June 24, 2025 • 20 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 (00:00):
It's your second Ay podcast and today with Brook and
Jeffrey in the morning, we have an awkward Tuesday phone
call because.
Speaker 2 (00:04):
It's it's Tuesday.
Speaker 1 (00:06):
But I was just looking through the stats on our
podcast and I always think it's fascinating to see where
people are listening from. And I always look at like
the top five countries. It's like the US, Canada, the UK, Australia,
the Philippines, which is amazing. But I scrolled all the
way down to see where we get the least amount
of listeners.
Speaker 2 (00:24):
There's like one person. Yeah, I love doing that.
Speaker 1 (00:26):
We've got one listener in Sri Lanka, if that's you,
please leave a comment, yes, and one in Equatorial Guinea.
Speaker 2 (00:34):
All right, I know we need to look it up.
Comment please. Yeah. So anyway, that's your update. But we
do love to look at the comments and learn more
about you all. So what do you got, Alexis.
Speaker 3 (00:45):
I saw one from Uie who said, I'm not sure
whether I should thank you guys or stop listening to
the show. The level of cringiness I can tolerate has
increased tremendously. At the beginning, I would pause a segment
just to breathe and get myself together. But now I
can in two to three segments in a row, no
matter how cringey the conversation is. That's right, Thanks, I
guess love from Miami.
Speaker 2 (01:06):
We're breaking you.
Speaker 4 (01:06):
Down, We're moving your bar lower and lower.
Speaker 2 (01:09):
Yeah, exactly, that's exactly right.
Speaker 1 (01:11):
I'm going to keep doing it too, because right now
it's your awkward Tuesday phone call.
Speaker 5 (01:16):
What's the toughest conversation that you could ever have with
your significant other?
Speaker 2 (01:23):
Break up?
Speaker 5 (01:24):
Good thing I don't have one, Jeff. Well, I mean,
the first one would probably be it's not yours?
Speaker 2 (01:31):
WHOA?
Speaker 5 (01:33):
The second one is it mine?
Speaker 2 (01:37):
It's not yours? And it has to be Well.
Speaker 1 (01:39):
I mean, if you're a guy, maybe you wouldn't know,
But if you're a woman, it's a weird question to ask.
Speaker 5 (01:47):
Yeah, but maybe more important than any of those, is
are you going to finish that question?
Speaker 6 (01:55):
Wow?
Speaker 2 (01:56):
That was an extra guest. Can we get some oxygen?
Speaker 5 (02:00):
Well, you can believe it. 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 gonna
hear what it is and see if we can help
him out in your awkward Tuesday phone call.
Speaker 7 (02:16):
Next, It's awkward, It's Tuesday. It's awkward Tuesday phone call.
Speaker 5 (02:24):
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? What room is
it going to fit best in?
Speaker 2 (02:42):
I don't remember that segment.
Speaker 8 (02:44):
I do.
Speaker 5 (02:45):
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, account a vice experts.
Speaker 2 (03:06):
Oh selling.
Speaker 5 (03:10):
I wonder they're waiting to hear from Drew. So, Drew,
welcome to the show. How can we help you not
screw up your relationship?
Speaker 6 (03:18):
What's up? Guys?
Speaker 5 (03:19):
So?
Speaker 6 (03:19):
Yeah, definitely need some help here.
Speaker 2 (03:21):
Okay? Can we start with who the relationship is with?
Speaker 6 (03:24):
Sure?
Speaker 8 (03:25):
So?
Speaker 6 (03:25):
Her name is Kelsey?
Speaker 5 (03:26):
Okay, okay, and do you already have a swing? Installed
is that what this is?
Speaker 6 (03:30):
We're not there yet, but we're talking about it.
Speaker 5 (03:33):
Call back when you need help with that. But what
are you dealing with now?
Speaker 6 (03:37):
So I've been dating Kelsey now for the last couple
of years, so it's kind of serious.
Speaker 1 (03:41):
Yeah you guys, do you guys live together?
Speaker 6 (03:44):
No? No, not yet.
Speaker 5 (03:45):
Okay, tell us a little bit more about Kelsey. Who
is she?
Speaker 6 (03:49):
So she's this great, amazing woman, so much in common.
She loves camping, she drives a jeep. She's like this
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 5 (04:03):
Good. She's a different type of gal totally.
Speaker 6 (04:06):
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 1 (04:12):
And Okay, so she's got money too, right, that means
she's successful.
Speaker 6 (04:16):
She's looking at her Yeah, yeah, yeah, So we have
this great relationship.
Speaker 5 (04:21):
Okay, what's the problem. Why why did you email us
for help with this great, amazing, perfect relationship with this
jeep driving woman.
Speaker 6 (04:28):
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 5 (04:37):
Okay, that's big.
Speaker 6 (04:39):
I asked her and straight up said, would you move
in with me? She goes no, okay, which, oh I
was expecting.
Speaker 2 (04:46):
Yeah, you were not expecting that.
Speaker 5 (04:49):
No, why would he ask that if he thought that
she might say no by this point, the would the conversation.
