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November 25, 2025 18 mins

Is it ever okay for a person to meddle in their friends love life? It doesn’t matter because we’re doing it anyway before one listener's friend can go on a blind date!

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Episode Transcript

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Speaker 1 (00:01):
It happens in movies and reality TV shows all the time,
people meddling in the dating lives of their other friends.
Oh yeah, in all the time. You know, is it
okay to do that? Because if it is? And Brook,
after this is over, Alexis says she has some thoughts
on your current situationship with the guy that you live with.

Speaker 2 (00:23):
It just if you're open to them.

Speaker 3 (00:24):
It's a marriage.

Speaker 1 (00:26):
Yeah, okay, but Brook's life aside. We are about to
do some love life meddling today because one of our
listeners swears she has a really, really good reason. She
needs to stop her close friend from going out on
a blind date, and she wants our help to block it.

Speaker 3 (00:50):
I don't know.

Speaker 1 (00:50):
I know you're skeptical, but you might be on her
side when you hear why in a brand new awkward
Tuesday phone call.

Speaker 4 (00:57):
Next awkward It's Tuesday. It's awkward Tuesday phone call.

Speaker 1 (01:05):
As an adult going out with high schoolers, bad idea,
It's terrible idea. Get word, That's what I said. Bad idea?
So DoD Chalantley though, what about going out with people
you knew from back when you were in high school?
Is that okay?

Speaker 5 (01:25):
Is totally different?

Speaker 1 (01:25):
Well, one of our listeners, Carrie says, absolutely not. What terrible,
horrible idea to date your old high school class mate.
Apparently that's why she needs our help today, Carrie, Welcome
to the show.

Speaker 6 (01:39):
Hi thinks sounds like high.

Speaker 1 (01:40):
School drama is still following you right into adulthood.

Speaker 6 (01:43):
Huh yeah, it's weird. And let me just let me
just specify. I'm not opposed to other people dating people
that they knew in high school, but not my friend Justin.

Speaker 5 (01:54):
Oh, just Justin. So it's not even other people from
your high school, it's just justin you.

Speaker 1 (01:59):
This is that's a special case. What's going on with Justin?

Speaker 7 (02:03):
Okay?

Speaker 6 (02:03):
So just and our friends, we've been friends, like you said,
since high school. We're now in our late twenties.

Speaker 5 (02:08):
Okay.

Speaker 6 (02:09):
And the other day he told me, Hey, I'm going
on a date. It's crazy. You can't even imagine who
I'm going to date with. And it turns out to
be this girl we knew in high school, Catalina Leena.

Speaker 1 (02:28):
I don't know anything matters. What's with Catalina?

Speaker 6 (02:31):
Well, she was the awkward girl. She was like kind
of like science geeky, a little.

Speaker 5 (02:36):
Still bullying, the awkward girl in high school. Are we
over that?

Speaker 6 (02:40):
Oh no, no, no, no, Like she knew she was awkward.
She was like the awkward smart science ye girl, Listen,
I was a little awkward. It's just I was able
to play it off better than she was.

Speaker 1 (02:50):
May Brooke, You must have had somebody at your school
who was like that at handling their mess and that
was the awkward.

Speaker 5 (02:57):
Yes, why are you better at chemistry? That was our
chemistry class? Right?

Speaker 1 (03:02):
Yeah, So that's bad news that your friend might be
going out with your awkward kid from high school.

Speaker 6 (03:10):
Well, I'm going to give you a little more backstory
before I tell you why that's bad. Okay, he got
hooked up through another friend of ours from high school
who was connected.

Speaker 8 (03:19):
She had a crush on him from high school.

Speaker 6 (03:21):
Blah blah blah blah. So they like got each other's
phone numbers. We're talking. He still has no clue what
she looks like. No one could find her on social media.
I was curious, and I discovered that her parents got
divorced and she took her mom's maiden name. So I
found her on social media under her maiden name.

Speaker 5 (03:42):
Okay, snooping, So why are you doing all this work?

Speaker 1 (03:46):
He's just going down on.

Speaker 6 (03:47):
A date because she's gorgeous. I mean, she's like Scarlet Johansson, Britain's.

