June 24, 2025 • 17 mins
One of our listeners has a looming conversation coming up and it’s one of the most difficult things you could ever talk about with a loved one. Before it happens they want our help via an Awkward Tuesday Phone Call!
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Episode Transcript
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Speaker 1 (00:01):
What's the toughest conversation that you could ever have with
your significant other?
Speaker 2 (00:07):
Break up?
Speaker 3 (00:08):
Good thing? I don't have one, Jeff.
Speaker 1 (00:09):
Well, I mean the first one would probably be it's
not yours, the second one is it mine?
Speaker 3 (00:22):
It's yours, and it has to be.
Speaker 2 (00:23):
Well, if you're a guy, maybe you wouldn't know. But
it's a weird question to ask.
Speaker 1 (00:31):
But maybe more important than any of those, is are
you going to finish that.
Speaker 3 (00:38):
Question?
Speaker 2 (00:40):
Wow, that was an extra gas.
Speaker 3 (00:44):
Oxygen mask.
Speaker 4 (00:44):
Well, you can believe it.
Speaker 1 (00:46):
One of our listeners has a looming conversation even more
cringe than all of those combined. It's about to happen
with his longtime girlfriend. You're going to hear what it
is and see if we can help him out in
your awkward to day phone call.
Speaker 4 (01:01):
Next, It's awkward.
Speaker 2 (01:04):
It's Tuesday.
Speaker 5 (01:05):
It's awkward Tuesday phone call.
Speaker 1 (01:08):
On this segment, we've helped listeners tackle all sorts of
big pivotal moments in their love lives. We've helped people
ask somebody out, We've helped somebody propose before even help
someone on where to install the swing?
Speaker 4 (01:24):
What room is it going to fit best in?
Speaker 2 (01:27):
I don't remember that segment.
Speaker 6 (01:28):
I do.
Speaker 1 (01:29):
I'm just saying we've been there for all of our
listeners through all of their struggles, but today, I don't
think we've ever dealt with this particular issue in a
relationship before. It might be one of the biggest conversations
a couple could have. But good news is I've got
two of the best aes around.
Speaker 2 (01:48):
Advice experts always be selling.
Speaker 1 (01:55):
They're waiting to hear from Drew. So, Drew, welcome to
the show. How can we help you not screw up
your relationship?
Speaker 7 (02:02):
What's up? Guys? So? Yeah, I definitely need some help here, Okay.
Speaker 2 (02:06):
Can we start with who the relationship is with?
Speaker 7 (02:09):
Sure? So her name is Kelsey?
Speaker 2 (02:10):
Okay, okay?
Speaker 4 (02:11):
And do you already have a swing installed? Is that
what this is?
Speaker 7 (02:15):
We're not there yet, but we're talking about it.
Speaker 4 (02:18):
Call back when you need help with that. But what
are you dealing with now?
Speaker 7 (02:21):
So? I've been dating Kelsey now for the last couple
of years, so it's kind of serious.
Speaker 2 (02:25):
Yeah you guys, do you guys live together?
Speaker 7 (02:28):
No? No, not yet?
Speaker 1 (02:29):
Okay, Okay, tell us a little bit more about Kelsey.
Speaker 4 (02:32):
Who is she?
Speaker 7 (02:33):
So? She's this great, amazing woman, so much in common
she loves camping, She drives a jeep. She's like just
super old fashioned. She doesn't have social media, which I
love it. I think it's refreshing, it's new, it's great.
Speaker 4 (02:48):
Good. She's a different type of gal totally.
Speaker 7 (02:50):
I met her because I'm in real estate. So I
was showing houses one day and she came in looking
for property with some friends.
Speaker 8 (02:56):
And Okay, so she's got money too, right, I mean
she's successful.
Speaker 7 (03:00):
She's looking at her Yeah. Yeah, So we have this
great relationship.
Speaker 4 (03:05):
Okay, what's the problem.
Speaker 1 (03:07):
Why why did you email us for help with this great, amazing,
perfect relationship with this jeep driving woman.
Speaker 7 (03:13):
Well, so it's why I need you guys help because
it's really like kind of a sensitive thing. So I
was at the point after the one year mark where
I wanted her to move in with me.
Speaker 4 (03:21):
Okay, that's big.
Speaker 7 (03:24):
I asked her and straight up said, would you move
in with me? She goes, no, Okay, oh I was expecting.
Speaker 2 (03:31):
Yeah, you were not expecting that.
Speaker 7 (03:33):
No.
Speaker 1 (03:35):
Why would he ask that if he thought that she
might say no by this point.
Speaker 4 (03:39):
They would have the conversation.
Speaker 8 (03:41):
It sounds like you didn't have a Yeah, he didn't
have a conversation prior to asking, and that was the
issue that trying to.
Speaker 4 (03:47):
Start or maybe the place that you live kind of sucks.
Speaker 7 (03:50):
Well, she's explained. She gave me the reason she doesn't
want to live with a guy before she's married.
Speaker 4 (03:55):
Oh you know, I you can see that.
Speaker 8 (04:00):
Oh yeah, I didn't live with anybody until I met
my husband because it's so complicated.
Speaker 2 (04:04):
You know, then you're like combining.
Speaker 4 (04:06):
What are you talking about? You with your husband before
you were married to you know, when.
Speaker 2 (04:09):
I married him, he's the only guy I ever list.