Speaker 1 (04:57):
It sounds like you didn't have a Yeah, he did
have a conversation prior to asking, and that was the
issue trying.
Speaker 5 (05:03):
To start or maybe the place that you live kind
of sucks.
Speaker 6 (05:06):
Well, she's explained. She gave me the reason she doesn't
want to live with a guy before she's married.
Speaker 5 (05:10):
Oh, you know, I can see that.
Speaker 1 (05:15):
Oh yeah, I didn't live with anybody until I met
my husband because it's so complicated.
Speaker 2 (05:20):
You know, then you're like combining.
Speaker 5 (05:21):
What are you talking about? You with your husband before
you were married to.
Speaker 2 (05:25):
You know, when I married him, he's the only guy
I ever list.
Speaker 5 (05:27):
This is what she's saying. She doesn't want to live
with anyone until she is.
Speaker 6 (05:30):
Mari No, I mean she doesn't necessarily want it to
be after. She just wants like a solid commitment that makes.
Speaker 1 (05:36):
Sense 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 (05:43):
Oh like I just knew that.
Speaker 5 (05:45):
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 6 (05:52):
Basically, Yeah, I mean we talked about it, we didn't
dive too deep into it. But then like out of
the blue, he goes, I'll even sign the prenup, which
I was not even expecting.
Speaker 5 (06:02):
Whoa, whoa, that's like even more serious than marriage.
Speaker 2 (06:06):
Can you do that before you're married? You know, I
have no idea. I don't have a pre up. I
have no idea.
Speaker 1 (06:12):
I mean I could see where you would want some
sort of like is it because she's worried about combining
your stuff or what I'm saying.
Speaker 4 (06:19):
I have money, like we were talking about, and she
doesn't want.
Speaker 6 (06:21):
You to take it. 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 4 (06:30):
So she's saying it's not about the money.
Speaker 5 (06:32):
She loves you for you.
Speaker 6 (06:34):
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 this next step.
Speaker 1 (06:47):
He's met with lawyers and he's he's drawn up the
prenup to secure his assets before he asks her band
in marriage.
Speaker 5 (06:54):
That's so romantic, it is, so you have to get
down on one knee and say will you take this pen?
Speaker 2 (07:00):
And she wanted right, I'm your idea?
Speaker 5 (07:06):
Well she mentioned it.
Speaker 1 (07:07):
Yeah, but it sounds like you guys didn't have a
lot of conversations. So where are you at right now
with everything?
Speaker 8 (07:11):
Yeah?
Speaker 5 (07:11):
Good question.
Speaker 6 (07:12):
So I want to mention it before I propose, not after.
You know what I mean, And I need help bringing
it up.
Speaker 5 (07:19):
You know it's not 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 6 (07:34):
Yeah, why didn't you?
Speaker 8 (07:36):
Okay?
Speaker 5 (07:36):
So I mean if she was the one who brought
it up and it's her idea, then what are you
worried about it.
Speaker 2 (07:42):
Why didn't you just tell her? I don't understand that, like.
Speaker 6 (07:45):
I don't because it's not it's 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 4 (07:52):
And even could have been not joking, but she could
have just been throwing it out there and not been like,
actually serious, Wait, you actually drew up the documents.
Speaker 2 (08:01):
That's another level. Just feel like it'd be a red
flag to me. But I don't know.
Speaker 5 (08:06):
I think it's a very romantic move. I don't know
why is trying to kill the romans in this segment,
lawyered up.
Speaker 2 (08:14):
I'm pretty anti prenup.
Speaker 5 (08:16):
I know what we're going to go to work here
for you, okay, Drew. We're going to find out the
most romantic, over the top way to tell somebody I
have a prenup ready for your sign.
Speaker 6 (08:28):
I appreciate that I need help with just.
Speaker 2 (08:30):
So many you could like dot your eyes with a
heart when.
Speaker 5 (08:34):
The ideas are already flowing. We're gonna start your happily
ever after when we do your awkward Tuesday phone call
right after this.
Speaker 7 (08:42):
It's awkward, it's Tuesday. It's awkward Tuesday phone call.
Speaker 5 (08:48):
I think we need to clarify something here before we
move on, because the listener on the phone, Drew asked
his girlfriend to move in with him.
Speaker 2 (08:55):
Yeah, that was a while ago.
Speaker 5 (08:57):
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.
Speaker 2 (09:10):
Yeah.
Speaker 6 (09:11):
Yeah.
Speaker 5 (09:12):
Now, there was some people in the room who thought, oh, well,
maybe she was just joking when she said that. But
if I'm 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 6 (09:31):
I got the vibe that she was serious for sure.
Speaker 1 (09:34):
I hope so, because he went to a lawyer and
actually had one drawn up lawyers.
Speaker 2 (09:39):
Yeah.
Speaker 5 (09:40):
Now, so Drew needs our helped to bring it up
to her cause, 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
assets there. It's a tricky topic, and that's why I
(10:04):
feel like the safe thing to do is to give
it to someone who really knows about this. Jose, what
advice do you have for drew all.
Speaker 2 (10:10):
Those long relationshipesus?
