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May 28, 2025 18 mins

One of our listeners is confused after his date ended in the WEIRDEST way ever… but he still has SOME interest, so it couldn’t be that bad. 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):
All right, brand new Second Date podcast for you today,

(00:02):
and it is Brook and Jeffrey in the morning.

Speaker 2 (00:04):
It is bonkers to me.

Speaker 1 (00:06):
Okay, you show up to a date and there's another
person there besides the person you're going on the date with.

Speaker 2 (00:12):
Do you stay or do you go?

Speaker 3 (00:14):
I ask questions, yes, questions.

Speaker 2 (00:17):
Well, it depends.

Speaker 1 (00:18):
If it's another guy, maybe I stay and see who's hotter,
but if you if it's.

Speaker 2 (00:22):
A girl, yeah, this is a wild one.

Speaker 1 (00:27):
I can't wait to read the comments after this to
see where people stand on this issue. But let us
know right now, alexis what are you seeing in the comments?

Speaker 4 (00:34):
Yeah?

Speaker 2 (00:34):
Speaking of comments, I feel like they've been extra good lately.

Speaker 1 (00:36):
Yes, it's good, but there you are just really leaving
some funny one people putting effort in.

Speaker 2 (00:41):
Yes, and Rebecca Miller said, my son and I love
listening to y'all.

Speaker 1 (00:45):
He's six and every time we get in the car
he has to listen to Booger and Jeffrey.

Speaker 2 (00:51):
I'm officially changing my name.

Speaker 3 (00:55):
It is so good.

Speaker 2 (00:57):
Here's your second Date. Remember enjoy and hit that like
and subscribe.

Speaker 3 (01:00):
How much for being here The Second Date update. 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 (01:14):
Yeah, I mean it's normally.

Speaker 1 (01:16):
Yeah, normally you tell someone beforehand, they're gonna well tell
me where she sits at the place too.

Speaker 3 (01:22):
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,
spye with binoculars to make sure everything's kosher.

Speaker 2 (01:36):
I'm sure you won't get noticed that.

Speaker 3 (01:38):
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 (01:50):
Oh man?

Speaker 3 (01:51):
Apparently that happened to one of our listeners recently, Leo,
Is that true your date showed up with another dude? Yeah?

Speaker 2 (02:02):
I mean I have guy best friends like you know.
That could be fine.

Speaker 1 (02:07):
Did she tell you beforehand that that was what was
going to happen?

Speaker 5 (02:10):
No? No, actually yeah that was.

Speaker 3 (02:13):
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 1 (02:18):
That's because you got to just try it out and
see if that's how you like each other.

Speaker 2 (02:22):
And then you're like, nah, that didn't work.

Speaker 3 (02:24):
Friends the target run us through how this all happened,
Like start with how you met her?

Speaker 5 (02:30):
So, like, I met this girl, Christie I'm in. 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. And I started talking to her. Yeah no,
it's actually awesome. And I've met a lot of people,
but I met Christy and I just really liked her
and I asked her out.

Speaker 1 (02:47):
Cute What a great way to ask somebody out to
like you already have shared interests.

Speaker 4 (02:52):
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.

Speaker 5 (03:02):
Like, oh, yeah, this is David. Oh you know a
title for David or distinction like not my brother or
my friend.

Speaker 1 (03:10):
Or my or.

Speaker 3 (03:15):
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 (03:21):
I mean they were definitely really comfortable with each other.

Speaker 1 (03:24):
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 (03:35):
Well, did not get a heads up by any means
on that?

Speaker 4 (03:38):
Okay, okay, and like, don't me wrong, Like.

Speaker 5 (03:40):
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.

Speaker 2 (03:47):
I you stayed for the whole That's what I was
gonna ask.

Speaker 5 (03:51):
I paid for the dinner, and it seemed like he
was just part of the package.

Speaker 6 (04:00):
And I'm still not sure how to unpack that.

Speaker 3 (04:03):
I think I could see why naturally, You're like, I'm
on a date. I offered to pay.

Speaker 2 (04:09):
Of a guy friend. Though, to be okay, why would
a guy friend want to sit in on.

Speaker 1 (04:12):
You on a date?