Speaker 4 (04:11):
This is what she's saying. She doesn't want to live
with anyone until she is married.
Speaker 7 (04:15):
I mean, she doesn't necessarily want it to be after.
She just wants like a solid commitment that makes sense.
Speaker 8 (04:21):
Yea, Like by the time I moved in with my husband,
I knew this was the person I was going to
be with for the rest of my life.
Speaker 2 (04:27):
Oh like I just knew that.
Speaker 1 (04:29):
So she wants something that says that marriage is going
to be in the books. Like I'm assuming that's where
the conversation led to.
Speaker 7 (04:37):
Basically, Yeah, I mean we talked about it. We didn't
dive too deep into it. Again, like out of the blue,
he goes, I'll even sign a prenup, which I was
not even expecting.
Speaker 1 (04:47):
Whoa, whoa, that's like even more serious than marriage.
Speaker 2 (04:51):
Can you do that before you're married? I have no idea.
I don't have a breed up. I have no idea.
I mean I could see where you.
Speaker 8 (04:57):
Would want some sort of like is it because she's
worried about combining your stuff or saying I have.
Speaker 3 (05:03):
Money like we were talking about and she doesn't want
you to take it.
Speaker 7 (05:06):
Well, I kind of have the money. I mean, I
own a bunch of property and she knows that. So
that's why she said that.
Speaker 3 (05:15):
So she's saying it's not about the money. She loves
you for you.
Speaker 7 (05:18):
Yeah, And the problem is now it never feels like
the right time to tell her that I've already met
with the lawyer and I've already had these papers already
drawn up and all that, because I've done that and
I'm ready for.
Speaker 5 (05:30):
This next set with lawyers, and he's he's drawn up
the prenup to secure his assets before he asks her
hand in marriage.
Speaker 4 (05:38):
That's so romantic.
Speaker 3 (05:39):
It is so you have to get down one knee
and say, will you take this pen and document?
Speaker 2 (05:49):
Right, I'm your idea.
Speaker 8 (05:50):
Well, she mentioned, but it sounds like you guys didn't
have a lot of conversations.
Speaker 2 (05:54):
So where are you at right now with everything?
Speaker 5 (05:55):
Yeah?
Speaker 3 (05:56):
Good question.
Speaker 7 (05:57):
So I want to mention it before I pose, not after.
You know what I mean, and I need help bringing
it up. You know it's not.
Speaker 1 (06:04):
Weird, Okay, So you want our help to let her
know that there is a prenup ready for her to
sign whenever she wants, and then after that then we'll
start the engagements and serious commitments that she's always wanted.
Speaker 7 (06:18):
Yeah, okay, why didn't you?
Speaker 1 (06:20):
Okay, So I mean if if she was the one
who brought it up and it's her idea, then what
are you worried about?
Speaker 2 (06:26):
Why didn't you just tell her? I don't understand that,
Like I.
Speaker 7 (06:29):
Don't because it's not a it's a very sensitive topic
when it comes to money and assets. I feel a
little strange about having that discussion, to be honest, Well.
Speaker 5 (06:37):
And even could have been not joking, but she could
have just been throwing it out there and not been
like actually serious and like wait, you actually drew up
the documents.
Speaker 3 (06:46):
That's another level.
Speaker 2 (06:47):
Just feel like it'd be a red flag to me,
but I don't know.
Speaker 1 (06:50):
I think it's a very romantic move. I don't know why,
just trying to kill the NaNs in this segment, was you.
Speaker 3 (06:57):
Lawyered up before you?
Speaker 2 (06:58):
I'm pretty anti preno?
Speaker 4 (07:00):
Yeah, well know what, We're going to go to work
here for you, Okay, Drew.
Speaker 1 (07:03):
We're going to find out the most romantic, over the
top way to tell somebody. I have a prenup ready
for you to sign.
Speaker 7 (07:13):
I appreciate that I need help with your so much.
Speaker 2 (07:14):
You could like dot your eyes with a heart.
Speaker 4 (07:18):
The ideas are already flowing.
Speaker 1 (07:20):
We're gonna start your happily ever after when we do
your awkward Tuesday phone call right after this.
Speaker 4 (07:27):
It's awkward.
Speaker 2 (07:28):
It's Tuesday.
Speaker 4 (07:30):
It's awkward Tuesday phone call.
Speaker 1 (07:32):
I think we need to clarify something here before we
move on. Because the listener on the phone, Drew asked
his girlfriend to.
Speaker 4 (07:39):
Move in with him.
Speaker 2 (07:40):
Yeah, that was a while ago.
Speaker 1 (07:41):
She said no because she wanted to have proof of
a long term commitment before anything else could happen, whether
that was a proposal or a ring or something. And
in that conversation she said the words I'll even sign
a prenup yeah.
Speaker 3 (07:55):
Yeah.
Speaker 1 (07:56):
Now, there was some people in the room who thought, oh, well,
maybe she was just joking when she said that.
Speaker 4 (08:02):
But if I'm.
Speaker 1 (08:02):
Drew and I'm asking my girlfriend to move in with me,
that's not really like a joking environment. Like to me,
that's a serious thing. What do you think, Drew from
her tone in the moment, did you feel like she
was serious?
Speaker 7 (08:16):
I got the vibe that she was serious for sure.
