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May 28, 2025 17 mins

One of our listeners is confused after his date ended in the WEIRDEST way ever… but he still has SOME interest. Hear the brand new Second Date Update in the podcast!

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Second date up date. We've been doing these calls for
a while now and found it's not unusual for a
woman to bring one of her friends along with her
on a first date.

Speaker 2 (00:13):
Yeah, I mean it's normally.

Speaker 3 (00:15):
Yeah, normally you tell someone beforehand, they're gonna well tell.

Speaker 2 (00:18):
Me where she sits at the place too.

Speaker 1 (00:21):
Sometimes they're upfront about it and just very open. Sometimes though,
they keep it a secret where they have them hide
somewhere in a nearby booth or inside of a decorative plant,
spying with binoculars to make sure everything's kosher.

Speaker 2 (00:35):
I'm sure you won't get noticed that.

Speaker 1 (00:37):
Yeah. So, yeah, it's a giant plant doing in this McDonald's.
Why is it moving? So we definitely heard that before.
But is it unusual if the friend that she brings
with her is a guy?

Speaker 2 (00:48):
Oh man?

Speaker 1 (00:50):
Apparently that happened to one of our listeners recently. Leo,
is that true your date showed up with another dude?

Speaker 4 (00:58):
Yeah?

Speaker 3 (00:59):
Ok, wow, I mean I have guy best friends like
you know, that could be fine. Did she tell you
beforehand that that was what was going to happen?

Speaker 5 (01:09):
No? No, actually, yeah that was.

Speaker 1 (01:12):
By the way, Brooke has hooked up with almost all
of her guy best friends. So I don't know if
it's a great thing.

Speaker 6 (01:17):
That's because you got to just try it out and
see if that's how you like each other.

Speaker 2 (01:20):
And then you're like, man, that didn't work.

Speaker 1 (01:23):
Friends another target. Run us through how this all happened, Like,
start with how you met her?

Speaker 5 (01:28):
So, like, I met this girl, Christie. I mean it's
this bike club. It's like a group on Facebook and
people get together and we like ride every like a
couple of weekends.

Speaker 4 (01:38):
And I started talking to her.

Speaker 5 (01:40):
Yeah no, it's actually awesome. And I've met a lot
of people, but I met Christy and I just really
liked her.

Speaker 4 (01:45):
And I asked her out.

Speaker 3 (01:46):
Cute What a great way to ask somebody out to
like you already have shared interests.

Speaker 5 (01:51):
Yeah no, and she's amazing and I was so excited.
And I show up and she's there, but she's sitting
at the table with this other guy and she's like, oh, yeah,
this is David. Oh you know a title for David
or distinction like not my brother or my friend or.

Speaker 1 (02:13):
I was the vibe like between them, did you feel
like they had chemistry? Did it feel friendly? Did it
feel sexual? Good question?

Speaker 5 (02:20):
I mean they were definitely really comfortable with each other.

Speaker 3 (02:23):
Okay, this is my first thought is either she is
in a open relationship and thought you maybe knew could
that be it?

Speaker 5 (02:33):
Well, did not get a heads up by any means
on that.

Speaker 1 (02:37):
Okay, okay, and like, don't me wrong.

Speaker 5 (02:39):
Like David's a nice guy, but like there would be
moments where they would just talk with each other or
make obviously like inside Joseph, I.

Speaker 2 (02:47):
You say for the whole, That's what I was gonna ask.

Speaker 5 (02:50):
I paid for the dinner, and it seemed like he
was just part of the package. And I'm still not
sure how to unpack that.

Speaker 1 (03:02):
I think I could see why naturally, You're like, I'm
on a date I offered to.

Speaker 2 (03:06):
Pay of a guy friend.

Speaker 7 (03:08):
Though, to be okay, why would a guy friend want
to sit in on you on a date?

Speaker 3 (03:11):
You know.

Speaker 1 (03:13):
Really could be besties.

Speaker 2 (03:15):
Like my best guys would tell me that's weird.

