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August 18, 2025 17 mins

The guy on the phone today probably couldn’t have picked a more embarrassing way to end his date even if he tried!

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Speaker 1 (00:00):
Second date updated. I'm not sure if you guys remember this,
but about six months ago we did an awkward Tuesday
phone call with a listener named Kevin who wanted to
ask out his coworker and he was super nervous about
it needed our advice. The call wasn't perfect, he had
some stumbles along the way. But she's sound like every

(00:25):
call that we do, absolutely flawless.

Speaker 2 (00:27):
I'm tried to remember what happened.

Speaker 1 (00:30):
In the end, she did say yes and agree to
a date with him. I guess I don't know. It
was a yes bottom line. Now, apparently they went out
a few times, things fizzled, didn't quite last. So Kevin
has jumped back into the beautiful oasis we call the
modern dating pool. And again, that was months ago. So, Kevin,
how's it been. Have you had a lot of dates

(00:52):
in that time?

Speaker 3 (00:54):
Like ten, ten, ten days?

Speaker 1 (00:57):
You dates in the last two years?

Speaker 2 (00:58):
Why are you doing some work? Congratulations? You're a catch?

Speaker 3 (01:02):
Yeah, but I actually haven't had a second date.

Speaker 2 (01:06):
But is that from your choosing? Like maybe you didn't
want to go out again with any of them?

Speaker 3 (01:12):
No, I would have been happy to go out with
really any of them again.

Speaker 1 (01:16):
Oh, okay, Okay, that's hard.

Speaker 2 (01:22):
You're here, We're going to help you.

Speaker 3 (01:23):
Yeah, they haven't been the greatest. I actually had a
really bad one. Yeah she was a nice girl, I thought,
But when I walked her out to her cards opened
the door, and then she just suck her punched me,
and then drove off.

Speaker 1 (01:37):
Wait what did you say?

Speaker 3 (01:40):
Sorry?

Speaker 1 (01:41):
I did not expect that sentence.

Speaker 2 (01:42):
That is terrible face? Did she punch you in the face?

Speaker 3 (01:46):
It was actually in the back of my head. I
was opening her door, and then all of a sudden,
I just felt.

Speaker 1 (01:52):
This, like, did you ask permission to open the door
for her? Because she mayn't really have not liked that
you weren't fast enough for her.

Speaker 3 (02:00):
Maybe so, I don't know if she thought I was
going to kiss her or.

Speaker 1 (02:04):
Your head, how are you going to kiss her? Maybe
she thought that you were trying to steal her car.

Speaker 3 (02:10):
So.

Speaker 2 (02:12):
It has to be a self defense.

Speaker 1 (02:13):
He's not like, give me the keys.

Speaker 3 (02:19):
I don't know. Wasn't that bad? I don't know.

Speaker 1 (02:22):
Some people give off natural grand theft daughter vibes, so
maybe you fell into that category.

Speaker 2 (02:27):
Ask for you? Okay?

Speaker 1 (02:29):
Now I am yeah, concu so a sucker punch girl?
The one you want us to call for a second
date update, we'll call her. Well, who do you want
to call?

Speaker 3 (02:42):
I've had this really bad luck until I met Chelsea.

Speaker 1 (02:46):
Chelsea, Okay, it's a new girl.

Speaker 2 (02:48):
Okay, no physical violence.

Speaker 1 (02:50):
I hope you'll tell us about your I'm assuming you
went on a date with Chelsea.

Speaker 3 (02:53):
Yeah, she didn't punch me.

Speaker 1 (02:56):
Actually perfect, we're improving.

Speaker 3 (02:58):
I thought it was a good sign, and we connected
the best out of all of the first dates I
went on.

Speaker 2 (03:04):
Okay, well what made what made it the best?

Speaker 4 (03:07):
Felt like I could talk to her because like when
we went on our coffee date, it was a good conversation,
even though it didn't last very long. Okay, it was
actually like twenty minutes.