Speaker 8 (08:19):
I hope so, because he went to a lawyer and
actually had one drawn up.
Speaker 1 (08:23):
Lawyers, So Drew needs our helped to bring it up
to her because, like Brook said, it's been a while
since that conversation happened and she hasn't brought it up since.
And I know this is a pretty sensitive topic. I've
personally never been in this situation. I know Brooke has
not dealt with it in her marriage. Alexis wishes somebody
would have this conversation with her, but nowhere near the
(08:44):
assets there. It's a tricky topic and that's why I
feel like the safe thing to do is to give
it to someone who really knows about this.
Speaker 8 (08:52):
Jose what advice do you have for Drew all those
long Relationshipjesus oay one time it lasted eight months, broke,
don't all right?
Speaker 5 (09:02):
Okay, this entire conversation can't just be about the prenum
or it's gonna sound like a downer, right, you need
to hide it in between the wedding and ring shopping
and then the prenum.
Speaker 2 (09:15):
Seriously, what a man thinks when they have important news?
Speaker 1 (09:17):
What do you distract her with shiny promises that will
only work on Jose?
Speaker 7 (09:24):
Okay, in theory, sure it sounds kind of sneaky, I
don't know, man like, but legally you.
Speaker 3 (09:31):
Still mention it.
Speaker 1 (09:32):
It's a terrible idea like that a little bit about
the engagement in the future.
Speaker 4 (09:38):
But Brook, what do you think?
Speaker 8 (09:39):
I think you you make sure that you frame it
as you are doing something for her. You say, listen,
you said that you wanted this done.
Speaker 7 (09:48):
I did it.
Speaker 8 (09:49):
Some people, you know, all talk, But I'm a doer
and that's how I'm going to be in this relationship.
If you want something done, I'm the guy to get
it done.
Speaker 4 (09:57):
Look at I'm doing stuff for you. What have you
ever done for me? Maybe you should sign this?
Speaker 1 (10:02):
Yeah, I'm.
Speaker 2 (10:04):
That's a good idea to frame it that it's her idea.
Speaker 4 (10:07):
Yeah, guilt into signing it.
Speaker 7 (10:08):
All right, what do you think, Dre, No, that actually
makes a lot more sense because ultimately it was her
idea and I went forward with it thinking she was
serious about it, because why wouldn't she be.
Speaker 2 (10:19):
Now, she may be angry that you didn't include her
in the actual writing it up and stuff, but what
that's boring.
Speaker 1 (10:26):
Okay, if she gets mad about you bringing up tell
her to be mad at herself for bringing it up
in the first place.
Speaker 2 (10:33):
That's not going to end well for him.
Speaker 4 (10:35):
But sure that was Brooks advice. So here we go.
Speaker 1 (10:37):
We're gonna call Kelsey your girlfriend for you and see
if she's ready to sign a prenup and then hopefully
move in together.
Speaker 3 (10:43):
Oh I hope I don't cry during this one.
Speaker 2 (10:45):
I'm so romantic.
Speaker 7 (10:47):
I'm so nervous.
Speaker 1 (10:48):
We wish you a lot of luck, Drew. Don't be nervous.
We're all here to support you. Okay, yes, thanks, all right,
here we go, Dolly your number right now?
Speaker 6 (11:03):
Hello?
Speaker 7 (11:05):
Hey, cal, Hey, what's that babe? How's your day? You work? Yeah?
Speaker 6 (11:12):
Yeah, it was fine. It was just some normal you know,
the usual.
Speaker 7 (11:16):
Yeah, usual stuff. Do you have a minute at your
get time? Are you busy or yeah, I can keep
a second.
Speaker 6 (11:23):
What's up?
Speaker 7 (11:24):
I wanted to ask you something. Remember that day we
had that conversation we talked about moving in. Do you
remember that vaguely? Yeah?
Speaker 6 (11:37):
I think I said no, right, yeah, and which.
Speaker 7 (11:41):
Is fine, you know he said no. But it got
us talking, right, I got us talking about the future,
and it was kind of super romantic and we started
going ring shopping together. So it was it was like
a fun little day. It was cute.
Speaker 6 (11:56):
Yeah, I mean it was like more than cute. I
think it was kind of important, like put us on
a new path together.
Speaker 7 (12:03):
Mm hmm, yeah, I agree.
Speaker 6 (12:08):
Why are you being so weird? What do you mean
you agree?
Speaker 7 (12:11):
No? I mean I just I just wanted to bring
up what you had mentioned when I asked you to move.
Speaker 8 (12:18):
In with me.
Speaker 7 (12:19):
If you remember, do you remember anything about the agreement?
Speaker 6 (12:24):
You might have said or just said, I don't want
to move in with you until we get married, like.
Speaker 7 (12:31):
I told you that. Yeah, you said another word?
Speaker 6 (12:35):
Also, what's going on?
Speaker 7 (12:41):
Can you just say you know what? You know the
word I'm talking about? Can you just say it just
helps me? And you know my anxiety and.
Speaker 6 (12:47):
I don't right now?
Speaker 7 (12:49):
So I'm gonna need you to say it. It's it
starts with the P. You know what I mean?
Speaker 6 (12:58):
What's it ends with.
Speaker 5 (13:01):
Up?
Speaker 6 (13:03):
Karna? Okay?
Speaker 7 (13:04):
Yes, okay, so you did say that? Great? Okay?
