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August 12, 2025 19 mins

One of our listeners was FORCED to talk about money with his crush, and the reason WHY it’s the topic of conversation might be the craziest part. It's your Awkward Tuesday Phone Call podcast!

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Speaker 1 (00:00):
All right, welcome to the show with Daddy Issues. Hey,

(00:02):
oh yeah, it's Burke and Jeffrey.

Speaker 2 (00:04):
In the morning, there was a Second Date podcast, of course,
I'm referring to yesterday's Second Date where the guy said
because she had a nose piercing.

Speaker 1 (00:10):
As I'm staring at Alexis's.

Speaker 2 (00:12):
Nose piercing, which I had mine peers for eighteen years.
The only reason I took it out is because when
I was breastfeeding my baby when she was little, she
kept ripping it out of my nose.

Speaker 1 (00:25):
Oh my god, it hurts so bad. Oh yeah, yeah. Anyway,
my dad was all about it when I got it done,
but I'm.

Speaker 3 (00:33):
Already probably you as well. Yeah, it's like double pain.

Speaker 1 (00:36):
Yeah, it was double pain. Some of the comments we're
seeing from yesterday, yeah, kind of the same. Megan Jones said,
I got my nose piers with my dad. Oh yeah.

Speaker 2 (00:45):
Michelle says, everyone knows the universal sign for daddy issues
is a lower back tattoo. Yeah, it's just the universal
sign that you went to high school in the late nineties,
everybody had or a palm tree or a heart.

Speaker 1 (01:06):
Yeah. Yeah. I used to go to a tanny bed,
which don't do. By the way, it's terrible for you.
In the back of a video store. It was so sketchy,
that is, it was so sketchy.

Speaker 2 (01:16):
Anyway, we're got awkward Tuesday right now, and so let's
get awkward and make it happen.

Speaker 1 (01:21):
It's brand new and it starts now.

Speaker 3 (01:23):
The most uncomfortable topic to bring up in any conversation
isn't politics or religion or that hairy growth on your
lower back hands down? Its money? Oh oh yeah, top.
And while it's kind of unavoidable if you're talking with
your boss or your roommate, the last person you want
to bring it up with is your crush.

Speaker 1 (01:45):
Ooh, I know.

Speaker 3 (01:46):
That's exactly what one of our listeners is being forced
to do. And the craziest part is why he has
to discuss it with her. Oh, it's so weird. You're
going to hear it in your brand new awkward Tuesday
phone call right after this. It's awkward.

Speaker 1 (02:03):
It's Tuesday.

Speaker 3 (02:05):
It's awkward Tuesday phone call. It shouldn't happen, but sometimes
it does. Where money comes between friends and ruins their
relationship forever.

Speaker 1 (02:16):
Yeah, so easily that can happen.

Speaker 3 (02:19):
Yeah, like when I bought Brooke a seventy dollars wine
glass to Canter for her wedding. That should pretty much
equal out Brooke paying for all of my lunches over
the last decade, but somehow she doesn't see it that day.
Why you don't pay her?

Speaker 2 (02:34):
I actually got married thirteen years ago, so it's been
over a decade that I've been paying for lunches.

Speaker 3 (02:39):
That's three years. You see the hostilities that I'm still
getting over a decade later. Now, Brooke and I've been
able to work through it, but one of our listeners
hasn't had as much success with his friend, and that's
why he needs our help today. Nick, Welcome to the
friend Dome. How you do it?

Speaker 4 (02:59):
Hey, guys, if you're having me, do you? Nick?

Speaker 5 (03:05):
Now?

Speaker 3 (03:06):
Not yet? Well, tell us about the situation going on
that's created issues with you and your friend.

Speaker 4 (03:13):
Yeah, so I got this co worker. She works in
my company, but different floor, so I don't really see
her that much.

Speaker 1 (03:21):
So this is just a work friend that we're talking about.

Speaker 4 (03:24):
Yeah. Yeah, so I've had like a small crush on
her for a while.