Speaker 5 (03:17):
I get it that, like women want to make sure
that there's someone around, and like I can understand that,
but I was just so shocked that it was the sky.

Speaker 6 (03:26):
Well yeah, and typically it's like you want security if
it's somebody you've never met before, you've already met this person,
you meet up with them once a month, but during
a bitedown, like, yeah, you should have some before.

Speaker 5 (03:37):
I think I gave a pretty good impression that I'm
not a serial killer, but I respect that boundary.

Speaker 2 (03:45):
The wait, did you ever find out who he was?

Speaker 1 (03:48):
D end No?

Speaker 5 (03:49):
Okay, so we were there for like an hour and
a half. We did flirt, like we all had like
collective conversation.

Speaker 1 (03:54):
Oh so you were flirting with David too. I heard jealous.

Speaker 5 (03:59):
I'm gonna wasn't going to be rude, but it was
so weird that when I left, I sort of just
almost jokingly like reached out and gave them both.

Speaker 1 (04:08):
A group hug.

Speaker 2 (04:11):
Wait you together, Well, they.

Speaker 5 (04:14):
Were going to leave together, so I just hugged them both.
I was like, we should all hang out again sometime.

Speaker 4 (04:23):
And I don't know why the hell I so?

Speaker 1 (04:26):
Well, yeah, because if that is her best even he'll
be like, oh he was a nice guy you hug yeah, or.

Speaker 2 (04:31):
You just friend zoned yourself.

Speaker 1 (04:33):
Yeah, And that's the risk you take when you're on
a triple date. You weren't planning on.

Speaker 2 (04:37):
That's true.

Speaker 1 (04:38):
That so where are we at now with you and Christy?

Speaker 4 (04:42):
Oh?

Speaker 1 (04:43):
Yeah, all right?

Speaker 5 (04:43):
So the way I handled that gets me into this
situation where I'm the one that's not responding and she
has been calling me and texting me, and they want
to know when we should all hang out together.

Speaker 4 (04:56):
And I don't know.

Speaker 5 (04:57):
Why I said it, but now I'm like, I don't
want to hang out with David.

Speaker 1 (05:03):
Yeah, obviously, Well you gave him a hug, like you
basically let him on. She's setting you up with him
right now?

Speaker 2 (05:11):
What do you want us to do?

Speaker 5 (05:13):
My goal is to have a one on one date
with her, so I wanted originally, and I don't know
if that's even possible anymore.

Speaker 1 (05:21):
So you want, with our call here, for us to
surgically remove David from the situation and have it just
be a one on one with you and Christy got
him out of it, Okay, okay, in the most respectful
way possible. We need to figure out how to convince
her to do that.

Speaker 2 (05:37):
You've got to go. I mean nothing on David.

Speaker 5 (05:39):
No, it's cool, dude, but he did.

Speaker 3 (05:41):
I don't want to hang out.

Speaker 4 (05:42):
I don't want to date David.

Speaker 1 (05:43):
Okay, but he's really handsome though, right, no comment? Oh
my god, oh god, because the more handsome he is
the harder this is gonna be. We're gonna find out
when we call Christy and try and get you. Your
second date update coming up right after this hold on
second date update. In the dating world, it can be
hard to get just one person wanting to hang out

(06:05):
with you. But our listener, Leo is a lucky man
who has interests from two people at the same time.
That's the situation. One is his date, Christie. The other
is the random dude that Christy came to the restaurant
with that night named David. Yeah, we can't even say

(06:28):
friend because I guess we didn't get closer. That's the
thing we don't know. Is David her friend, her brother,
her other lover, her stepdad. We don't really know. That
was never made clear the entire night David did and
potentially meant the step dad. It's possible. The thing is,
it's awkward because Christy's been asking if all three of

(06:50):
them can hang out together again, but Leo isn't really
up for that. He wants to cut David out of
the picture, so that's why he's asked us for help.

Speaker 2 (07:00):
You're not David, You're Leo.

Speaker 3 (07:01):
Sorry, this is why I can't juggle more than one
at a time.