Speaker 6 (13:10):
Is there other No?
Speaker 7 (13:12):
No, no, no, no, it's you. I'm just like outside,
there's like a lot of people outside running around whatever.
So I went ahead, I moved forward with that word
that that pre word. I had some lawyers involved.
Speaker 6 (13:28):
And just say lawyers. You hired a lawyer?
Speaker 7 (13:31):
Yeah, you know it's it's not legal, bigle stuff, you
know what I mean? Like you kind of have to
when you do this.
Speaker 6 (13:37):
I don't know what you're talking about right now? Can
you get to the freaking point?
Speaker 7 (13:40):
So I don't want you to get upset? This is ridiculous.
So I wanted to prove my commitment to you, like
we talked about, and I went ahead and got the
paperwork for you to sign it.
Speaker 6 (13:57):
What do you mean you want me to sign it?
This is your idea?
Speaker 7 (14:01):
Remember, this is fun.
Speaker 6 (14:05):
This is just like a weird phone call. I feel
like you could have talked to me in person about this.
Speaker 7 (14:11):
I didn't know how to bring it up. You have
no idea. I've been losing sleep about this whole damn thing,
and I asked this radio station to help me.
Speaker 6 (14:20):
The radio station, what.
Speaker 2 (14:24):
A team of radio people.
Speaker 3 (14:26):
I always want to hang up at that point.
Speaker 2 (14:29):
I don't want to be here.
Speaker 1 (14:31):
I feel like it probably went just about as well
as their first conversation about.
Speaker 6 (14:35):
I don't understand what's happening right now.
Speaker 3 (14:37):
We're a team of lawyers.
Speaker 2 (14:40):
That makes it sound like a joke.
Speaker 6 (14:41):
We don't want to do that.
Speaker 1 (14:42):
We're a radio show. This segment is called an Awkward
Tuesday phone call, oh.
Speaker 2 (14:47):
Man, and we really emphasized that title today.
Speaker 1 (14:50):
We were trying to help our listener here, Drew have
what he knew was going to be a little bit
of an awkward conversation with you.
Speaker 4 (14:58):
Uh huh.
Speaker 8 (14:59):
Apparently he he thought that you wanted a prenup, you know,
because like he wants to move in with you and
move forward and go down the marriage road.
Speaker 6 (15:07):
Well, yeah, I said that, but he never like talked
to me about pursuing it and hiring lawyers and filling
out paperwork.
Speaker 4 (15:13):
Yeah, he should have written it all up himself. I
do agree with that.
Speaker 8 (15:18):
But no, Jeffrey, oh my god, I mean I can't
tell what your emotion is right now, maybe it's just shocked.
Speaker 3 (15:28):
Didn't you want this?
Speaker 2 (15:29):
Maybe you don't care, maybe you're mad. Where are you at?
Speaker 6 (15:32):
I'm just like in the middle, really because I just
wish he was more honest and I feel like we
could have worked on it together.
Speaker 2 (15:38):
Okay, yeah, all right, so that's not bad.
Speaker 7 (15:41):
I mean, that's if I'm being honest. This wasn't one
hundred percent my idea to do it this way. The
radio is your idea, you people, you people talking microphone whatever,
you radio people, It was your idea to do this way.
Speaker 2 (15:53):
What it wasn't our idea for you to hire a
team of lawyers.
Speaker 4 (15:57):
You called us way after that, you emailed us.
Speaker 7 (16:00):
I just wanted to do a love shout out to
show I care about my my girl.
Speaker 6 (16:06):
Right, you know what?
Speaker 4 (16:07):
Oops? Did I screw that one up again?
Speaker 2 (16:11):
The world's longest shutout.
Speaker 1 (16:13):
Yes, it's three hundred and eighty seven mistakes since yesterday.
Speaker 4 (16:17):
I'm never going to get this job right.
Speaker 1 (16:19):
I'm sorry, Drew, my bad for misunderstanding your awkward Tuesday
phone request shout out.
Speaker 4 (16:25):
Yes, excuse me again? Three hundred.
Speaker 2 (16:29):
Wait, does that mean you're still wanting her to sign
the prenup, Drew.
Speaker 7 (16:33):
I don't want you guys to pressure her to go
ahead and want to sign it, that's for sure.
Speaker 3 (16:38):
Yeah, sorry about that.
Speaker 2 (16:39):
Yes, that's I was actually on the other band sign it.
But yeah, I know so much about prenup. Sorry. Would
we hire a twenty four? I love she brought it up.
Speaker 1 (16:55):
Yeah, we thought we would roll with it, all right,
that's our bad as long as you two are.
Speaker 4 (17:00):
Good, right, Yeah.
Speaker 6 (17:02):
I think we'll figure it out.
Speaker 3 (17:03):
Maybe have a couple more talks about this.
Speaker 7 (17:05):
Yeah, we'll go on a camping trip and ride in
the jeep top down or something. They'll thin out.
Speaker 3 (17:10):
Everything's better top down in a jeep.
Speaker 2 (17:14):
Seems way more chill than you, Drew.
Speaker 3 (17:15):
I think she's confused.
Speaker 7 (17:18):
Love Kelsey too.
Speaker 3 (17:22):
It's something we can shout.