Speaker 1 (03:52):
Met It's amazing. Why is it bad? Yeah?

Speaker 6 (03:57):
Generally that is great for her. I'm happy for her,
are you? But here's the thing, guys, I don't want
him to know, but I'm I kind of have a
thing for Justin.

Speaker 8 (04:10):
It we've known each other for so long.

Speaker 6 (04:12):
It just a few years ago started and I'm not
ready for him to know. I need more time. But
if he gets put in front of this girl, I
have no chance.

Speaker 1 (04:26):
This is why it was good being nerdier in high school,
because she actually has probably a cool personality too.

Speaker 5 (04:32):
Oh, they're not helping, Jose. I mean you sounded petty,
and I get why you're jealous, and you admit it.
That all makes sense now.

Speaker 6 (04:39):
Yeah, I just I don't think I could compete.

Speaker 1 (04:41):
Okay, you don't want Justin going out with the now
pretty girl? Is Justin the type of guy that's into
pretty women?

Speaker 6 (04:47):
Or is there any guy that's not into pretty women?

Speaker 1 (04:51):
Yeah?

Speaker 6 (04:52):
Sorry, no, please, I'd prefer an ugly, stupid woman.

Speaker 5 (04:56):
So wait, what do you want to do though? Do
you just finally want to tell him how you feel
before he goes out with her.

Speaker 6 (05:02):
No, I'm not ready for that. I need more time.
But I just need to figure out to convince him
not to go out with her.

Speaker 5 (05:10):
Oh oh, you could just stay in this like not zone,
but I have a crush.

Speaker 1 (05:14):
Yeah, I mean this is tricky, Like alexis, what do
you think about this situation, trying to stop your friend
from going out with somebody hotter. I don't know if.

Speaker 9 (05:23):
It's the nicest thing to do, but I would do
it probably myself too.

Speaker 6 (05:27):
Yeah, but what did you just tell the guy that
you like him?

Speaker 1 (05:31):
Yeah, like, you're you're.

Speaker 5 (05:32):
In your late twenties at this point.

Speaker 1 (05:34):
You got to shoot your shot. How many decades have
you been waiting? Maybe she's waiting till he gets married
and then divorced, so that his confidence is so low
he'll settle for anything. That could be a good strategy.

Speaker 5 (05:46):
Yeah, what if he likes you too, and you guys
are both just living in this world of not telling
each other.

Speaker 6 (05:51):
Well, I haven't. I mean that's kind of why I
feel like I need a little more time, Like I
haven't really tried to look for the signals and.

Speaker 1 (05:58):
Stuff like that, Like lighting the fire. Now you realize
he's not going to be single.

Speaker 5 (06:02):
I would fully like him until he found somebody hotter
and smarter.

Speaker 10 (06:08):
Yeah, listen, let me say like he stated other girls,
and this is going to make me sound really superficial,
but they didn't feel like competition to me, and so
I don't think that I really realized it until like
a woman came along that would totally blow me out
of the water.

Speaker 8 (06:25):
Now I wouldn't have a chance.

Speaker 1 (06:27):
Okay, now the gloves are coming off this.

Speaker 5 (06:32):
What do you want our help doing?

Speaker 7 (06:33):
Then?

Speaker 5 (06:34):
Like, are we calling Justin and telling him not to
go out with her?

Speaker 7 (06:37):
Yeah?

Speaker 6 (06:37):
Yeah, this is convincing Justin not to go out with her,
telling him that you like him exactly.

Speaker 1 (06:44):
Okay, chances that's all our job to come up with
a way to convince Justin to cancel his date with
the now gorgeous looking Catalina without letting her know that
she's gorgeous.

Speaker 6 (06:59):
Okay, And you don't have to keep rubbing in how
gorgeous she is. I get that, I obviously know what
I've seen her.

Speaker 1 (07:05):
Okay. I don't think you.

Speaker 5 (07:06):
Can be named Catalina without being absolutely dropped gorgeous.

Speaker 1 (07:11):
She's not gorgeous. She's just stunning, and we're going to
convince Justin to not go out with her. We'll give
us a little bit of advice and let you make
your awkward Tuesday phone call right after this.

