43):
Listen.

Speaker 5 (27:43):
We'll try and dial it back just a little bit.
But I'm calling her right now. Hopefully she answers. Here
we go. Hello, Hey, we're We're gonna speak with Cassie.

Speaker 7 (28:01):
This is her.

Speaker 5 (28:03):
Hey, Sorry, sound weird Therehi Cassie, Good morning. This is
a whole radio show. We're called Brook and Jeffrey in
the Morning. Oh my GOSHU Hi, Okay, wait, do you
know the show?

Speaker 7 (28:22):
I kind of like, what is happening?

Speaker 5 (28:25):
Well, this is a second date update. We heard that
you went out recently to drinks with one of our
listeners named Jason. An old I'm not gonna say that
an old coworker.

Speaker 3 (28:39):
Yeah, but why answer like that.

Speaker 7 (28:49):
I feel like that's kind of between him and me.

Speaker 3 (28:52):
Well, he he is clueless, so I don't think anything
is between.

Speaker 7 (28:56):
You and him.

Speaker 5 (28:57):
Yeah, we heard that you guys went out the other day,
and we just want to know how it went from
your perspective.

Speaker 3 (29:03):
Like, were you excited?

Speaker 5 (29:04):
Do you have a good time?

Speaker 6 (29:05):
I mean, like I guess like the date was okay,
But I just.

Speaker 7 (29:10):
Feel like, I don't know, that's just like more of
a me and him thing.

Speaker 6 (29:14):
To talk about.

Speaker 3 (29:16):
What do you mean?

Speaker 5 (29:16):
What is well?

Speaker 7 (29:18):
I've been like putting it off because I don't really
know how to say it to him.

Speaker 1 (29:22):
Oh my god, have you had a crush on him
for years and you finally want to tell him?

Speaker 7 (29:26):
No?

Speaker 5 (29:28):
What I got there's definitely one thing that you were pinpointing,
like there's something that he did wrong. I mean I
think he should now Okay, look, Cassie, I normally don't
do this, and we'd usually find out a little bit
more before I tell you that he's on the phone listening,

(29:48):
but he is. What? Yeah there, Hi?

Speaker 7 (30:01):
What are you doing?

Speaker 5 (30:03):
Uh?

Speaker 6 (30:04):
I don't know. You just haven't said anything for like
six days, I guess, so, like what gives? Why won't
you talk to me?

Speaker 7 (30:16):
I just I didn't appreciate your text?

Speaker 6 (30:19):
What was what was wrong with the text? Did I
say something that was offensive? I just asked if you
wanted to hang out?

Speaker 7 (30:26):
It was just a text, Like, Jason, is that really
all I am to you? Just a text? No call,
not in person, nothing, just a text.

Speaker 1 (30:38):
Uh.

Speaker 6 (30:40):
I mean, I'm sorry, I just I don't know. I
didn't think about going beyond a text, and that's the problem.

Speaker 3 (30:49):
That's what you're supposed to say. No, You're much more
than just a text to me.

Speaker 4 (30:53):
Yeah, I don't want to be clinging it.

Speaker 2 (30:54):
Yes, because I like you too much?

Speaker 6 (30:57):
Yeah? Yeah, I mean did you want me to just
show open at your house after us not seeing each
other for that long? I just thought it would be
the proper way because I wasn't sure, you know, if
you wanted another date.

Speaker 7 (31:11):
But like, I feel like I deserve romance and deserve
more than that, So I don't know.

Speaker 6 (31:18):
Can I ask you again? Then?

Speaker 8 (31:21):
Oh? I like that?

Speaker 7 (31:24):
I don't know, can you Okay.

Speaker 5 (31:32):
No pressure here, Jason, you got this.

Speaker 4 (31:34):
And you may want to wait and ask her later.

Speaker 3 (31:35):
Bro, she wants she wants it now.

Speaker 5 (31:37):
Just deliver a super romantic question. Go ahead.

Speaker 3 (31:40):
Do you have music?

Speaker 5 (31:41):
You got this? I believe.

Speaker 6 (31:43):
Oh, just let me get it out. Just let me
get it out, Cassie. Would you like to go out again?

Speaker 7 (31:49):
Jason? Don't say it like that.

Speaker 3 (31:54):
I mean she set you up. She told you exactly
what she needed. Romance.

Speaker 5 (31:57):
Ye, try it again, Jason, more romantic?

Speaker 6 (32:01):
OKAYSI do you want to go out? With me again, no.

Speaker 2 (32:09):
Information about why you like hers.

Speaker 5 (32:13):
Credit for that?

Speaker 7 (32:17):
Do you hear you? Then it's not do you want?

Speaker 6 (32:21):
What is it? It is because I want to.

Speaker 7 (32:27):
But it's will ill.