Speaker 3 (03:28):
Okay, what's her name?

Speaker 4 (03:31):
Yeah, Dana.

Speaker 1 (03:33):
Okay, does Dana know you have a crush on her.

Speaker 4 (03:36):
She does because I actually asked her out in a
work event at a year ago.

Speaker 3 (03:40):
Okay, how long ago?

Speaker 4 (03:44):
About a year ago?

Speaker 1 (03:45):
A year ago, so it didn't turn into anything.

Speaker 4 (03:48):
Now, she actually had a boyfriend at the time, so
she said no, thank you, but I would if I
wasn't in a relationship, so she was nice about it. Yeah.
So a year later, I'm kind of out of the blue,
I get a message from her and she wants me
to meet her outside. And we have food trucks outside

(04:09):
of our buildings, so she asked me to come meet
her outside by the food truck. So excited, I'm like,
I've always liked this girl. You know, I'm still single,
so maybe something exchanged.

Speaker 1 (04:17):
Oh yeah, maybe she broke up with her boyfriend. Yeah
you know.

Speaker 4 (04:20):
Yeah yeah. So turns out she needed a plus one
for a wedding that she was going to that Saturday.

Speaker 6 (04:26):
Wow, wedding dates a legit invite.

Speaker 1 (04:30):
That is her opening, right, just single.

Speaker 4 (04:33):
Then at the time, I wasn't sure, and I really
didn't want to ask that question.

Speaker 2 (04:37):
Oh yeah, I feel like if I don't ask and
I don't have to know.

Speaker 4 (04:41):
Right, Yes, I wasn't sure, and uh, I just kind
of wanted to find out and see, and I legitimately
could not say yes quick enough.

Speaker 2 (04:50):
I'm still hoping she's single, and so I can say, oh, yeah,
so have you.

Speaker 3 (04:55):
Gone to the wedding yet or no?

Speaker 4 (04:57):
Yeah, so I canceled my plans. I was excited to go.
Oh I had plans already.

Speaker 3 (05:01):
But they can wait totally right.

Speaker 4 (05:03):
So I went to the wedding, and I did find
out that they broke up.

Speaker 3 (05:06):
Yes, horrible. You're talking about Dana and her boyfriend.

Speaker 4 (05:13):
Yeah, dated her boyfriend.

Speaker 3 (05:14):
Dude, that's awesome and lining up for you.

Speaker 2 (05:16):
I feel like you had to like restrain yourself when
she said yeah, we broke up, You're like, oh, pump
under the table.

Speaker 4 (05:24):
I pretended to feel sad about it.

Speaker 1 (05:26):
Good job, what you're supposed to do.

Speaker 4 (05:29):
Yeah, And we had a great time. And it was
our friend from college's wedding. We were dancing, drinking, had
a flirty vibe between us.

Speaker 6 (05:36):
Oh good, Yeah, this is random, But like, how were
you associating with her other friends?

Speaker 3 (05:41):
Yeah? I guess that they will give you a good
read into how there will, like the vibe is between
you and her, if you're able to get along with
her friends mutually, yeah.

Speaker 5 (05:50):
Yeah.

Speaker 4 (05:50):
We were all drinking at the bar, having a good time,
good great size.

Speaker 1 (05:53):
Okay, where does the money sign?

Speaker 2 (05:56):
Like? This is feeling like a second date update, not
a for Tuesday.

Speaker 4 (06:00):
Oh I'm getting there, don't worry.

Speaker 1 (06:02):
Oh you're life Okay.

Speaker 4 (06:04):
At the end of the night, we had a hug.
I could have went for the kids, but I didn't,
you know, out of disrespect. We were drinking and I
answered to hang out next weekend and she said she
would really like that.

Speaker 1 (06:13):
Cool.

Speaker 3 (06:13):
Okay.

Speaker 4 (06:14):
Then two days later it happened.

Speaker 1 (06:17):
What did who?