Speaker 4 (07:24):
It's awkward, It's Tuesday. It's awkward Tuesday phone call.

Speaker 1 (07:29):
If you're just joining us for this awkward Tuesday phone call,
it's a story that really speaks to my soul. The
awkward kid in high school who was maybe a little shy,
did school plays and chess club, and during field trips
he would crawl underneath the seats on the bus and
then pop up from below and say, guess who. They

(07:49):
were completely undateable back then, but a few years ago
by and now they've matured mentally and physically.

Speaker 5 (08:00):
I feel like you still do that thing, Rail, and that.

Speaker 1 (08:04):
Ugly duckling has grown into an undeniable, bubbling cauldron of
raw desires. Because it's undeniable. Listener, Carrie, she's not that person.
She's actually kind of threatened by that person. That's why
she wants our help to stop her friend Justin from

(08:25):
going out with the awkward girl from high school who's
now blossomed into the female me, why why did you
want to Jeff? Because I mean, secretly she does have
some feelings for Justin, but isn't ready to tell him that. Carrie,
your goal is to convince him to not go out with.

Speaker 6 (08:42):
Her, right, yeah, exactly?

Speaker 8 (08:44):
All right?

Speaker 1 (08:45):
But how are we gonna do that? I think Jose
has an idea for you. Yeah. So look, we kind
of want him to just naturally not like her anymore
and pass up on the date. We have to do
the old fashioned high school trick is start a rumor
about her because you know what's that?

Speaker 9 (09:01):
I heard she made out with her brother and it
wasn't that long ago, are you?

Speaker 1 (09:06):
That's what I brother's review of the kids was not
good your words.

Speaker 6 (09:16):
I mean, I think it would be effective, but that's
the little.

Speaker 1 (09:20):
Means that's gross. You're gonna have to play a little
bit dirty to get what you want. What do you think, bro? Okay, listen,
I don't think it's about.

Speaker 5 (09:29):
Putting the hot girl down. I think it's about building
him up.

Speaker 1 (09:33):
He doesn't even know this girl is hot.

Speaker 5 (09:34):
All you need to say is, listen, you are so hot,
You're so beyond blind dates, like, yes, so above that.

Speaker 2 (09:41):
Then you tell.

Speaker 5 (09:42):
Him I have the most gorgeous friend ever that I
have to set you up with. She's funny, she's everything
you've ever been looking for. Like that, I can't tell
you who it is.

Speaker 1 (09:52):
It's Brookes with your guy.

Speaker 5 (09:56):
O God, more competition, and then you drop it on
him later when you're ready that the mysterious perfect woman
is you.

Speaker 11 (10:05):
Oh wow?

Speaker 6 (10:11):
I'm like, what if I meet him at a restaurant.
I'm the one that walks in and I have to
deal with the potential rejection of him being like, what
are you doing here?

Speaker 5 (10:20):
All guy friends want to sleep with their girlfriends.

Speaker 1 (10:25):
There's Brooks advice, just sleep around. All right, Let's just
give him a call and we're gonna let you make
your awkward Tuesday phone call and try and convince him
not to go out on his date. We're we're here
for you, all right, We're down the number right now?

Speaker 6 (10:42):
Okay, good luck?

Speaker 7 (10:50):
Hello? Hey, how's it going? Hey?

Speaker 1 (10:54):
Care?

Speaker 10 (10:54):
Bara?

Speaker 7 (10:55):
What's going on? Not much?

Speaker 6 (10:57):
How are you doing?

Speaker 7 (10:59):
I'm just killing some time before I have to go
to work. What's up?

Speaker 5 (11:03):
Oh?

Speaker 11 (11:04):
You know, I just wanted the chat.

Speaker 7 (11:05):
Say hey, oh, did.

Speaker 8 (11:07):
Billy get a hold of you?

Speaker 7 (11:09):
Yeah? I assume you're talking about the blind date that
I mentioned the other day.

Speaker 11 (11:15):
No, no, no, I just.

Speaker 8 (11:16):
Meant about hanging out next weekend.

Speaker 7 (11:19):
Oh yeah, we're gonna say now.

Speaker 8 (11:20):
That you mention it, are you Are you still doing that?
You're still going to hang out?