Speaker 2 (03:20):
Why was it so short?

Speaker 3 (03:21):
You know, I'm not really sure my friends got by
and by your friend? Yeah, I don't really know why.

Speaker 1 (03:29):
Okay, So you had a friend come by randomly and
you talk to the friend a little bit, and you
feel like maybe she got offended that the attention was
taken away from her.

Speaker 3 (03:38):
I make I don't know. That would be weird to me.

Speaker 1 (03:41):
She got a friend in what.

Speaker 2 (03:43):
Happens if you're only there for twenty minutes and you
have a five minute conversation with a friend. That's one
fourth of the date.

Speaker 1 (03:49):
They learned trying to play it off. Hey, Brooke, good
to see you here.

Speaker 2 (03:52):
Yeah, I'm too successful and beautiful.

Speaker 1 (03:56):
I feel like I normally wouldn't ask this, but I
feel like I need to know Chelsea. She's not the barista, right,
you're not considering that a date. That's creative? Like she
doesn't work there.

Speaker 3 (04:07):
No, she doesn't work there.

Speaker 1 (04:09):
Okay, that's a good question. How did it end? Yeah,
after the twenty minutes, how did you two leave it?

Speaker 3 (04:15):
She said she had to do something, so we got
up and left. And I guess that was kind of
weird too, because I was kind of like behind her
for a couple of blocks.

Speaker 1 (04:23):
She walked away the same direction.

Speaker 2 (04:28):
That's like the most awkward thing ever.

Speaker 1 (04:31):
And then she started to jog, and then you started
to jog. You're like, hey, I'm gonna run out of someone.
Weird chases you.

Speaker 3 (04:39):
I end up I lost her, I lost you, I think, Yeah.

Speaker 2 (04:45):
That's really Did she know you were back there?

Speaker 3 (04:48):
I don't think so. I don't know.

Speaker 1 (04:50):
Okay, but you weren't following her. That was just a coincidence.
You had the same route home.

Speaker 2 (04:54):
Dude, I hate that even when that happens with my
friends were saying goodbye at the restaurant and then we're like.

Speaker 1 (04:59):
Yeah, get it, you get it all right? So how
long has it been since this twenty minute date?

Speaker 3 (05:07):
I credit two weeks?

Speaker 2 (05:09):
Two weeks?

Speaker 3 (05:09):
Okay?

Speaker 2 (05:11):
I have you reached out much with her?

Speaker 3 (05:13):
I was texting her quite a bit?

Speaker 2 (05:16):
Yeah, we may, said, yeah, we might.

Speaker 1 (05:20):
We may find out if you've crossed any lines or
how many texts you've actually sent when we call her here.
I think it's more how far he did cross them,
or maybe they were right in that sweet spot. We
don't know, Brooke. Remember when you said you had hope.

Speaker 2 (05:34):
Yeah, I do have hope as long as you didn't
send her a picture of the back of her head
as she was walking away from you on this He
was just.

Speaker 1 (05:42):
Trying to make sure she doesn't get sucker punched back there.

Speaker 3 (05:44):
What did I was gonna say when I was on
last time, Brooke? You told me to be more certain,
So I'm really trying to be here.

Speaker 2 (05:52):
Yeahies in their car, there's a balance that we need
to discuss.

Speaker 1 (05:58):
But maybe when enough period and weren't trying to be weird.
You were just trying to walk to your car.

Speaker 2 (06:03):
And maybe that's not why she's not calling me back
at all.

Speaker 1 (06:06):
We're making stuff. Okay, well let's call her and use
that assertion to aggressively get you a second date. When
we called Chelsea right after this hold on second date update,
don't you hate it when you're on a first date
and the girl says she has to go and you
accidentally follow her all the way home. No, jef, I
think it was.

Speaker 2 (06:26):
Only three blocks, to be fair, I mean enough blocks
to be alarming.