Speaker 1 (07:10):
Yeah, you didn't even consider the step dad option, did you.

Speaker 2 (07:16):
I think it's so wild.

Speaker 3 (07:17):
You went through an entire dinner and you still couldn't
figure out how David was connected to your friend Christians.

Speaker 5 (07:24):
I know, like it was awkward and I just didn't
know how to play that.

Speaker 1 (07:30):
Like, so, who were you?

Speaker 4 (07:32):
Get it?

Speaker 2 (07:33):
You're just going with the flow conflict.

Speaker 3 (07:35):
Yeah, yeah, I can't wait to hear how David feels
about the group hug.

Speaker 1 (07:39):
That's right. They did have the three way.

Speaker 2 (07:41):
Hug so she can buy our boy Leo.

Speaker 1 (07:45):
Yeah, out of panic. It sounded like.

Speaker 5 (07:48):
I didn't know what to do. I did panic a little.
It was weird.

Speaker 1 (07:52):
Group hugs are not a bad thing. I think you
handled it.

Speaker 2 (07:56):
Wait for this.

Speaker 1 (07:56):
Call, but we're going to try and help you out.
Just get a date with only Christy. If she's even
up for that, I don't know. It might be her style.

Speaker 2 (08:05):
Is only David an option?

Speaker 1 (08:07):
I think no offense?

Speaker 2 (08:09):
But no, everybody has their own likes.

Speaker 1 (08:13):
Yeah, but Christy might take offense. So let's call her
and see how she feels about it. Hopefully she picks up.
Here we go, Hello, Hey, is this Christy. Yeah, Hey, Christy,
how you doing today? You're on a radio show right

(08:35):
now called Brook and Jeffrey in the Morning.

Speaker 4 (08:40):
Okay, yes, all right, I'm confused.

Speaker 1 (08:42):
But I know it's okay. We're doing a segment right
now call the second Date Update. We're calling on behalf
of one of our listeners and friends of the show
that you went out with recently, named Leo. Yeah, Leo.

Speaker 4 (08:55):
I mean I've been texting Leo.

Speaker 1 (08:58):
Right. We heard a little bit about your hangout, and
I don't know the right way to say this.

Speaker 3 (09:05):
This is different than we normally do. It is different
because we know that you're interested in seeing him again.

Speaker 1 (09:10):
He said that there's been communication about setting up another
hangout between you, Leo, and the other guy that was
there that night, named David.

Speaker 4 (09:21):
It was it was a fun night. I mean it.

Speaker 1 (09:24):
Sounds like totally there's a little bit of a question
mark though around you know, basically, what's going on?

Speaker 2 (09:33):
Why is this so hard?

Speaker 1 (09:33):
Well, it's we're trying to figure out what the dynamic
is between the three of.

Speaker 4 (09:38):
You, right, Okay, Well I'll explain it. But first, like,
do you think there's any way you can like help
me convince Leo to go out with me again. I
mean I really liked him and I kind of liked
me too.

Speaker 1 (09:52):
Like, yeah, yes, with you. I don't think we'll have
any problem getting him to agree to go out with you.

Speaker 2 (09:57):
Honestly, I think it's like sol.

Speaker 1 (10:00):
Problem that Leo has is with the David part.

Speaker 4 (10:04):
No, no, you have to go out with me and David.

Speaker 2 (10:06):
What are you guys like a package or something?

Speaker 1 (10:09):
Why is it so important that it has to be
all three of you going out at once?

Speaker 4 (10:14):
Actually it's more than three of us. There's a fourth.

Speaker 2 (10:18):
What's hold on? Wait?

Speaker 1 (10:20):
Wait wait, there's more a love square.

Speaker 2 (10:23):
Now the guys aren't connected.

Speaker 6 (10:26):
Is it?

Speaker 2 (10:26):
Is it another guy or is it a girl?

Speaker 4 (10:30):
Okay, so it is another guy, but it's not what
you think.

Speaker 1 (10:34):
Yeah, you got to clear this up for us. Christy,
we're really confused because it has to be what we think.