Speaker 4 (06:20):
I got a Venmo request asking for one hundred and
fifty dollars to cover my wedding guest feet?

Speaker 1 (06:26):
Oh what from who? It wasn't from her? It was
from her?

Speaker 4 (06:31):
It was from It was from Dana.

Speaker 3 (06:32):
Yeh wow, I've never even heard of that.

Speaker 1 (06:35):
Did she Venmo the wrong person?

Speaker 4 (06:37):
I texted her and I said, are you sure this
is for me? I thought maybe it couldn't be for me,
and she said it's from both of us.

Speaker 3 (06:44):
We will wait wait, so we will.

Speaker 2 (06:46):
I guess it makes sense if the bride didn't like this,
she didn't bring a boyfriend, he said, wedding gift. It
sounds like there that she's making him pay for the.

Speaker 1 (06:54):
Wedding gift that she gave her friend from college.

Speaker 3 (06:58):
Is that what you said? Gift?

Speaker 5 (07:00):
Know what?

Speaker 4 (07:00):
Yeah, wedding costs, guest cost guest wedding.

Speaker 1 (07:04):
Guess what is that? Then?

Speaker 3 (07:06):
I'm not sure to be okay, So what is it
that you want to do with your awkward Tuesday phone
call that?

Speaker 4 (07:13):
I mean, I kind of just want to know what
the costs are for? Why am I paying them? Yeah,
you invited me to a wedding, Like she's hugely like,
I want to know what's going on.

Speaker 1 (07:23):
It's like her okay, I.

Speaker 3 (07:24):
Mean, it would make sense if he was getting an
invoice from the bride and groom directly and that was
their issue, But the fact that it's coming from Dana
that makes it really really weird.

Speaker 2 (07:34):
Well, and there's no explanation. She's treated that like that's
an obvious Like yeah.

Speaker 3 (07:39):
Like she said for food or for a give or.

Speaker 2 (07:42):
Maybe there was like a cash bar and you didn't
realize oh yeah, you know, like maybe the drinks cost
that night.

Speaker 4 (07:48):
Maybe.

Speaker 3 (07:49):
But he wants to keep the chance of a romantic
connection alive. So we're going to come back and figure
out some ways to flirtily sexily ask her about Hey,
what's the one hundred and fifty dollars charge? He sent me?

Speaker 6 (08:00):
All about flirty conflict this you, Jeff.

Speaker 3 (08:04):
Yeah, we'll come back with some advice for you for
your awkward Tuesday phone call right after this. It's awkward.
It's it's awkward Tuesday phone call. If you're just joining
us for the awkward Tuesday phone call not only as
a friendship on the line, but a possible love connection
between our listener Nick and his coworker Dana. There's been

(08:27):
some unspoken feelings happening there. So when she asked him
to be her plus one to a wedding recently, that
was his golden opportunity.

Speaker 1 (08:36):
Oh, he was so excited.

Speaker 3 (08:38):
The weird part is afterwards, Dana sent him a one
hundred and fifty dollars invoice to cover their wedding guest fees.

Speaker 1 (08:46):
We still don't know what that means.

Speaker 3 (08:47):
Nobody knows what that means, least of all Nick, and
it just felt wrong to him because he was the
plus one. He didn't even know who the bride and
groom were. That's why he wanted our help today to
bring it up to Dana. And figure it out while
still keeping his chances with her alive. Honestly, though, Nick,
if you really want this woman to like you, maybe
the best answer is just eat that one hundred and

(09:10):
fifty dollars and don't make this phone call.

Speaker 2 (09:12):
I was gonna say no, you guys, this sets the
tone for the entire relationship.

Speaker 1 (09:17):
Honestly, he takes care of his lady.

Speaker 3 (09:19):
Yeah, she'll like that about you. Yeah, okay, Brook, you
have better advice for him? What's do?

Speaker 1 (09:24):
I think you should get out of pen and write
down my question right now? Seriously, Brook, nobody writes with
pen and paper.