Speaker 4 (17:23):
Out mission successful, Awkward
Speaker 8 (17:26):
Tuesday, Freaking Jeffrey in the morning,
What's the toughest conversation that you could ever have with
your significant other?
Speaker 2 (00:07):
Break up?
Speaker 3 (00:08):
Good thing? I don't have one, Jeff.
Speaker 1 (00:09):
Well, I mean the first one would probably be it's
not yours, the second one is it mine?
Speaker 3 (00:22):
It's yours, and it has to be.
Speaker 2 (00:23):
Well, if you're a guy, maybe you wouldn't know. But
it's a weird question to ask.
Speaker 1 (00:31):
But maybe more important than any of those, is are
you going to finish that.
Speaker 3 (00:38):
Question?
Speaker 2 (00:40):
Wow, that was an extra gas.
Speaker 3 (00:44):
Oxygen mask.
Speaker 4 (00:44):
Well, you can believe it.
Speaker 1 (00:46):
One of our listeners has a looming conversation even more
cringe than all of those combined. It's about to happen
with his longtime girlfriend. You're going to hear what it
is and see if we can help him out in
your awkward to day phone call.
Speaker 4 (01:01):
Next, It's awkward.
Speaker 2 (01:04):
It's Tuesday.
Speaker 5 (01:05):
It's awkward Tuesday phone call.
Speaker 1 (01:08):
On this segment, we've helped listeners tackle all sorts of
big pivotal moments in their love lives. We've helped people
ask somebody out, We've helped somebody propose before even help
someone on where to install the swing?
Speaker 4 (01:24):
What room is it going to fit best in?
Speaker 2 (01:27):
I don't remember that segment.
Speaker 6 (01:28):
I do.
Speaker 1 (01:29):
I'm just saying we've been there for all of our
listeners through all of their struggles, but today, I don't
think we've ever dealt with this particular issue in a
relationship before. It might be one of the biggest conversations
a couple could have. But good news is I've got
two of the best aes around.
Speaker 2 (01:48):
Advice experts always be selling.
Speaker 1 (01:55):
They're waiting to hear from Drew. So, Drew, welcome to
the show. How can we help you not screw up
your relationship?
Speaker 7 (02:02):
What's up? Guys? So? Yeah, I definitely need some help here, Okay.
Speaker 2 (02:06):
Can we start with who the relationship is with?
Speaker 7 (02:09):
Sure? So her name is Kelsey?
Speaker 2 (02:10):
Okay, okay?
Speaker 4 (02:11):
And do you already have a swing installed? Is that
what this is?
Speaker 7 (02:15):
We're not there yet, but we're talking about it.
Speaker 4 (02:18):
Call back when you need help with that. But what
are you dealing with now?
Speaker 7 (02:21):
So? I've been dating Kelsey now for the last couple
of years, so it's kind of serious.
Speaker 2 (02:25):
Yeah you guys, do you guys live together?
Speaker 7 (02:28):
No? No, not yet?
Speaker 1 (02:29):
Okay, Okay, tell us a little bit more about Kelsey.
Speaker 4 (02:32):
Who is she?
Speaker 7 (02:33):
So? She's this great, amazing woman, so much in common
she loves camping, She drives a jeep. She's like just
super old fashioned. She doesn't have social media, which I
love it. I think it's refreshing, it's new, it's great.
Speaker 4 (02:48):
Good. She's a different type of gal totally.
Speaker 7 (02:50):
I met her because I'm in real estate. So I
was showing houses one day and she came in looking
for property with some friends.
Speaker 8 (02:56):
And Okay, so she's got money too, right, I mean
she's successful.
Speaker 7 (03:00):
She's looking at her Yeah. Yeah, So we have this
great relationship.
Speaker 4 (03:05):
Okay, what's the problem.
Speaker 1 (03:07):
Why why did you email us for help with this great, amazing,
perfect relationship with this jeep driving woman.
Speaker 7 (03:13):
Well, so it's why I need you guys help because
it's really like kind of a sensitive thing. So I
was at the point after the one year mark where
I wanted her to move in with me.
Speaker 4 (03:21):
Okay, that's big.
Speaker 7 (03:24):
I asked her and straight up said, would you move
in with me? She goes, no, Okay, oh I was expecting.
Speaker 2 (03:31):
Yeah, you were not expecting that.
Speaker 7 (03:33):
No.
Speaker 1 (03:35):
Why would he ask that if he thought that she
might say no by this point.
Speaker 4 (03:39):
They would have the conversation.
Speaker 8 (03:41):
It sounds like you didn't have a Yeah, he didn't
have a conversation prior to asking, and that was the
issue that trying to.
Speaker 4 (03:47):
Start or maybe the place that you live kind of sucks.
Speaker 7 (03:50):
Well, she's explained. She gave me the reason she doesn't
want to live with a guy before she's married.
Speaker 4 (03:55):
Oh you know, I you can see that.
Speaker 8 (04:00):
Oh yeah, I didn't live with anybody until I met
my husband because it's so complicated.
Speaker 2 (04:04):
You know, then you're like combining.
Speaker 4 (04:06):
What are you talking about? You with your husband before
you were married to you know, when.
Speaker 2 (04:09):
I married him, he's the only guy I ever list.
Speaker 4 (04:11):
This is what she's saying. She doesn't want to live
with anyone until she is married.
Speaker 7 (04:15):
I mean, she doesn't necessarily want it to be after.