Speaker 4 (10:38):
No, no, it really isn't. Okay. So the third guy,
the fourth person, he was actually filming secretly. He was
filming our date wailing film in the restaurant too. He
was just at another table, kind of pretending he wasn't
doing what he was doing. Why because I am really

(11:01):
doing well on TikTok right now. And there's this trend.
It's called two dates one night.

Speaker 2 (11:06):
Two dates one like a challenge.

Speaker 4 (11:11):
Yeah, two date one night challenge.

Speaker 3 (11:13):
So wait, so you set up a date with David
and set up a date with Leo at the same time,
all for TikTok.

Speaker 4 (11:19):
Yeah, and it's really really well my video. It's like
it's totally going viral.

Speaker 1 (11:24):
Why don't you.

Speaker 3 (11:26):
Guys?

Speaker 2 (11:27):
Why didn't you tell him?

Speaker 4 (11:29):
Because then it wouldn't be changing and everyone would know
what stage.

Speaker 1 (11:33):
So part of the challenge is going on a date
with two guys at the same time and neither of
them knows about it.

Speaker 4 (11:39):
Yeah, but I'm interested in both. I like both.

Speaker 1 (11:41):
So wait, that is on the comments section. They must
be voting for who they liked the moment.

Speaker 4 (11:45):
My god, exactly, there's so many people voting.

Speaker 3 (11:51):
Are you some like wizard that you're able to get
these two guys to stay?

Speaker 1 (11:56):
Yeah, be careful, your jealousy is showing.

Speaker 2 (11:59):
I think it's crazy.

Speaker 3 (12:00):
You must be like so lovely and like such a personable,
charismatic person and convinced two dudes to hang around.

Speaker 4 (12:08):
Why don't about that? But I'm not that looking.

Speaker 7 (12:12):
Everyone had a fun night, they said, Yeah, I don't
know if Leo is having as much fun though listening
and hearing all of this, because Christy, you should know
Leo is on the phone right now.

Speaker 3 (12:24):
But she's not.

Speaker 1 (12:26):
Job Well, we're recording this for our podcast.

Speaker 4 (12:30):
Ruinedtok Okay, I'm sorry.

Speaker 1 (12:33):
I apologize for that, but Leo, man, are you still there.

Speaker 5 (12:38):
I'm just trying to process what I just heard. I
didn't know what to expect. It was weird to begin with,
but this was like, I'm honestly weirdly impressed in a way.

Speaker 3 (12:52):
But okay, I feel like I went through the same
emotions and she's impressed.

Speaker 5 (12:57):
To all the social media, yes, but I do like you.

Speaker 1 (13:03):
She likes that you get her lots of views, that's
for sure. Social experience.

Speaker 3 (13:06):
I mean, what were you going to do at the
second date with Leo and David?

Speaker 1 (13:10):
Again, that's the best thing to have a part two
of your video, But like, was that going to be
the big reveal?

Speaker 2 (13:16):
Was that when you were going to tell.

Speaker 4 (13:17):
Him, oh, I was going to do a sequel first obviously?

Speaker 1 (13:21):
Yeah, yeah, she was going to reveal at the double
marriage when they're both on the altar at the same time.
By the way, guys, they talk.

Speaker 2 (13:29):
They still don't know who each other are.

Speaker 1 (13:33):
Who will show up at the wedding. We'll see you
when the door's open. Yeah. If I'm Leo, I would
question whether or not your feelings were valid.

Speaker 4 (13:40):
That's fair. But we did go on a date. It
was a good time, and I do like him, Oh
my god.

Speaker 2 (13:45):
Yeah.

Speaker 3 (13:46):
But if the tables were turned and you showed up
to a dude and he had another girl sitting there.

Speaker 4 (13:50):
That's different. I mean, it's different when you're a girl.

Speaker 1 (13:53):
Yeah, because she's hot, Brooke. Remember that's probably every other
rule in the book. So, Leo, you've been listening here,
You've kind of heard what Christy has to say. Do
you believe her?