Speaker 2 (09:29):
Just write on your phone and okay, okay, I need
to ask her, Nick, why pay her half?

Speaker 5 (09:35):
Oh?

Speaker 1 (09:36):
Yeah, seriously? Why pay her half?

Speaker 2 (09:38):
Because she said that it's for me as well. Right,
so she invited you, it's her friend. Sure she should
be paying for you.

Speaker 1 (09:48):
But but in the least, why do you have to
pay her wedding fee? That doesn't make any sense.

Speaker 3 (09:53):
Are you saying that on a date? Brook? You wouldn't
make your husband Michael pay for stuff.

Speaker 1 (09:57):
This isn't a date.

Speaker 2 (09:58):
This is a wedding and this is her friends like
bridy grooms do weird things.

Speaker 1 (10:03):
All the time.

Speaker 3 (10:06):
When you and Michael are at a wedding, all bets
are off. You guys aren't together, you have separate entities,
and whatever happens just happened. I see what you're saying.
B take that in mind, Jose, what's your advice?

Speaker 1 (10:19):
I don't understand.

Speaker 6 (10:21):
I get it, Jose, you are going to do something
really unconventional here. Okay, you're gonna thank her immediately?

Speaker 1 (10:28):
Really?

Speaker 2 (10:28):
Why?

Speaker 3 (10:28):
Oh yeah?

Speaker 4 (10:29):
Why why would I think her?

Speaker 6 (10:30):
Well this, it's a positive tone. Immediately you're like, hey,
thank you so much for that. I didn't even think
to ask if I owed you any money? And then
maybe guess what you think it's for.

Speaker 3 (10:40):
Rather than accusing her of what it's for, you're like
disarming her with a compliment before you come in with
the real question. Oh my gosh, I must have.

Speaker 6 (10:49):
Yes, it must have been a wedding gift.

Speaker 2 (10:51):
I mean, it could get you the answers you want
of what it's for, but it definitely doesn't get you.

Speaker 1 (10:56):
Out of pain for it.

Speaker 6 (11:00):
One step at a time, for happy, keep the vibes positive.

Speaker 3 (11:03):
What do you think you feel like that's helping you out?
Before you make your.

Speaker 4 (11:06):
Call here, yeah, I guess I'm still very confused on
why I got a bill. I guess I would all
figure out in the moment.

Speaker 3 (11:13):
But we've given you the tools to be able to
hopefully handle this conversation without making it too awkward between
you and Dana.

Speaker 2 (11:19):
I'm so curious how you're going to feel after you
hear her answers, And I.

Speaker 1 (11:24):
Wonder what the is seven five each is a pretty
good deal for a wedding, just.

Speaker 3 (11:27):
Saying you're lucky that she didn't invoice you to pay
for her dress also, so count your blessings. But we're
going to dial her number right now. Hopefully she picks
up and you can make your awkward call. But here
you go.

Speaker 4 (11:48):
Hello, Hey, Dana, it's Nick. How you doing.

Speaker 5 (11:52):
Hi, Nick, I'm great, It's great to hear from you.

Speaker 4 (11:55):
You too. How's everything going.

Speaker 5 (11:58):
It's going pretty well. Just working like usual, as you know.

Speaker 4 (12:02):
Yep, yep, just another day on the grind.

Speaker 5 (12:08):
What we do. So what's up? Are we still getting
together for lunch today?

Speaker 4 (12:12):
Or yeah? Yeah? I mean I had a great time
the other night, and I want to thank you first
for the invite in the party. I had a great time,
and I just I kind of apologize for not asking
what I owed for the event, because I know I
got that invoice, so I didn't know. I wanted to
find out more like what's going on?

Speaker 5 (12:31):
Oh yeah, well you know the bride she sent me
an invoice and actually charged me seventy five dollars for
each of us. Oh wow, you probably wanted to know that.