Speaker 4 (10:13):
Okay, one time it lasted eight months, Broke, don't make
fun of me, all right, Okay, this entire conversation can't
just be about the prenum or it's gonna sound like
a downer, right.
Speaker 5 (10:24):
You need to.
Speaker 4 (10:25):
Hide it in between the wedding and ring shopping and
then the prenum.
Speaker 2 (10:30):
Seriously, think have important news.
Speaker 5 (10:34):
Distract her with shiny promises that will only work on Jose, Okay,
shopping and theory.
Speaker 6 (10:42):
Sure it sounds kind of sneaky, I don't know, man
like sneaky.
Speaker 4 (10:46):
But legally you still mention it.
Speaker 5 (10:48):
It's a terrible idea like that A little bit about
the engagement in the future. But Brook, what do you think?
Speaker 1 (10:54):
I think you you make sure that you frame it
as you are doing something for her.
Speaker 2 (11:00):
You say, listen, you said that you wanted this done.
I did it. Some people, you know, all talk, but.
Speaker 1 (11:07):
I'm a doer and that's how I'm gonna be in
this relationship.
Speaker 2 (11:10):
If you want something done, I'm the guy to get
it done.
Speaker 5 (11:12):
Look it, I'm doing stuff for you. What have you
ever done for me? Maybe you should sign this prema.
That's a good idea.
Speaker 2 (11:21):
Me to frame it that it's her idea.
Speaker 5 (11:23):
Yeah, guilter into signing it? All right? What do you think, Drew?
Speaker 6 (11:26):
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 you be.
Speaker 1 (11:34):
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 5 (11:41):
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 (11:49):
That's not going to end well for him.
Speaker 5 (11:50):
But sure, that was Brooks advice. So here we go.
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 8 (11:59):
I hope.
Speaker 2 (11:59):
I'm so romantic.
Speaker 6 (12:03):
I'm so nervous.
Speaker 5 (12:04):
We wish you a lot of luck. You don't be nervous.
We're all here to support you. Okay, yes, thanks, all right,
here we go down on your number right now.
Speaker 6 (12:19):
Hello, Hey, cal.
Speaker 8 (12:23):
Hey, what's that babe?
Speaker 6 (12:25):
How's your day? Your work?
Speaker 4 (12:27):
Yeah?
Speaker 8 (12:27):
Yeah, it was fine. It was just some normal you know,
the usual.
Speaker 6 (12:32):
Yeah, usual stuff. Do you have a minute? You give time?
Are you visier?
Speaker 5 (12:37):
Yeah?
Speaker 8 (12:37):
I can take a second.
Speaker 1 (12:38):
What's up?
Speaker 6 (12:40):
I wanted to ask you something. Remember that day we
had that conversation we talked about moving in. Do you
remember that vague? Yeah? I think I said no, right, yeah,
and which is fine, you know he said no. But
it got us talking, right, I got us talking about
(13:01):
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 8 (13:11):
Yeah, I mean I was like more than cute. I
think it was kind of important, like put us on
a new path together.
Speaker 6 (13:19):
Mm hmm, yeah, I agree.
Speaker 8 (13:24):
Why are you being so weird? What do you mean
you agree? No?
Speaker 6 (13:27):
I mean I just I just wanted to bring up
what you had mentioned when I asked you to move
in with me. If you remember, do you remember anything
about the agreement?
Speaker 8 (13:40):
You might have said, well, I just said I don't
want to move in with you until we get married,
like I told you that.
Speaker 6 (13:48):
Yeah, you said another word?
Speaker 8 (13:51):
Also, what's going on?
Speaker 6 (13:57):
Can you just say you know what? You know the
word I'm talking about? Can you just it just helps me?
And you know my anxiety?
Speaker 8 (14:03):
And I don't right now, So I'm gonna need.
Speaker 6 (14:05):
You to say it. It's it starts with the P,
you know what I mean?
Speaker 8 (14:13):
What's it ends with.
Speaker 6 (14:17):
Uprea?
Speaker 8 (14:19):
Okay?
Speaker 6 (14:20):
Yeah, okay, so you did say that. Great, Okay, is
there other No? 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, and.
Speaker 8 (14:44):
Just say lawyers. You hired a lawyer.
Speaker 6 (14:47):
Yeah, you know it's it's not legal beagle stuff, you
know what I mean? Like you kind of have to
when you do this.
Speaker 8 (14:53):
I don't know what you're talking about right now. Can
you get to the freaking point?
Speaker 6 (14:56):
So I don't want you to get upset. This is ridiculous.
So I 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 8 (15:12):
What do you mean you want me to sign it?
Speaker 6 (15:15):
This is your idea? Remember, this is your idea. This
is fun.
Speaker 8 (15:21):
This is just like a weird phone call. I feel
like you could have talked to me in person about this.
Speaker 6 (15:27):
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 rest.
Speaker 8 (15:35):
The radio station, what.
Speaker 2 (15:40):
Team radio people? I always wanted to hang up at
that point. I don't want to be here.
Speaker 5 (15:47):
I feel like it probably went just about as well
as their first conversation about.
Speaker 8 (15:50):
I don't understand what's happening right now, lawyers.