She just wants like a solid commitment that makes sense.
Speaker 8 (04:21):
Yea, Like by the time I moved in with my husband,
I knew this was the person I was going to
be with for the rest of my life.
Speaker 2 (04:27):
Oh like I just knew that.
Speaker 1 (04:29):
So she wants something that says that marriage is going
to be in the books. Like I'm assuming that's where
the conversation led to.
Speaker 7 (04:37):
Basically, Yeah, I mean we talked about it. We didn't
dive too deep into it. Again, like out of the blue,
he goes, I'll even sign a prenup, which I was
not even expecting.
Speaker 1 (04:47):
Whoa, whoa, that's like even more serious than marriage.
Speaker 2 (04:51):
Can you do that before you're married? I have no idea.
I don't have a breed up. I have no idea.
I mean I could see where you.
Speaker 8 (04:57):
Would want some sort of like is it because she's
worried about combining your stuff or saying I have.
Speaker 3 (05:03):
Money like we were talking about and she doesn't want
you to take it.
Speaker 7 (05:06):
Well, I kind of have the money. I mean, I
own a bunch of property and she knows that. So
that's why she said that.
Speaker 3 (05:15):
So she's saying it's not about the money. She loves
you for you.
Speaker 7 (05:18):
Yeah, And the problem is now it never feels like
the right time to tell her that I've already met
with the lawyer and I've already had these papers already
drawn up and all that, because I've done that and
I'm ready for.
Speaker 5 (05:30):
This next set with lawyers, and he's he's drawn up
the prenup to secure his assets before he asks her
hand in marriage.
Speaker 4 (05:38):
That's so romantic.
Speaker 3 (05:39):
It is so you have to get down one knee
and say, will you take this pen and document?
Speaker 2 (05:49):
Right, I'm your idea.
Speaker 8 (05:50):
Well, she mentioned, but it sounds like you guys didn't
have a lot of conversations.
Speaker 2 (05:54):
So where are you at right now with everything?
Speaker 5 (05:55):
Yeah?
Speaker 3 (05:56):
Good question.
Speaker 7 (05:57):
So I want to mention it before I pose, not after.
You know what I mean, and I need help bringing
it up. You know it's not.
Speaker 1 (06:04):
Weird, Okay, So you want our help to let her
know that there is a prenup ready for her to
sign whenever she wants, and then after that then we'll
start the engagements and serious commitments that she's always wanted.
Speaker 7 (06:18):
Yeah, okay, why didn't you?
Speaker 1 (06:20):
Okay, So I mean if if she was the one
who brought it up and it's her idea, then what
are you worried about?
Speaker 2 (06:26):
Why didn't you just tell her? I don't understand that,
Like I.
Speaker 7 (06:29):
Don't because it's not a it's a very sensitive topic
when it comes to money and assets. I feel a
little strange about having that discussion, to be honest, Well.
Speaker 5 (06:37):
And even could have been not joking, but she could
have just been throwing it out there and not been
like actually serious and like wait, you actually drew up
the documents.
Speaker 3 (06:46):
That's another level.
Speaker 2 (06:47):
Just feel like it'd be a red flag to me,
but I don't know.
Speaker 1 (06:50):
I think it's a very romantic move. I don't know why,
just trying to kill the NaNs in this segment, was you.
Speaker 3 (06:57):
Lawyered up before you?
Speaker 2 (06:58):
I'm pretty anti preno?
Speaker 4 (07:00):
Yeah, well know what, We're going to go to work
here for you, Okay, Drew.
Speaker 1 (07:03):
We're going to find out the most romantic, over the
top way to tell somebody. I have a prenup ready
for you to sign.
Speaker 7 (07:13):
I appreciate that I need help with your so much.
Speaker 2 (07:14):
You could like dot your eyes with a heart.
Speaker 4 (07:18):
The ideas are already flowing.
Speaker 1 (07:20):
We're gonna start your happily ever after when we do
your awkward Tuesday phone call right after this.
Speaker 4 (07:27):
It's awkward.
Speaker 2 (07:28):
It's Tuesday.
Speaker 4 (07:30):
It's awkward Tuesday phone call.
Speaker 1 (07:32):
I think we need to clarify something here before we
move on. Because the listener on the phone, Drew asked
his girlfriend to.
Speaker 4 (07:39):
Move in with him.
Speaker 2 (07:40):
Yeah, that was a while ago.
Speaker 1 (07:41):
She said no because she wanted to have proof of
a long term commitment before anything else could happen, whether
that was a proposal or a ring or something. And
in that conversation she said the words I'll even sign
a prenup yeah.
Speaker 3 (07:55):
Yeah.
Speaker 1 (07:56):
Now, there was some people in the room who thought, oh, well,
maybe she was just joking when she said that.
Speaker 4 (08:02):
But if I'm.
Speaker 1 (08:02):
Drew and I'm asking my girlfriend to move in with me,
that's not really like a joking environment. Like to me,
that's a serious thing. What do you think, Drew from
her tone in the moment, did you feel like she
was serious?
Speaker 7 (08:16):
I got the vibe that she was serious for sure.
Speaker 8 (08:19):
I hope so, because he went to a lawyer and
actually had one drawn up.
Speaker 1 (08:23):
Lawyers, So Drew needs our helped to bring it up
to her because, like Brook said, it's been a while
since that conversation happened and she hasn't brought it up since.