Speaker 3 (04:13):
You know, I really could be besties.

Speaker 2 (04:17):
My best guy friend would tell me that's weird.

Speaker 5 (04:18):
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 1 (04:27):
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 before.

Speaker 5 (04:38):
I think I gave a pretty good impression that I'm
not a serial killer, but I respect that boundary.

Speaker 2 (04:46):
Wait did you ever find out who he was?

Speaker 1 (04:49):
End?

Speaker 5 (04:50):
No?

Speaker 6 (04:50):
Okay, so we were there for like an hour and
a half.

Speaker 5 (04:52):
We did flirt, like we all had like collective conversation.

Speaker 3 (04:55):
Oh so you were flirting with David too? Not just jealous.

Speaker 5 (05:00):
I mean, I wasn't gonna be rude, but it was
so weird that when I left, I I sort of
just almost jokingly like reached out and gave them both.

Speaker 3 (05:09):
A group hug.

Speaker 5 (05:12):
Wait you together, Well, they were going to leave together,
so I just hugged them both. I was like, we
should all hang out again sometime. And I don't know
why the hell I so?

Speaker 1 (05:27):
Well, yeah, because if that is her best even he'll
be like, oh he was a nice guy you hug.

Speaker 2 (05:31):
Yeah, or you just friend zoned yourself.

Speaker 3 (05:34):
Yeah, that's the risk you take when you're on a
triple date you weren't planning on.

Speaker 2 (05:38):
That's true.

Speaker 3 (05:39):
That's so where are we at now with you and Christy?

Speaker 5 (05:44):
Oh yeah? All right, So the way I handled that
gets me.

Speaker 4 (05:46):
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 5 (05:57):
And I don't know why I said it, but now
I'm like, I really don't want to hang out with David.

Speaker 3 (06:04):
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 (06:12):
What do you want us to do?

Speaker 5 (06:14):
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 3 (06:22):
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.

Speaker 5 (06:32):
Him out of it, Okay, Okay.

Speaker 3 (06:34):
In the most respectful way possible. We need to figure
out how to convince her to do that.

Speaker 2 (06:38):
You've got to go. I mean nothing on David.

Speaker 5 (06:40):
No, it's cool, dude, but he did. I don't want
to hang out.

Speaker 6 (06:43):
I don't want to date David.

Speaker 3 (06:44):
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
the second update. In the dating world, it can be
hard to get just one person wanting to hang out

(07:06):
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

(07:30):
friend because I guess we didn't get closer. That's the
thing we don't know. Is David her friend, her brother,
her lover, her stepdad. We don't really know. That was
never made clear the entire night. David did and potentially
meant the stepdad. It's possible. The thing is, it's awkward
because Christy's been asking if all three of them can

(07:51):
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 (08:01):
David, you're Leo. Sorry, This is why I can't juggle
more than one at a time.

Speaker 5 (08:11):
Yeah, you didn't even consider the step dad option.

Speaker 6 (08:16):
Did you?

Speaker 2 (08:17):
I think it's so wild.

Speaker 1 (08:18):
You went through an entire dinner and you still couldn't
figure out how David was connected to your friend Christians.

Speaker 5 (08:25):
I know, like it was awkward and I just didn't
know how.

Speaker 4 (08:29):
To play that.

Speaker 2 (08:31):
Like, so who were you.

Speaker 6 (08:34):
Get it?

Speaker 2 (08:34):
You're just going with the flow conflict.

Speaker 1 (08:36):
Yeah, yeah, I can't wait to hear how David feels
about the group hug.

Speaker 3 (08:40):
That's right. They did have the three way hug.

Speaker 2 (08:43):
So there she can buy our boy leo.

Speaker 3 (08:46):
Yeah, out of panic. It sounded like.

Speaker 5 (08:49):
I didn't know what to do.

Speaker 4 (08:50):
I did panic a little. It was weird.

Speaker 2 (08:53):
Group hugs are.

Speaker 3 (08:54):
Not a bad thing. Yeah, I think you handled it.
Wait for this call, but we're going to try and
help you out, just to get a date with only Christy.
If she's even up for that, I don't know. It
might be her style.

Speaker 2 (09:06):
Is only David an option?