Speaker 2 (15:56):
That makes it sound like a joke. We don't want
to do that.
Speaker 5 (15:58):
We're reading show. This segment is called an Awkward Tuesday phone.
Speaker 1 (16:02):
Call, oh man, and we really emphasized that title today.
Speaker 5 (16:06):
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 8 (16:14):
Uh huh.
Speaker 1 (16:15):
Apparently 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 8 (16:22):
Well yeah, I said that, but he never like talk
to me about pursuing it and hiring lawyers and filling
out paperwork.
Speaker 5 (16:29):
Yeah, he should have written it all up himself. I
do agree with that, But no, Jeffery, Oh my god.
Speaker 2 (16:40):
I mean I can't tell what your emotion is right now.
Maybe it's just shocked.
Speaker 5 (16:43):
Didn't you want this?
Speaker 2 (16:44):
Maybe you don't care, maybe you're mad. Where are you at?
Speaker 8 (16:47):
I'm just like in the middle, really because I just
wish he was more honest and I feel like we
could have looked on it together.
Speaker 2 (16:54):
Okay, yeah, all right, So that's not bad.
Speaker 6 (16:57):
I mean that's I mean honest. This wasn't one hundred
sent 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 1 (17:09):
What it wasn't our idea for you to hire a
team of lawyers.
Speaker 2 (17:12):
You called us way after that, you.
Speaker 5 (17:14):
Emailed us, Drew.
Speaker 6 (17:15):
I just wanted to do a love shout out to
show I care about my my girl.
Speaker 7 (17:20):
Oh right.
Speaker 5 (17:22):
You know what, did I screw that one up again?
Speaker 2 (17:27):
The world's longest shutout.
Speaker 5 (17:29):
It's three hundred and eighty seven mistakes since yesterday. I'm
never going to get this job right. I'm sorry, Drew,
My bad for misunderstanding your awkward Tuesday phone request. Shout
out yes, excuse me again? Three?
Speaker 8 (17:45):
Wait?
Speaker 2 (17:45):
Does that mean you're still wanting her to sign the prenup? Drew?
Speaker 6 (17:48):
I don't want you guys to pressure her to go
ahead and want to sign it, that's for sure.
Speaker 4 (17:54):
Yeah, sorry about that.
Speaker 2 (17:56):
I was actually on the other band. I sign it,
but Alexis's fault. Yeah, I know so much about preanup.
Speaker 3 (18:02):
Sorry?
Speaker 2 (18:07):
Would we hire a twenty four hour I love she
brought it up.
Speaker 5 (18:11):
Yeah, we thought we would roll with it as long
as you two are good, right, Yeah.
Speaker 8 (18:18):
I think we'll figure it out.
Speaker 5 (18:19):
Maybe have a couple more talks about this.
Speaker 6 (18:21):
Yeah, we'll go on a camping trip and ride the
jeep top down or something.
Speaker 5 (18:25):
Everything's better top down in a jeep.
Speaker 2 (18:29):
Seems way more chill than you, Drew.
Speaker 5 (18:31):
I think she's confused.
Speaker 2 (18:34):
Love, that's something we can shout.
Speaker 5 (18:39):
Out successful awkward.
Speaker 6 (18:42):
Tuesday, freaking Jeffrey in the morning, I.
Speaker 1 (18:46):
Mean, then, who said romance wasn't dead? Greenups before moving in?
Speaker 2 (18:53):
That's a lot for anything.
Speaker 4 (18:54):
Yeah, I think in today's society this is good for legalities.
I'm gonna put this in my tender bio.
Speaker 5 (18:58):
If you swipe right, you agree to a prenup.
Speaker 1 (19:04):
A lot of problems and then you could put in
little tidy words all the stuff that she owes you.
Speaker 2 (19:09):
Yeah. Yeah, you're like, you didn't read the terms and conditions.
Speaker 1 (19:13):
That's on you, my man or my friend or Mike girl,
whoever you end up datingbody. And we did get a
lot of comments already from this Awkward Tuesday.
Speaker 2 (19:22):
Yeah, prenups always have mixed responses. Yeah, but I just
threw my wedding ring offs. Oh just have his own
will my bad? I'm not a prenup later Awkward Tuesday.
Speaker 3 (19:38):
Yeah, anyways, a lot of people saying prenup before proposing.
Speaker 2 (19:41):
That's crazy. In the place of it, it.
Speaker 5 (19:43):
Should be a long conversation.
Speaker 2 (19:45):
Were moving in a lot.
Speaker 3 (19:46):
Of red flags, you know, yeah, a little words.
Speaker 2 (19:49):
I'm not going to read that. There's mean words. It's
hard already.
Speaker 1 (19:53):
All right, leave your comments, thank you for being here,
and we'll be back tomorrow with another second date update
right here on. You know, we're going to call it
your favorite podcast, just because we want to lie to ourselves.
Let's call yeah, subscribe and share. It's Brook and Jeffrey
in the Morning
Speaker 2 (20:06):
Brook and Jeffrey in the Morning,
It's your second Ay podcast and today with Brook and
Jeffrey in the morning, we have an awkward Tuesday phone
call because.