Speaker 1 (06:30):
Yeah, but you lost her. That's what happened to our listener, Kevin.
Sort of. He wasn't following his date Chelsea on purpose.
They just left the coffee shop at the same time,
and he coincidentally was walking behind her on the street
for a long, long while.

Speaker 2 (06:45):
I mean, yeah, at any point, did you think I
should take a different route.

Speaker 1 (06:50):
Or just stop for a second? No, stop, hope, He
didn't think speed up, catch up with her. Did that
thought come to your mind at all, Kevin, any of those?

Speaker 3 (06:59):
Yeah, I didn't think it was that weird, and so
I've been thinking about it, like while we were on hold,
and I think you should tell her that I didn't
intentionally walk behind her because I really did it.

Speaker 2 (07:11):
Okay, so you want you want us to let her know.

Speaker 1 (07:13):
That, Okay, yeah, okay, okay. We're not exactly sure what
happened there. We just know that the date was only
twenty minutes long, which is kind of short to get
to know someone. That's honestly the bigger concern for me,
like why did she only stay for twenty minutes? The
following is a totally different story. If you were in
a hurry, why would you even schedule a date during
that time?

Speaker 2 (07:32):
They were just trying to squeeze it in and it's
like one of those pre dates where it's just like
a quick coffee, like will this be worth a full night?

Speaker 1 (07:39):
You didn't catfish her with like a photo of Liam Hemsworth,
did you, because you do sound like a Liam to
me right now? Kind of hunky.

Speaker 3 (07:46):
I'm actually bushing right now. But now does a.

Speaker 1 (07:50):
Name could have fooled me? Let's call Chelsea here. We'll
see if we can get an explanation from her. If
she picks up all right, here we go. Hello, Hey,
is this Chelsea?

Speaker 5 (08:09):
This is who's calling?

Speaker 1 (08:10):
This is a radio show calling called Brook and Jeffrey
in the morning.

Speaker 5 (08:13):
Hey, Chelsea, Uh what what what is this?

Speaker 1 (08:19):
This is fun for some of us, it's fun. It's
a segment we do call the Second Date Update. And
we're looking at sorry.

Speaker 2 (08:28):
Okay, just listening, just actively listening.

Speaker 1 (08:32):
By interrupting me. But let's okay. We're trying to help
out one of our listeners that you went out on
a date with recently. He says he had a really
good time with you, but it ended kind of short.
His name is Kevin.

Speaker 2 (08:47):
Okay, I'm hoping that was a smile and not a laugh.

Speaker 1 (08:50):
Yeah.

Speaker 2 (08:51):
Sensitive.

Speaker 1 (08:52):
We're calling because Kevin told us a little bit about
your guys' date coffee date, coffee date, and from what
we heard, it sounded pretty fun.

Speaker 2 (09:00):
Tame short.

Speaker 5 (09:02):
That was two weeks ago.

Speaker 2 (09:04):
Yeah, but he he liked you, He thought you were awesome.
He wanted to see you again.

Speaker 1 (09:08):
He said he's been pursuing it actually and texting you,
trying to organize something, but he doesn't understand why nothing's happening.

Speaker 5 (09:17):
Yeah, he has sent me quite a few texts, but
I guess I'm confused as to why he doesn't understand
why he start moving forward.

Speaker 2 (09:25):
Did you write him back he. I mean, I guess
we never asked if you ever texted him back.

Speaker 5 (09:31):
From my perspective, he was pretty obviously.

Speaker 1 (09:36):
The only idea that he had about the date, about
why it would have ended so quickly, is he did
mention one of his friends stopped by and said.

Speaker 3 (09:44):
Hi, that's what he said.

Speaker 5 (09:47):
He he said, a friend stopped by.

Speaker 1 (09:50):
Yeah, like that.

Speaker 2 (09:53):
You think that they weren't actually friends?