Speaker 3 (32:30):
Is just like an English thing where we're getting.

Speaker 6 (32:32):
Okay, if I got to say it exactly with the
words that you want, okay.

Speaker 7 (32:37):
Okay, I don't hear it from your heart.

Speaker 6 (32:40):
Okay, that is from my heart. Like I've just I've
done it so many times. I've asked you, like five times.

Speaker 2 (32:49):
What do you want from this man?

Speaker 1 (32:51):
He told us that he asked you what a dozen
half a dozen times when you work together, and you
turned him down every time.

Speaker 7 (32:57):
Well, I didn't realize it was such a burden for
you to ask me out.

Speaker 4 (33:01):
Jason romantic, but he didn't phrase.

Speaker 5 (33:04):
That very well.

Speaker 3 (33:05):
Know she was this high maintenance. It's a pretty high maintenance.

Speaker 7 (33:09):
Can you just please stay out of our business right now?
Like it's not involving you at all.

Speaker 3 (33:14):
Yeah, you sound like such a pleasure.

Speaker 5 (33:18):
We're supposed to try to make a romantic connection.

Speaker 1 (33:21):
He think Jason sounds like a cool dude, you know,
like he wants to hang out crying.

Speaker 3 (33:25):
He's doing all the things.

Speaker 5 (33:27):
I'm supporting him, Jason, take some of what Brooks said
and use that towards Cassie now.

Speaker 6 (33:33):
As do you want to go out with me? I
want to go out with you a lot, a lot,
a lot. I just want to know if you do.

Speaker 5 (33:42):
That was the best one yet he put some some
more into that emphasis, I'm going to pass.

Speaker 2 (33:49):
Oh my god, you had her past twelve time.

Speaker 5 (33:59):
She just wasn't feeling it. She wasn't feeling it like
he really really meant it, and it was from the heart.
He said that he's.

Speaker 2 (34:05):
Been thinking about her on and off for the last see.
No matter what she was gonna say.

Speaker 5 (34:08):
No, what you should have said is I've been pondering
about you deeply and romantically.

Speaker 8 (34:15):
Love me.

Speaker 7 (34:16):
I think I've definitely had enough of you strangers commenting
on my love life now, so I'm going to hang
up on you now by Oh that's our only hope.

Speaker 5 (34:27):
Yeah, I feel like we should have tried harder to
stop her, but I didn't feel like it. She's EXHAUSTI
h We're getting a lot of texts in at seven eight, five,
nine two saying you actually dodged a bullet by seeing
her again.

Speaker 3 (34:40):
That's say a whole missile.

Speaker 5 (34:45):
Can you think maybe you could let it go now?

Speaker 8 (34:47):
Yeah?

Speaker 6 (34:48):
Well, I definitely don't feel like, uh, I don't think
there's anything I could do with that. I just I
think that there was no possibility and it woul probably
would have been better for her to just say no.

Speaker 8 (34:58):
No.

Speaker 3 (34:59):
That sounded like it was from your heart.

Speaker 5 (35:00):
Yeah, shoo? Should we call her back right now?

Speaker 6 (35:03):
OK?

Speaker 5 (35:04):
Now you're in the.

Speaker 8 (35:04):
Mode brooking Jeffrey in the morning.

Speaker 5 (35:08):
Does Chris Hemsworth ever have to go through crap like this?

Speaker 4 (35:11):
I don't think so.

Speaker 5 (35:12):
I feel like if you're super good looking, that conversation
never comes up. No girl is saying to a hems Worth, O,
can you like ask me out like better and like
like put some actual heart into it?

Speaker 4 (35:23):
Can I get more accent?

Speaker 1 (35:24):
I'm actually pretty sure they just grunts.

Speaker 5 (35:28):
Yes, And God blessed Jason because he tried the question
seven nine different ways whole thing.

Speaker 3 (35:36):
When he gave up, it was almost like she was
messing with him.

Speaker 5 (35:40):
It's not Honestly, I know we're supposed to try to
help facilitate a connection between these people, but we are
all happy that that one did not work out.

Speaker 3 (35:48):
I can't believe he kept trying. Yeah, pick up your dignity. Man,
you can't do this anymore.

Speaker 5 (35:54):
And if you have problems picking up your own dignity,
we can help pick it up for you, at least
a little bit. Yeah, email us, we'll call that person
who's not calling you back. Go check out all of
our second dates wherever you get your podcasts at Broke
and Jeffrey
Advertise With Us

Hosts And Creators

Brooke Fox

Brooke Fox

Jeffrey "Young Jeffrey" Dubow

Jeffrey "Young Jeffrey" Dubow

Alexis Fuller

Alexis Fuller

Jose Bolanos

Jose Bolanos

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