Speaker 2 (00:04):
It's it's Tuesday.
Speaker 1 (00:06):
But I was just looking through the stats on our
podcast and I always think it's fascinating to see where
people are listening from. And I always look at like
the top five countries. It's like the US, Canada, the UK, Australia,
the Philippines, which is amazing. But I scrolled all the
way down to see where we get the least amount
of listeners.
Speaker 2 (00:24):
There's like one person. Yeah, I love doing that.
Speaker 1 (00:26):
We've got one listener in Sri Lanka, if that's you,
please leave a comment, yes, and one in Equatorial Guinea.
Speaker 2 (00:34):
All right, I know we need to look it up.
Comment please. Yeah. So anyway, that's your update. But we
do love to look at the comments and learn more
about you all. So what do you got, Alexis.
Speaker 3 (00:45):
I saw one from Uie who said, I'm not sure
whether I should thank you guys or stop listening to
the show. The level of cringiness I can tolerate has
increased tremendously. At the beginning, I would pause a segment
just to breathe and get myself together. But now I
can in two to three segments in a row, no
matter how cringey the conversation is. That's right, Thanks, I
guess love from Miami.
Speaker 2 (01:06):
We're breaking you.
Speaker 4 (01:06):
Down, We're moving your bar lower and lower.
Speaker 2 (01:09):
Yeah, exactly, that's exactly right.
Speaker 1 (01:11):
I'm going to keep doing it too, because right now
it's your awkward Tuesday phone call.
Speaker 5 (01:16):
What's the toughest conversation that you could ever have with
your significant other?
Speaker 2 (01:23):
Break up?
Speaker 5 (01:24):
Good thing I don't have one, Jeff. Well, I mean,
the first one would probably be it's not yours?
Speaker 2 (01:31):
WHOA?
Speaker 5 (01:33):
The second one is it mine?
Speaker 2 (01:37):
It's not yours? And it has to be Well.
Speaker 1 (01:39):
I mean, if you're a guy, maybe you wouldn't know,
But if you're a woman, it's a weird question to ask.
Speaker 5 (01:47):
Yeah, but maybe more important than any of those, is
are you going to finish that question?
Speaker 6 (01:55):
Wow?
Speaker 2 (01:56):
That was an extra guest. Can we get some oxygen?
Speaker 5 (02:00):
Well, you can believe it. 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 gonna
hear what it is and see if we can help
him out in your awkward Tuesday phone call.
Speaker 7 (02:16):
Next, It's awkward, It's Tuesday. It's awkward Tuesday phone call.
Speaker 5 (02:24):
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? What room is
it going to fit best in?
Speaker 2 (02:42):
I don't remember that segment.
Speaker 8 (02:44):
I do.
Speaker 5 (02:45):
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, account a vice experts.
Speaker 2 (03:06):
Oh selling.
Speaker 5 (03:10):
I wonder they're waiting to hear from Drew. So, Drew,
welcome to the show. How can we help you not
screw up your relationship?
Speaker 6 (03:18):
What's up? Guys?
Speaker 5 (03:19):
So?
Speaker 6 (03:19):
Yeah, definitely need some help here.
Speaker 2 (03:21):
Okay? Can we start with who the relationship is with?
Speaker 6 (03:24):
Sure?
Speaker 8 (03:25):
So?
Speaker 6 (03:25):
Her name is Kelsey?
Speaker 5 (03:26):
Okay, okay, and do you already have a swing? Installed
is that what this is?
Speaker 6 (03:30):
We're not there yet, but we're talking about it.
Speaker 5 (03:33):
Call back when you need help with that. But what
are you dealing with now?
Speaker 6 (03:37):
So I've been dating Kelsey now for the last couple
of years, so it's kind of serious.
Speaker 1 (03:41):
Yeah you guys, do you guys live together?
Speaker 6 (03:44):
No? No, not yet.
Speaker 5 (03:45):
Okay, tell us a little bit more about Kelsey. Who
is she?
Speaker 6 (03:49):
So she's this great, amazing woman, so much in common.
She loves camping, she drives a jeep. She's like this
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 5 (04:03):
Good. She's a different type of gal totally.
Speaker 6 (04:06):
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 1 (04:12):
And Okay, so she's got money too, right, that means
she's successful.
Speaker 6 (04:16):
She's looking at her Yeah, yeah, yeah, So we have
this great relationship.
Speaker 5 (04:21):
Okay, what's the problem. Why why did you email us
for help with this great, amazing, perfect relationship with this
jeep driving woman.
Speaker 6 (04:28):
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 5 (04:37):
Okay, that's big.
Speaker 6 (04:39):
I asked her and straight up said, would you move
in with me? She goes no, okay, which, oh I
was expecting.
Speaker 2 (04:46):
Yeah, you were not expecting that.
Speaker 5 (04:49):
No, why would he ask that if he thought that
she might say no by this point, the would the conversation.
Speaker 1 (04:57):
It sounds like you didn't have a Yeah, he did
have a conversation prior to asking, and that was the
issue trying.