Speaker 7 (11:25):
I mean, I'm very I'm very curious. I mean, he
mentioned that Catalina's doing all kinds of neat things right now,
and I don't know, I just figured, what the hell? Yeah,
that's cool.

Speaker 8 (11:37):
You know, this is kind of weird. But I kind
of heard something really random recently about her, like a.

Speaker 7 (11:41):
Rumor, a rumor. What are you doing about?

Speaker 6 (11:47):
Okay? So I heard that she was at a party
like a month ago and kind of mete out with
her brother.

Speaker 7 (11:55):
What where did you hear this?

Speaker 8 (12:00):
Yeah, I don't know, just randomly.

Speaker 2 (12:04):
Randomly what Yeah, I don't know, But like, blind needs
are really weird, aren't they.

Speaker 8 (12:10):
Like are you sure you really want to a blind date?
I mean, you're so cool and like you're good looking,
and you really want to like go through the awkwardness
of a blind date and all that.

Speaker 7 (12:22):
Well, I mean it's just a blind date. I'm not
going to marry the girl. Just figured made up for
a cup of coffee then just talk, you know, you
know what, how about this?

Speaker 8 (12:31):
Like, I have a friend, she's awesome, she's.

Speaker 6 (12:34):
Great, she's super hot.

Speaker 8 (12:36):
What have I set you up with her?

Speaker 7 (12:38):
Instead? You you want to set me up on a
blind date?

Speaker 8 (12:43):
No, it's not a blind date because I've seen her
and I know her well.

Speaker 11 (12:46):
But like Helen, and no one has seen her, none
of us is like talk to her in a long time.
I mean, I guess you guys have been texting. That's something,
but like, you know, I don't know, this might be better.

Speaker 7 (13:00):
Will tell me about this friend of yours.

Speaker 8 (13:04):
I mean, she was great, you know, like you would.
I think you really like her. She's you would totally
get along. I know you guys have a lot in common.

Speaker 6 (13:12):
And I know one hundred percent that she does not
make out with her brother at party.

Speaker 7 (13:20):
I firmly hope.

Speaker 1 (13:20):
Not laughing too hard? Hey, Justin, Hey, Justin.

Speaker 7 (13:33):
What are you at a party or something? What's all
that laughter?

Speaker 1 (13:40):
I think we're kind of a party. We're we're a
morning radio show. Justin called Brook and Jeffrey in the Morning.
Why did you go with those days advice?

Speaker 7 (13:48):
I thought that was solid though, kidding, but I am
so lost right now.

Speaker 1 (13:55):
You're on the radio right now, man, Okay, we're doing
a segment on an awkward Tuesday phone call. Carrie reached
out wanting a little bit of help to talk to
you about your upcoming blind date with this girl. We're
not so sure it's a good idea for you to.

Speaker 7 (14:11):
Go out with her because of the brother thing or
I mean, that's.

Speaker 1 (14:16):
Just one of many, many.

Speaker 5 (14:17):
Reasons, because Carrie does have someone really cool that she
wants to set you up with.

Speaker 7 (14:24):
Kerry. What exactly is going on here? This is is
a little weird.

Speaker 6 (14:28):
Okay, listen, justin, I I haven't been super honest with you.

Speaker 8 (14:33):
I have not been the best friend in the sense
that I discovered Katalina's.

Speaker 7 (14:40):
Social media and well you found her social media. What
does she look like?

Speaker 1 (14:48):
That sound is probably all you need to know. Just
new rumor coming in. I hear she looks like Oscar
the Groudy, like a muppet whatever. Who cares what she
looks like. You're not the type of guy that bases
a relation ship on looks, are you?

Speaker 7 (15:01):
Just Like I said, at the very least, we would
just get a cup of coffee and catch up a
little bit. That doesn't mean we go on the second
date or anything.

Speaker 1 (15:09):
Yeah, it starts with coffee drinking. Next thing, you know,
brothers are kissing.

Speaker 6 (15:13):
Okay, I don't feel.

Speaker 8 (15:15):
Like any of this is helping you guys.

Speaker 4 (15:18):
Did you need to do the thing?

Speaker 1 (15:20):
I mean?