And I know this is a pretty sensitive topic. I've
personally never been in this situation. I know Brooke has
not dealt with it in her marriage. Alexis wishes somebody
would have this conversation with her, but nowhere near the
(08:44):
assets there. It's a tricky topic and that's why I
feel like the safe thing to do is to give
it to someone who really knows about this.
Speaker 8 (08:52):
Jose what advice do you have for Drew all those
long Relationshipjesus oay one time it lasted eight months, broke,
don't all right?
Speaker 5 (09:02):
Okay, this entire conversation can't just be about the prenum
or it's gonna sound like a downer, right, you need
to hide it in between the wedding and ring shopping
and then the prenum.
Speaker 2 (09:15):
Seriously, what a man thinks when they have important news?
Speaker 1 (09:17):
What do you distract her with shiny promises that will
only work on Jose?
Speaker 7 (09:24):
Okay, in theory, sure it sounds kind of sneaky, I
don't know, man like, but legally you.
Speaker 3 (09:31):
Still mention it.
Speaker 1 (09:32):
It's a terrible idea like that a little bit about
the engagement in the future.
Speaker 4 (09:38):
But Brook, what do you think?
Speaker 8 (09:39):
I think you you make sure that you frame it
as you are doing something for her. You say, listen,
you said that you wanted this done.
Speaker 7 (09:48):
I did it.
Speaker 8 (09:49):
Some people, you know, all talk, But I'm a doer
and that's how I'm going to be in this relationship.
If you want something done, I'm the guy to get
it done.
Speaker 4 (09:57):
Look at I'm doing stuff for you. What have you
ever done for me? Maybe you should sign this?
Speaker 1 (10:02):
Yeah, I'm.
Speaker 2 (10:04):
That's a good idea to frame it that it's her idea.
Speaker 4 (10:07):
Yeah, guilt into signing it.
Speaker 7 (10:08):
All right, what do you think, Dre, No, that actually
makes a lot more sense because ultimately it was her
idea and I went forward with it thinking she was
serious about it, because why wouldn't she be.
Speaker 2 (10:19):
Now, she may be angry that you didn't include her
in the actual writing it up and stuff, but what
that's boring.
Speaker 1 (10:26):
Okay, if she gets mad about you bringing up tell
her to be mad at herself for bringing it up
in the first place.
Speaker 2 (10:33):
That's not going to end well for him.
Speaker 4 (10:35):
But sure that was Brooks advice. So here we go.
Speaker 1 (10:37):
We're gonna call Kelsey your girlfriend for you and see
if she's ready to sign a prenup and then hopefully
move in together.
Speaker 3 (10:43):
Oh I hope I don't cry during this one.
Speaker 2 (10:45):
I'm so romantic.
Speaker 7 (10:47):
I'm so nervous.
Speaker 1 (10:48):
We wish you a lot of luck, Drew. Don't be nervous.
We're all here to support you. Okay, yes, thanks, all right,
here we go, Dolly your number right now?
Speaker 6 (11:03):
Hello?
Speaker 7 (11:05):
Hey, cal, Hey, what's that babe? How's your day? You work? Yeah?
Speaker 6 (11:12):
Yeah, it was fine. It was just some normal you know,
the usual.
Speaker 7 (11:16):
Yeah, usual stuff. Do you have a minute at your
get time? Are you busy or yeah, I can keep
a second.
Speaker 6 (11:23):
What's up?
Speaker 7 (11:24):
I wanted to ask you something. Remember that day we
had that conversation we talked about moving in. Do you
remember that vaguely? Yeah?
Speaker 6 (11:37):
I think I said no, right, yeah, and which.
Speaker 7 (11:41):
Is fine, you know he said no. But it got
us talking, right, I got us talking about the future,
and it was kind of super romantic and we started
going ring shopping together. So it was it was like
a fun little day. It was cute.
Speaker 6 (11:56):
Yeah, I mean it was like more than cute. I
think it was kind of important, like put us on
a new path together.
Speaker 7 (12:03):
Mm hmm, yeah, I agree.
Speaker 6 (12:08):
Why are you being so weird? What do you mean
you agree?
Speaker 7 (12:11):
No? I mean I just I just wanted to bring
up what you had mentioned when I asked you to move.
Speaker 8 (12:18):
In with me.
Speaker 7 (12:19):
If you remember, do you remember anything about the agreement?
Speaker 6 (12:24):
You might have said or just said, I don't want
to move in with you until we get married, like.
Speaker 7 (12:31):
I told you that. Yeah, you said another word?
Speaker 6 (12:35):
Also, what's going on?
Speaker 7 (12:41):
Can you just say you know what? You know the
word I'm talking about? Can you just say it just
helps me? And you know my anxiety and.
Speaker 6 (12:47):
I don't right now?
Speaker 7 (12:49):
So I'm gonna need you to say it. It's it
starts with the P. You know what I mean?
Speaker 6 (12:58):
What's it ends with.
Speaker 5 (13:01):
Up?
Speaker 6 (13:03):
Karna? Okay?
Speaker 7 (13:04):
Yes, okay, so you did say that? Great? Okay?
Speaker 6 (13:10):
Is there other No?
Speaker 7 (13:12):
No, no, no, no, it's you. I'm just like outside,
there's like a lot of people outside running around whatever.