Speaker 5 (09:08):
No? I don't think no offense but no.

Speaker 2 (09:13):
Everybody has their own likes.

Speaker 3 (09:14):
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?

Speaker 6 (09:31):
Yeah?

Speaker 3 (09:32):
Hey Christy? How you doing today? You're on a radio
show right now called Brook and Jeffrey in the Morning.

Speaker 6 (09:41):
Okay, yes, all right, I'm confused, but.

Speaker 3 (09:44):
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.

Speaker 5 (09:55):
Yeah, Leo.

Speaker 6 (09:56):
I mean I've been texting Leo.

Speaker 4 (10:00):
Right.

Speaker 3 (10:01):
We heard a little bit about your hangout, and I
don't know the right way to say that.

Speaker 1 (10:06):
This is different than we normally do. It is different
because we know that you're interested in seeing him again.

Speaker 3 (10:11):
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 6 (10:22):
It was a it was a fun night.

Speaker 3 (10:24):
I mean it sounds like totally there's a little bit
of a question mark though around you know, basically, what's
going on?

Speaker 2 (10:34):
Why is this so hard?

Speaker 3 (10:35):
Well, it's we're trying to figure out what the dynamic
is between the three of you, right, Okay.

Speaker 6 (10:43):
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 thought you.

Speaker 3 (10:52):
Liked me too, 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 (10:58):
Honestly, I think it's like sold.

Speaker 3 (11:00):
The problem that Leo has is with the David part.

Speaker 6 (11:05):
No, no, you have to go out with me and David.

Speaker 2 (11:08):
What are you guys like a package or something?

Speaker 3 (11:10):
Why is it so important that it has to be
all three of you going out at once.

Speaker 6 (11:15):
Actually it's more than three of us.

Speaker 3 (11:18):
There's a fourth what hold on, wait wait wait, there's
more a love square.

Speaker 2 (11:24):
Now connect the guys aren't connected?

Speaker 1 (11:27):
Is it?

Speaker 2 (11:28):
Is it another guy or is it a girl?

Speaker 6 (11:31):
Okay, so it is another guy, but it's not what
you think.

Speaker 3 (11:35):
Yeah, you got to clear this up for us. Christy,
we're really confused because it has to be what we think.

Speaker 6 (11:40):
No, no, it really isn't. Okay. So the third guy,
the fourth person, he was actually filming secretly. He was
filming our data 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 doing

(12:02):
well on TikTok right now. And there's this trend. It's
called two dates one night.

Speaker 2 (12:07):
Two dates one like a challenge.

Speaker 6 (12:12):
Yeah, two date, one night challenge.

Speaker 1 (12:14):
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 6 (12:20):
Yeah, and it's really really well my video. It's like
it's totally going viral.

Speaker 2 (12:25):
Why don't you.

Speaker 3 (12:28):
Guys?

Speaker 2 (12:28):
Why didn't you tell him?

Speaker 6 (12:30):
Because then it wouldn't be changing and everyone would know
what stage.

Speaker 3 (12:35):
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 6 (12:40):
Yeah, but I'm interested in both. I like both.

Speaker 3 (12:42):
So wait, that is on the comments section. They must
be voting for who they liked the moment.

Speaker 6 (12:46):
My god, exactly, there's so many people voting.

Speaker 1 (12:52):
Are you some like wizard that you're able to get
these two guys to stay?

Speaker 3 (12:57):
Yeah, be careful, your jealousy is showing. I think that's crazy.

Speaker 1 (13:02):
You must be like so lovely and like such a personable,
charismatic person and convinced two dudes to hang around.

Speaker 6 (13:10):
Why don't about that? But I'm not that looking.

Speaker 7 (13:13):
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, but.

Speaker 2 (13:26):
She's not daping down.

Speaker 3 (13:28):
Well, we're recording this for our podcast.

Speaker 6 (13:31):
Rutok Okay, I'm sorry.

Speaker 3 (13:34):
I apologize for that, but Leo, man, are you still there.

Speaker 5 (13:39):
I'm just trying to process what I just heard.

Speaker 4 (13:45):
I didn't know what to expect.

Speaker 5 (13:46):
It was weird to begin with, but this was like,
I'm honestly weirdly impressed in a way.