Speaker 5 (09:55):
Was it his ex? No? I mean, as far as
I know, I don't think it was an ex, but
I don't know. Thirty seconds a minute into us meeting
at the coffee shop, this guy comes over and sits
like right next to us, isn't looking at me at all.
So I asked Kevin. I was like, Hi, can we

(10:15):
introduce him? He's like, well, no, no, don't. He's not engaging
in the conversation. He's just my emotional support friend.

Speaker 1 (10:24):
Emotional support friend.

Speaker 5 (10:26):
So originally I thought he might have been kidding, and
so I laugh and he's like, it's not funny. This
is Charles. I've had a couple of poor dates, and
Charles is really there to just kind of help me
with my confidence and communicate more effectively. I mean, I

(10:50):
think if maybe I had been given a heads up,
I would have been more.

Speaker 3 (10:55):
Open to the idea.

Speaker 1 (10:59):
Emotional support friend.

Speaker 2 (11:00):
Vest Dude, that's amazing that he can find a friend
that will take the time to go on a day
with him. I mean, but I'll say I think that
that says a lot about Vin that he must.

Speaker 1 (11:10):
Be a good I need to know is Charles sitting
on his phone?

Speaker 2 (11:12):
Is he's just listening.

Speaker 1 (11:15):
We got the impression that he just popped in real
quick and left.

Speaker 3 (11:19):
No, not at all.

Speaker 5 (11:20):
He was there the whole time. He wasn't really engaging
in the conversation. He was just there.

Speaker 2 (11:26):
Did he hype Kevin up ever? You know, like he's.

Speaker 1 (11:32):
Sport?

Speaker 5 (11:33):
I mean he laughed at some of the things that
Kevin said, but beyond that, there wasn't much in her action.

Speaker 2 (11:39):
Everybody needs a backup friend, Charles a few tables over.

Speaker 1 (11:43):
Yeah, we didn't know that was how it played out.
We got a little bit of a different version of
that story.

Speaker 2 (11:49):
Charles is on the phone too.

Speaker 1 (11:51):
Yeah, because oh my god, we have an emotional support
friend quietly listening on the other line right now, just
to make sure that I do a good job with
this segment. And that person is Kevin.

Speaker 2 (12:01):
Kevin's here.

Speaker 5 (12:03):
What he's on the phone.

Speaker 1 (12:04):
Yeah, he's really Actually he wants to talk in this conversation,
so I'm going to give him permission to jump in
and say something.

Speaker 2 (12:11):
Okay, if he's there, Keviny there, Yeah, I'm here. How
you doing, buddy, I'm good.

Speaker 3 (12:18):
I'm just I'm listening. Yeah, I don't understand what the
big deal is, really, Kevin.

Speaker 1 (12:27):
When did you get an emotional support bro? You didn't
tell us about that? Well?

Speaker 3 (12:32):
Yeah, I mean a friend is a friend. He doesn't
need like a title or.

Speaker 1 (12:36):
You sounds like you gave him a title. You you
called him your emotional support friend.

Speaker 2 (12:41):
Kevin, you brought him along on the date and didn't
tell us the whole time.

Speaker 3 (12:45):
I mean, yes, he was there, but he was there
for me.

Speaker 1 (12:49):
Sure, Chelsea, do you see where he's coming from?

Speaker 5 (12:54):
I guess. I mean, but you kind of have to
put my like yourself in my shoes, Kevin. It's it's
a little bizarre to just have a third person there
without kind of giving the heads up why and not
engaging really in the conversation.

Speaker 3 (13:09):
Yeah, are you mad because he didn't laugh at your
jokes and he has.

Speaker 1 (13:16):
I'd be mad that's a good question, guys, Chelsea, No,
not really.

Speaker 5 (13:22):
I don't think I was particularly funny because I was
kind of creeped out by the whole thing.

Speaker 1 (13:28):
I told so many jokes and just I.

Speaker 2 (13:33):
Kevin, do you think that maybe you could have told
her prior to the date that he was coming along.

Speaker 1 (13:38):
Yeah, he's going to be right.