Speaker 5 (05:03):
To start or maybe the place that you live kind
of sucks.
Speaker 6 (05:06):
Well, she's explained. She gave me the reason she doesn't
want to live with a guy before she's married.
Speaker 5 (05:10):
Oh, you know, I can see that.
Speaker 1 (05:15):
Oh yeah, I didn't live with anybody until I met
my husband because it's so complicated.
Speaker 2 (05:20):
You know, then you're like combining.
Speaker 5 (05:21):
What are you talking about? You with your husband before
you were married to.
Speaker 2 (05:25):
You know, when I married him, he's the only guy
I ever list.
Speaker 5 (05:27):
This is what she's saying. She doesn't want to live
with anyone until she is.
Speaker 6 (05:30):
Mari No, I mean she doesn't necessarily want it to
be after. She just wants like a solid commitment that makes.
Speaker 1 (05:36):
Sense 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 (05:43):
Oh like I just knew that.
Speaker 5 (05:45):
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 6 (05:52):
Basically, Yeah, I mean we talked about it, we didn't
dive too deep into it. But then like out of
the blue, he goes, I'll even sign the prenup, which
I was not even expecting.
Speaker 5 (06:02):
Whoa, whoa, that's like even more serious than marriage.
Speaker 2 (06:06):
Can you do that before you're married? You know, I
have no idea. I don't have a pre up. I
have no idea.
Speaker 1 (06:12):
I mean I could see where you would want some
sort of like is it because she's worried about combining
your stuff or what I'm saying.
Speaker 4 (06:19):
I have money, like we were talking about, and she
doesn't want.
Speaker 6 (06:21):
You to take it. 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 4 (06:30):
So she's saying it's not about the money.
Speaker 5 (06:32):
She loves you for you.
Speaker 6 (06:34):
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 this next step.
Speaker 1 (06:47):
He's met with lawyers and he's he's drawn up the
prenup to secure his assets before he asks her band
in marriage.
Speaker 5 (06:54):
That's so romantic, it is, so you have to get
down on one knee and say will you take this pen?
Speaker 2 (07:00):
And she wanted right, I'm your idea?
Speaker 5 (07:06):
Well she mentioned it.
Speaker 1 (07:07):
Yeah, but it sounds like you guys didn't have a
lot of conversations. So where are you at right now
with everything?
Speaker 8 (07:11):
Yeah?
Speaker 5 (07:11):
Good question.
Speaker 6 (07:12):
So I want to mention it before I propose, not after.
You know what I mean, And I need help bringing
it up.
Speaker 5 (07:19):
You know it's not 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 6 (07:34):
Yeah, why didn't you?
Speaker 8 (07:36):
Okay?
Speaker 5 (07:36):
So I mean if she was the one who brought
it up and it's her idea, then what are you
worried about it.
Speaker 2 (07:42):
Why didn't you just tell her? I don't understand that, like.
Speaker 6 (07:45):
I don't because it's not it's 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 4 (07:52):
And even could have been not joking, but she could
have just been throwing it out there and not been like,
actually serious, Wait, you actually drew up the documents.
Speaker 2 (08:01):
That's another level. Just feel like it'd be a red
flag to me. But I don't know.
Speaker 5 (08:06):
I think it's a very romantic move. I don't know
why is trying to kill the romans in this segment,
lawyered up.
Speaker 2 (08:14):
I'm pretty anti prenup.
Speaker 5 (08:16):
I know what we're going to go to work here
for you, okay, Drew. We're going to find out the
most romantic, over the top way to tell somebody I
have a prenup ready for your sign.
Speaker 6 (08:28):
I appreciate that I need help with just.
Speaker 2 (08:30):
So many you could like dot your eyes with a
heart when.
Speaker 5 (08:34):
The ideas are already flowing. We're gonna start your happily
ever after when we do your awkward Tuesday phone call
right after this.
Speaker 7 (08:42):
It's awkward, it's Tuesday. It's awkward Tuesday phone call.
Speaker 5 (08:48):
I think we need to clarify something here before we
move on, because the listener on the phone, Drew asked
his girlfriend to move in with him.
Speaker 2 (08:55):
Yeah, that was a while ago.
Speaker 5 (08:57):
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.
Speaker 2 (09:10):
Yeah.
Speaker 6 (09:11):
Yeah.
Speaker 5 (09:12):
Now, there was some people in the room who thought, oh, well,
maybe she was just joking when she said that. But
if I'm 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 6 (09:31):
I got the vibe that she was serious for sure.
Speaker 1 (09:34):
I hope so, because he went to a lawyer and
actually had one drawn up lawyers.
Speaker 2 (09:39):
Yeah.
Speaker 5 (09:40):
Now, so Drew needs our helped to bring it up
to her cause, 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
assets there. It's a tricky topic, and that's why I
(10:04):
feel like the safe thing to do is to give
it to someone who really knows about this. Jose, what
advice do you have for drew all.
Speaker 2 (10:10):
Those long relationshipesus?
Speaker 4 (10:13):
Okay, one time it lasted eight months, Broke, don't make
fun of me, all right, Okay, this entire conversation can't
just be about the prenum or it's gonna sound like
a downer, right.