Speaker 5 (14:05):
I don't think. If I don't believe you, I don't
understand what or why you would do it, Leo.

Speaker 1 (14:15):
All of social media is hard to understand why things
are the way that they are and why things get popular.
It doesn't make any sense.

Speaker 3 (14:22):
This feels like explaining any TikTok trend to Jeffy Exactly.

Speaker 1 (14:26):
It's just crazy and weird and people want to watch it.
So we would like to arrange that second meetup if
you're still open to it, Leo, for one place.

Speaker 2 (14:35):
Wait, why are we asking him?

Speaker 1 (14:37):
Well, things have changed because now that Leo knows more
about the whole situation and the motives. I think it's
only fair, since he's our listener, to get the okay
from him first.

Speaker 2 (14:47):
Oh I can't.

Speaker 1 (14:50):
Well, let's find out. So Leo, I'm just going to
go ahead and ask you, would you be willing to
go out again with Christy or Christy and David or
maybe just David. There's options, Jeff.

Speaker 2 (15:01):
I mean, there's a lot of different ways you can work.
I don't forget about him.

Speaker 1 (15:05):
There's any interest on the other.

Speaker 5 (15:07):
Side that's not going to work, not for me?

Speaker 4 (15:10):
No, okay, Okay, Well, I mean I'm a little disappointed,
and I don't want this to sound weird. It's kind
of awkward. But do you know anyone that looks.

Speaker 7 (15:20):
Like you wait for the video and I'm really doing well.

Speaker 2 (15:26):
You can't trick the Leo fans.

Speaker 5 (15:29):
You're crazy? Who does that?

Speaker 4 (15:32):
I'm crazy. I'll be crazy famous pretty soon. So you
missed out, oh man.

Speaker 2 (15:38):
Famous and infamous are two different things, Leo.

Speaker 1 (15:40):
You're going to look back at this call as the
moment that both of your ones got away.

Speaker 2 (15:46):
That doesn't add to it too, right.

Speaker 1 (15:47):
I don't know how it works either.

Speaker 4 (15:50):
David does, though.

Speaker 1 (15:54):
I would watch that TikTok video for sure.

Speaker 6 (15:56):
Freaking Jeffrey in the morning, Well that was unexpected.

Speaker 2 (16:01):
Wow.

Speaker 3 (16:01):
Yeah, Like I feel like there's so many other options
that would have been better.

Speaker 2 (16:06):
Yeah, better answers.

Speaker 1 (16:07):
Couldn't have predicted the two dates, one night TikTok challenge.

Speaker 2 (16:11):
And where's David. Where's David's outrage at this? Is he
just going along with it? You know?

Speaker 1 (16:16):
I think exactly. Maybe he appreciates all the fame that
he's getting from TikTok.

Speaker 3 (16:20):
I feel I think he's out there wondering who the
hell Leo is.

Speaker 1 (16:23):
Maybe that's possible. Also, I'm kind of offended that none
of us have been involved in a two dates, one
night TikTok challenge. Where is our invites to be in one?

Speaker 2 (16:33):
You can d m Jeff You don't, ye, Jeff?

Speaker 1 (16:38):
Oh yeah, I should go check out the four you
page and see if I'm on. But look, I understand
Leo's stance. It's just sometimes I think you need to
put your standards and your self respect to the side.

Speaker 2 (16:49):
Should have got.

Speaker 1 (16:50):
In the name of social media infamy. It's a small
price to pay.

Speaker 3 (16:56):
Yeah, says the guy who barely posts a picture of
his dogs.

Speaker 1 (16:59):
Exactly. You could be famous online right now and you
wouldn't know. I could be famous, but I don't feel
like it right now.

Speaker 2 (17:05):
That's what it is.

Speaker 1 (17:05):
That's where I stay. I'll be there one day though. Yeah,
and you could be in a nice throttle or maybe
in just like a one on one relationship if that's
what you want. Yeah, whatever you want exactly, email the show.
We'll call that person who's not calling you back. And
go check out all of our Second Day podcasts wherever
you get yours at Brook and Jeffrey
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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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