Speaker 1 (13:53):
But okay, I feel like I went through the same
emotions and she's impressed to all us.

Speaker 5 (14:00):
Social media thing, yes, but I do like you.

Speaker 3 (14:04):
She likes that you get her lots of views, that's
for sure. Social experience.

Speaker 1 (14:08):
I mean, what were you going to do at the
second date with Leo and David?

Speaker 3 (14:11):
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 (14:18):
Was that when you were going to tell him.

Speaker 6 (14:19):
Oh, I was going to do a sequel first? Obviously?

Speaker 3 (14:22):
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 (14:30):
They still don't know who each other are.

Speaker 4 (14:34):
Who will show up at the wedding.

Speaker 3 (14:35):
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 6 (14:42):
That's fair. But we did go on a date. It
was a good time, and I do like him.

Speaker 2 (14:46):
Oh my god.

Speaker 4 (14:47):
Yeah.

Speaker 1 (14:47):
But if the tables were turned and you showed up
to a dude and he had another girl sitting there.

Speaker 6 (14:51):
That's different. I mean it's different when you're a girl.

Speaker 3 (14:54):
Yeah, because she's hot, broke. Remember that's probably every other
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 (15:06):
I don't think If I don't believe you, I don't understand.

Speaker 4 (15:12):
What this is or why you would do.

Speaker 6 (15:15):
It, Leo.

Speaker 3 (15:16):
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 1 (15:24):
This feels like explaining any TikTok trend to Jeffy exactly.

Speaker 3 (15:27):
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.

Speaker 4 (15:36):
For one place.

Speaker 2 (15:37):
Wait, why are we asking.

Speaker 3 (15:38):
Him 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 (15:48):
Oh I can't believe.

Speaker 3 (15:51):
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
just David.

Speaker 4 (16:00):
Come on, there's options, Jeff.

Speaker 2 (16:02):
I mean, there's a lot of different ways you can work.
I don't forget about him.

Speaker 3 (16:06):
There's any interest on the other side.

Speaker 5 (16:09):
That's not going to work, not for me.

Speaker 6 (16:12):
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 like
you wait for the video and I'm really doing well.

Speaker 2 (16:27):
You can't trick the Leo fans.

Speaker 4 (16:30):
You're crazy? Who does that?

Speaker 6 (16:34):
I'm crazy. I'll be crazy famous pretty soon. So you
missed out, Oh man.

Speaker 2 (16:39):
Famous and infamous are two different things, Leo.

Speaker 3 (16:41):
You're going to look back at this call as the
moment that both of your ones got away.

Speaker 2 (16:47):
That doesn't add to it too, right, I don't know
how it works either.

Speaker 5 (16:51):
David does, though.

Speaker 3 (16:55):
I would watch that TikTok video for sure.

Speaker 2 (16:58):
Freaking Jeffrey in the morning.

Speaker 3 (17:00):
Well that was unexpected.

Speaker 2 (17:02):
Wow.

Speaker 1 (17:03):
Yeah, Like I feel like there's so many other options
that would have been better.

Speaker 3 (17:07):
Yeah, better answers couldn't have predicted the two dates, one
night TikTok challenge.

Speaker 2 (17:13):
And where's David. Where's David's outrage at this? Is he
just going along with does you know? I think exactly?

Speaker 3 (17:19):
Maybe he appreciates all the fame that he's getting from TikTok.
I feel I.

Speaker 2 (17:23):
Think he's out there wondering who the hell Leo is.

Speaker 3 (17:25):
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 (17:34):
You can d M Jeff Jeff.

Speaker 3 (17:39):
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.
Got in the name of social media infamy. It's a
small price to pay.

Speaker 1 (17:57):
Yeah, says the guy who barely posts a picture of
his dog exactly.

Speaker 3 (18:01):
Jeff, you could be famous online right now and you
wouldn't know. I could be famous, but I don't feel
like it right there.

Speaker 2 (18:06):
That's what it is.

Speaker 3 (18:07):
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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Brooke Fox

Brooke Fox

Jeffrey "Young Jeffrey" Dubow

Jeffrey "Young Jeffrey" Dubow

Jose Bolanos

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Alexis Fuller

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