Speaker 5 (10:24):
You need to.
Speaker 4 (10:25):
Hide it in between the wedding and ring shopping and
then the prenum.
Speaker 2 (10:30):
Seriously, think have important news.
Speaker 5 (10:34):
Distract her with shiny promises that will only work on Jose, Okay,
shopping and theory.
Speaker 6 (10:42):
Sure it sounds kind of sneaky, I don't know, man
like sneaky.
Speaker 4 (10:46):
But legally you still mention it.
Speaker 5 (10:48):
It's a terrible idea like that A little bit about
the engagement in the future. But Brook, what do you think?
Speaker 1 (10:54):
I think you you make sure that you frame it
as you are doing something for her.
Speaker 2 (11:00):
You say, listen, you said that you wanted this done.
I did it. Some people, you know, all talk, but.
Speaker 1 (11:07):
I'm a doer and that's how I'm gonna be in
this relationship.
Speaker 2 (11:10):
If you want something done, I'm the guy to get
it done.
Speaker 5 (11:12):
Look it, I'm doing stuff for you. What have you
ever done for me? Maybe you should sign this prema.
That's a good idea.
Speaker 2 (11:21):
Me to frame it that it's her idea.
Speaker 5 (11:23):
Yeah, guilter into signing it? All right? What do you think, Drew?
Speaker 6 (11:26):
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 you be.
Speaker 1 (11:34):
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 5 (11:41):
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 (11:49):
That's not going to end well for him.
Speaker 5 (11:50):
But sure, that was Brooks advice. So here we go.
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 8 (11:59):
I hope.
Speaker 2 (11:59):
I'm so romantic.
Speaker 6 (12:03):
I'm so nervous.
Speaker 5 (12:04):
We wish you a lot of luck. You don't be nervous.
We're all here to support you. Okay, yes, thanks, all right,
here we go down on your number right now.
Speaker 6 (12:19):
Hello, Hey, cal.
Speaker 8 (12:23):
Hey, what's that babe?
Speaker 6 (12:25):
How's your day? Your work?
Speaker 4 (12:27):
Yeah?
Speaker 8 (12:27):
Yeah, it was fine. It was just some normal you know,
the usual.
Speaker 6 (12:32):
Yeah, usual stuff. Do you have a minute? You give time?
Are you visier?
Speaker 5 (12:37):
Yeah?
Speaker 8 (12:37):
I can take a second.
Speaker 1 (12:38):
What's up?
Speaker 6 (12:40):
I wanted to ask you something. Remember that day we
had that conversation we talked about moving in. Do you
remember that vague? Yeah? I think I said no, right, yeah,
and which is fine, you know he said no. But
it got us talking, right, I got us talking about
(13:01):
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 8 (13:11):
Yeah, I mean I was like more than cute. I
think it was kind of important, like put us on
a new path together.
Speaker 6 (13:19):
Mm hmm, yeah, I agree.
Speaker 8 (13:24):
Why are you being so weird? What do you mean
you agree? No?
Speaker 6 (13:27):
I mean I just I just wanted to bring up
what you had mentioned when I asked you to move
in with me. If you remember, do you remember anything
about the agreement?
Speaker 8 (13:40):
You might have said, well, I just said I don't
want to move in with you until we get married,
like I told you that.
Speaker 6 (13:48):
Yeah, you said another word?
Speaker 8 (13:51):
Also, what's going on?
Speaker 6 (13:57):
Can you just say you know what? You know the
word I'm talking about? Can you just it just helps me?
And you know my anxiety?
Speaker 8 (14:03):
And I don't right now, So I'm gonna need.
Speaker 6 (14:05):
You to say it. It's it starts with the P,
you know what I mean?
Speaker 8 (14:13):
What's it ends with.
Speaker 6 (14:17):
Uprea?
Speaker 8 (14:19):
Okay?
Speaker 6 (14:20):
Yeah, okay, so you did say that. Great, Okay, is
there other No? 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, and.
Speaker 8 (14:44):
Just say lawyers. You hired a lawyer.
Speaker 6 (14:47):
Yeah, you know it's it's not legal beagle stuff, you
know what I mean? Like you kind of have to
when you do this.
Speaker 8 (14:53):
I don't know what you're talking about right now. Can
you get to the freaking point?
Speaker 6 (14:56):
So I don't want you to get upset. This is ridiculous.
So I 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 8 (15:12):
What do you mean you want me to sign it?
Speaker 6 (15:15):
This is your idea? Remember, this is your idea. This
is fun.
Speaker 8 (15:21):
This is just like a weird phone call. I feel
like you could have talked to me in person about this.
Speaker 6 (15:27):
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 rest.
Speaker 8 (15:35):
The radio station, what.
Speaker 2 (15:40):
Team radio people? I always wanted to hang up at
that point. I don't want to be here.
Speaker 5 (15:47):
I feel like it probably went just about as well
as their first conversation about.
Speaker 8 (15:50):
I don't understand what's happening right now, lawyers.
Speaker 2 (15:56):
That makes it sound like a joke. We don't want
to do that.