Speaker 3 (13:39):
I didn't need to tell her because he wasn't going
to do anything. Like he's just the wallpaper. He's going
to be there now for me.

Speaker 1 (13:48):
So what I think, Kevin, Chelsea is saying that it's
hard for her to connect romantically with you.

Speaker 5 (13:55):
I don't even mean romantically, I just mean as a
person to persons. Just it's hard.

Speaker 1 (14:01):
Yeah, Kevin, it's a little bit distracting, Kevin.

Speaker 5 (14:05):
Maybe he's waiting for Charles to responds.

Speaker 1 (14:09):
Charles speak up right now?

Speaker 3 (14:12):
Okay, so it's a little bit distracting, I guess. But
like the thing is, I can tell him to do
whatever I want. Does that make sense because I'm the
one that's paying him?

Speaker 1 (14:26):
Oh you paying.

Speaker 3 (14:31):
Hard? I mean okay, yeah, he was technically not facing
you for the time, But I mean I could guess
I could get him to like face the wall if
you really wanted.

Speaker 1 (14:45):
Well, I do think that would be better. That's that's
at least a good first step. Can we agree on that?
Awkward Kevin, I mean, people need to tell him we
left the rest of the day. But the blindfolded a
ball game, you can't see, you can't speak, can bear
ald of you.

Speaker 2 (15:01):
Emotional support is totally normal and needed. But let's get
you a dog or you know, yeah, but dogs can't
laugh at jokes exactly.

Speaker 3 (15:11):
And it was a good date.

Speaker 2 (15:13):
It wasn't, did.

Speaker 5 (15:14):
You hear it wasn't a good date. I am so sorry, y'all.
I don't understand why this was even a conversation. It
is awkward and weird, and I've got to go. I
hope you all have a great day.

Speaker 1 (15:25):
Sounds like you need an emotional support friend to deal
with that.

Speaker 3 (15:30):
She keeps having to go, and I think that's.

Speaker 2 (15:34):
She's not interested. And I don't know that you're going
to find many that are interested when Charles has to
be there with you. But a dog, a lot of
women would be interested.

Speaker 3 (15:42):
Yeah, emotional for animals are kind of weird. I prefer people.

Speaker 1 (15:48):
Okay, okay, well maybe again, maybe just follow her home
again and see if she STOPOK Jeffrey in the morning. Man,
I don't say this about many people, but this show
is an open door for Kevin whenever he wants to
come back. He is officially a friend of the show,
even if he wasn't being one hundred per century full

(16:09):
with us about his emotional support friend. I like him
and I would let him follow me home anytime.

Speaker 2 (16:15):
Is he the only one that pushes back on dogs
that people are better than dogs? They're not Kevin.

Speaker 1 (16:21):
People are your problem. Yeah, everybody agrees. All the people
on the textboard. They're saying dogs.

Speaker 2 (16:26):
Are better than be yes, get the right emotional support.

Speaker 1 (16:30):
Actually, wait, did his emotional support friend follow Chelsea home too?

Speaker 2 (16:36):
So there's two dudes following If there's.

Speaker 1 (16:38):
Two guys following you, now I kind of understand the creepiness,
especially when he's talking to his friend and going, what
is the boy?

Speaker 2 (16:46):
You didn't understand the creepiness when the guy was sitting
next to him staring at her.

Speaker 1 (16:50):
The date itself was pretty honest. Yeah, I mean he's
just being supportive. No better ways, yeah, better way you
should have done a FaceTime totally.

Speaker 2 (17:01):
Yeah, I mean he honestly could have had him on
speakerphone and just set the phone on the tab.

Speaker 1 (17:06):
You know, there's lots of life lessons to be taken
from these segments, and you can go find them online
wherever you get your podcast at Brook and Jeffrey and
then email the show. We can call that person who
wasn't calling you back

Speaker 2 (17:17):
Brook and Jeffrey in the morning.
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