So I went ahead, I moved forward with that word
that that pre word. I had some lawyers involved.
Speaker 6 (13:28):
And just say lawyers. You hired a lawyer?
Speaker 7 (13:31):
Yeah, you know it's it's not legal, bigle stuff, you
know what I mean? Like you kind of have to
when you do this.
Speaker 6 (13:37):
I don't know what you're talking about right now? Can
you get to the freaking point?
Speaker 7 (13:40):
So I don't want you to get upset? This is ridiculous.
So I wanted to prove my commitment to you, like
we talked about, and I went ahead and got the
paperwork for you to sign it.
Speaker 6 (13:57):
What do you mean you want me to sign it?
This is your idea?
Speaker 7 (14:01):
Remember, this is fun.
Speaker 6 (14:05):
This is just like a weird phone call. I feel
like you could have talked to me in person about this.
Speaker 7 (14:11):
I didn't know how to bring it up. You have
no idea. I've been losing sleep about this whole damn thing,
and I asked this radio station to help me.
Speaker 6 (14:20):
The radio station, what.
Speaker 2 (14:24):
A team of radio people.
Speaker 3 (14:26):
I always want to hang up at that point.
Speaker 2 (14:29):
I don't want to be here.
Speaker 1 (14:31):
I feel like it probably went just about as well
as their first conversation about.
Speaker 6 (14:35):
I don't understand what's happening right now.
Speaker 3 (14:37):
We're a team of lawyers.
Speaker 2 (14:40):
That makes it sound like a joke.
Speaker 6 (14:41):
We don't want to do that.
Speaker 1 (14:42):
We're a radio show. This segment is called an Awkward
Tuesday phone call, oh.
Speaker 2 (14:47):
Man, and we really emphasized that title today.
Speaker 1 (14:50):
We were trying to help our listener here, Drew have
what he knew was going to be a little bit
of an awkward conversation with you.
Speaker 4 (14:58):
Uh huh.
Speaker 8 (14:59):
Apparently he he thought that you wanted a prenup, you know,
because like he wants to move in with you and
move forward and go down the marriage road.
Speaker 6 (15:07):
Well, yeah, I said that, but he never like talked
to me about pursuing it and hiring lawyers and filling
out paperwork.
Speaker 4 (15:13):
Yeah, he should have written it all up himself. I
do agree with that.
Speaker 8 (15:18):
But no, Jeffrey, oh my god, I mean I can't
tell what your emotion is right now, maybe it's just shocked.
Speaker 3 (15:28):
Didn't you want this?
Speaker 2 (15:29):
Maybe you don't care, maybe you're mad. Where are you at?
Speaker 6 (15:32):
I'm just like in the middle, really because I just
wish he was more honest and I feel like we
could have worked on it together.
Speaker 2 (15:38):
Okay, yeah, all right, so that's not bad.
Speaker 7 (15:41):
I mean, that's if I'm being honest. This wasn't one
hundred percent my idea to do it this way. The
radio is your idea, you people, you people talking microphone whatever,
you radio people, It was your idea to do this way.
Speaker 2 (15:53):
What it wasn't our idea for you to hire a
team of lawyers.
Speaker 4 (15:57):
You called us way after that, you emailed us.
Speaker 7 (16:00):
I just wanted to do a love shout out to
show I care about my my girl.
Speaker 6 (16:06):
Right, you know what?
Speaker 4 (16:07):
Oops? Did I screw that one up again?
Speaker 2 (16:11):
The world's longest shutout.
Speaker 1 (16:13):
Yes, it's three hundred and eighty seven mistakes since yesterday.
Speaker 4 (16:17):
I'm never going to get this job right.
Speaker 1 (16:19):
I'm sorry, Drew, my bad for misunderstanding your awkward Tuesday
phone request shout out.
Speaker 4 (16:25):
Yes, excuse me again? Three hundred.
Speaker 2 (16:29):
Wait, does that mean you're still wanting her to sign
the prenup, Drew.
Speaker 7 (16:33):
I don't want you guys to pressure her to go
ahead and want to sign it, that's for sure.
Speaker 3 (16:38):
Yeah, sorry about that.
Speaker 2 (16:39):
Yes, that's I was actually on the other band sign it.
But yeah, I know so much about prenup. Sorry. Would
we hire a twenty four? I love she brought it up.
Speaker 1 (16:55):
Yeah, we thought we would roll with it, all right,
that's our bad as long as you two are.
Speaker 4 (17:00):
Good, right, Yeah.
Speaker 6 (17:02):
I think we'll figure it out.
Speaker 3 (17:03):
Maybe have a couple more talks about this.
Speaker 7 (17:05):
Yeah, we'll go on a camping trip and ride in
the jeep top down or something. They'll thin out.
Speaker 3 (17:10):
Everything's better top down in a jeep.
Speaker 2 (17:14):
Seems way more chill than you, Drew.
Speaker 3 (17:15):
I think she's confused.
Speaker 7 (17:18):
Love Kelsey too.
Speaker 3 (17:22):
It's something we can shout.
Speaker 4 (17:23):
Out mission successful, Awkward
Speaker 8 (17:26):
Tuesday, Freaking Jeffrey in the morning,
Hosts And Creators
Brooke Fox
Jeffrey "Young Jeffrey" Dubow
Alexis Fuller
Jose Bolanos
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