Speaker 5 (15:58):
We're reading show. This segment is called an Awkward Tuesday phone.
Speaker 1 (16:02):
Call, oh man, and we really emphasized that title today.
Speaker 5 (16:06):
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 8 (16:14):
Uh huh.
Speaker 1 (16:15):
Apparently 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 8 (16:22):
Well yeah, I said that, but he never like talk
to me about pursuing it and hiring lawyers and filling
out paperwork.
Speaker 5 (16:29):
Yeah, he should have written it all up himself. I
do agree with that, But no, Jeffery, Oh my god.
Speaker 2 (16:40):
I mean I can't tell what your emotion is right now.
Maybe it's just shocked.
Speaker 5 (16:43):
Didn't you want this?
Speaker 2 (16:44):
Maybe you don't care, maybe you're mad. Where are you at?
Speaker 8 (16:47):
I'm just like in the middle, really because I just
wish he was more honest and I feel like we
could have looked on it together.
Speaker 2 (16:54):
Okay, yeah, all right, So that's not bad.
Speaker 6 (16:57):
I mean that's I mean honest. This wasn't one hundred
sent 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 1 (17:09):
What it wasn't our idea for you to hire a
team of lawyers.
Speaker 2 (17:12):
You called us way after that, you.
Speaker 5 (17:14):
Emailed us, Drew.
Speaker 6 (17:15):
I just wanted to do a love shout out to
show I care about my my girl.
Speaker 7 (17:20):
Oh right.
Speaker 5 (17:22):
You know what, did I screw that one up again?
Speaker 2 (17:27):
The world's longest shutout.
Speaker 5 (17:29):
It's three hundred and eighty seven mistakes since yesterday. I'm
never going to get this job right. I'm sorry, Drew,
My bad for misunderstanding your awkward Tuesday phone request. Shout
out yes, excuse me again? Three?
Speaker 8 (17:45):
Wait?
Speaker 2 (17:45):
Does that mean you're still wanting her to sign the prenup? Drew?
Speaker 6 (17:48):
I don't want you guys to pressure her to go
ahead and want to sign it, that's for sure.
Speaker 4 (17:54):
Yeah, sorry about that.
Speaker 2 (17:56):
I was actually on the other band. I sign it,
but Alexis's fault. Yeah, I know so much about preanup.
Speaker 3 (18:02):
Sorry?
Speaker 2 (18:07):
Would we hire a twenty four hour I love she
brought it up.
Speaker 5 (18:11):
Yeah, we thought we would roll with it as long
as you two are good, right, Yeah.
Speaker 8 (18:18):
I think we'll figure it out.
Speaker 5 (18:19):
Maybe have a couple more talks about this.
Speaker 6 (18:21):
Yeah, we'll go on a camping trip and ride the
jeep top down or something.
Speaker 5 (18:25):
Everything's better top down in a jeep.
Speaker 2 (18:29):
Seems way more chill than you, Drew.
Speaker 5 (18:31):
I think she's confused.
Speaker 2 (18:34):
Love, that's something we can shout.
Speaker 5 (18:39):
Out successful awkward.
Speaker 6 (18:42):
Tuesday, freaking Jeffrey in the morning, I.
Speaker 1 (18:46):
Mean, then, who said romance wasn't dead? Greenups before moving in?
Speaker 2 (18:53):
That's a lot for anything.
Speaker 4 (18:54):
Yeah, I think in today's society this is good for legalities.
I'm gonna put this in my tender bio.
Speaker 5 (18:58):
If you swipe right, you agree to a prenup.
Speaker 1 (19:04):
A lot of problems and then you could put in
little tidy words all the stuff that she owes you.
Speaker 2 (19:09):
Yeah. Yeah, you're like, you didn't read the terms and conditions.
Speaker 1 (19:13):
That's on you, my man or my friend or Mike girl,
whoever you end up datingbody. And we did get a
lot of comments already from this Awkward Tuesday.
Speaker 2 (19:22):
Yeah, prenups always have mixed responses. Yeah, but I just
threw my wedding ring offs. Oh just have his own
will my bad? I'm not a prenup later Awkward Tuesday.
Speaker 3 (19:38):
Yeah, anyways, a lot of people saying prenup before proposing.
Speaker 2 (19:41):
That's crazy. In the place of it, it.
Speaker 5 (19:43):
Should be a long conversation.
Speaker 2 (19:45):
Were moving in a lot.
Speaker 3 (19:46):
Of red flags, you know, yeah, a little words.
Speaker 2 (19:49):
I'm not going to read that. There's mean words. It's
hard already.
Speaker 1 (19:53):
All right, leave your comments, thank you for being here,
and we'll be back tomorrow with another second date update
right here on. You know, we're going to call it
your favorite podcast, just because we want to lie to ourselves.
Let's call yeah, subscribe and share. It's Brook and Jeffrey
in the Morning
Speaker 2 (20:06):
Brook and Jeffrey in the Morning,
Hosts And Creators
Brooke Fox
Jeffrey "Young Jeffrey" Dubow
Jose Bolanos
Alexis Fuller
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