Speaker 6 (15:20):
Okay, Okay, I think this has become too much of
an awkward quagmire for me not to say the thing
that I have been trying to not say. Say the thing?

Speaker 1 (15:31):
Carrie, what thing?

Speaker 7 (15:32):
What? I still don't know what the hell is going
on here?

Speaker 2 (15:38):
We have such a good connection, and I just kind
of wondering if, like, maybe there's a mutual attraction beyond
friendship between us?

Speaker 1 (15:49):
Is m what do you think?

Speaker 7 (15:52):
So you dragged me through a whole radio show to
finally spill the beams here?

Speaker 1 (15:59):
Maybe she was nervous.

Speaker 8 (16:01):
Obviously, I realize now this is not the right way
to do it. I just I just thought it.

Speaker 6 (16:07):
Like maybe we needed some more organic time to let
it evolve. But then I saw Katalina and I would
have no chance if you met her.

Speaker 1 (16:17):
That is not true.

Speaker 5 (16:19):
Justin don't you think that Carrie is amazing? Could you
see something more between you two?

Speaker 7 (16:24):
Have you ever picked I wouldn't have been friends with her?
For the last decade. If I didn't think she was
amazing you We've talked about this. You always you know,
undersell yourself, see and to be perfectly honest, Yeah, I
think you kind of went about this the wrong way.
Is so finally getting this out in the open. But hey,
might make a great story for our first date.

Speaker 1 (16:45):
So justin you're into the idea of maybe going out
with Carrie here, not a friend date, like a romantic date.

Speaker 7 (16:52):
I wouldn't mind one bit.

Speaker 1 (16:54):
Yeah.

Speaker 5 (16:56):
Really it sounds justin like you have liked her for
a long time.

Speaker 7 (17:00):
To be probably be honest, I have.

Speaker 1 (17:02):
Yeah, Oh my god.

Speaker 7 (17:04):
I was afraid that I was in the zone. But
you know, I just kind of I just you know,
like you said, we've been friends for a long time.
I didn't know how you felt, so I didn't want
to like ruin a good thing.

Speaker 8 (17:13):
But we've yeah, both kind of been.

Speaker 1 (17:18):
Idiots in all of our years.

Speaker 7 (17:20):
Here.

Speaker 1 (17:21):
I never thought Brooks advice of just sleep with all
of your friends what's the worst happen would actually work
a good job, bro A. You gonna find out.

Speaker 7 (17:34):
Brook and Jeffrey in the morning.

Speaker 5 (17:36):
Actually, I think that one was really cute.

Speaker 1 (17:38):
Yeah, we were I an update from them.

Speaker 9 (17:41):
I mean a lot of drama to just ask someone
out that you've known for a long Yeah.

Speaker 6 (17:46):
It's true.

Speaker 11 (17:47):
Was just telling your closest friend, hey, I have a crush.

Speaker 1 (17:49):
On you, or crossing the borders hard?

Speaker 5 (17:52):
Can I kiss you?

Speaker 6 (17:53):
That's what I'm straight for.

Speaker 4 (17:55):
Yeah, straight for it after ten years of friendship.

Speaker 3 (17:59):
No, yeah, Bill, But the first time I kissed one
of my best friends, oh this is I was like sixteen, right,
and it was like my second kiss I'd ever had,
and the first one went horribly wrong.

Speaker 5 (18:12):
So this one was really.

Speaker 9 (18:13):
Good and I got so excited I high five him afterwards.
Oh and he was like, she goes Brooke, don't ever
do that again.

Speaker 1 (18:25):
You're close enough he could tell you that.

Speaker 6 (18:27):
Yeah.

Speaker 5 (18:27):
Yeah, he's still one of my best buddies.

Speaker 1 (18:29):
Yeah, so a couple.

Speaker 5 (18:32):
I think what I think what this is is if
you have a crush, just tell him all right, there's
nothing yeah.

Speaker 3 (18:39):
Friendship and then when that backfires, call us okay and
we'll do it.

Speaker 5 (18:43):
Another awkward Tuesday for you. Or you can always submit
on our website at Brookingjeffrey dot com and always follow
us on socials at BRIC 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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