Speaker 4 (12:42):
Yeah, I just kind of came out of nowhere. When
you go to a wedding, you don't you know someone's
taking you, you don't really think about paying. So but
I also just I should have asked if I, you know,
owed anything, because I love hanging out with you, and
you know, I never want to chalk in between that,
you know.

Speaker 5 (12:58):
I mean maybe I read the situation wrong. I mean
I kind of thought that we were on a date,
and typically whenever I go on dates, guys will usually pay.
Are you saying you wouldn't want to pay if we
were on a date.

Speaker 4 (13:11):
I was a date, I think it would be different.
I just kind of you kind of invited me, and
I didn't know if it was you were considering it
a date or if it was I don't know, just
kind of came out of left field. A little context
probably would have helped. You know.

Speaker 5 (13:23):
Oh that's interesting. It kind of feels like you're criticizing
how I handled it.

Speaker 4 (13:29):
Not trying to criticize, just kind of thinking out loud
and just trying to get some more information. You know.

Speaker 5 (13:35):
Well, ever, since I broke up with my boyfriend, I've
been on quite a few other dates, and guys are
just notoriously cheap, And that's why I'm just so glad
that I'm getting to spend time with you. You know,
you have so much integrity and you really know how
to treat a woman.

Speaker 4 (13:49):
Well, I appreciate that.

Speaker 5 (13:52):
So if you wanted to spend more than one hundred
and fifty, you know, I did have to uber home
that night, and there were just a couple other expenses.
Oh man, Nick, you're not saying a lot. Is there
a problem? Like what's going on?

Speaker 4 (14:08):
So? Uh, that's a little that's a little outlandish, that's
a little crazy.

Speaker 5 (14:16):
It's outlandish. Is Atlantis to want to take care of
me to make sure that I get home safe? Like
you wouldn't just want to spend a little extra money.
Maybe you're not the person that I thought you weren't.

Speaker 4 (14:25):
Nick.

Speaker 2 (14:26):
Oh god, god, Nick, that is terribless.

Speaker 5 (14:35):
No, not, Hey, what's going on?

Speaker 1 (14:38):
Who is that?

Speaker 4 (14:39):
Hell?

Speaker 1 (14:40):
That was so manipulative, Dana.

Speaker 3 (14:43):
We're all very impressed with you, Dana, because, yeah, you're
on a radio show right now called Brook and Jeffrey
in the.

Speaker 2 (14:50):
Morning, a radio show.

Speaker 1 (14:53):
Yeah, Nick's there too.

Speaker 5 (14:55):
Nick, Why would you do this?

Speaker 2 (14:56):
This is between you and me.

Speaker 5 (14:57):
Why would you call a radio show? What is happening?

Speaker 4 (15:01):
It just kind of was taken off guard. I was
kind of confused on the whole situation, and I needed help.
I called them to help me because I really like
you and I wanted to continue our relationship and I
didn't want to make it awkward.

Speaker 5 (15:11):
So, yeah, you don't like me enough to pay for
my uber to get home safe, So I guess that's
clear enough.

Speaker 1 (15:18):
Or even go to the wedding and uber home regardless.

Speaker 2 (15:20):
There, dam How does that have any indication of whether
or not he likes you.

Speaker 1 (15:24):
You guys work at the same place. You probably make
around the same amount of money, like pay for yourself.

Speaker 5 (15:30):
First of all, I don't know who the hell you are.
And certain women have standards. It sounds like you have none.

Speaker 1 (15:37):
No, certain women have independence, and you need some.

Speaker 5 (15:40):
Excuse me, No, do you know what year it is, Grandma.
Women are still to be taking care of.

Speaker 2 (15:46):
Taking care of Okay, we're back into the nineteen ten.

Speaker 3 (15:49):
Is enough of to pull yourself up by your own bootsteps.

Speaker 1 (15:52):
It's not that pay for. You invited him to the wedding.

Speaker 3 (15:56):
Let us puts we want to lift you to greatness.
That's what tells me.

Speaker 4 (16:04):
Okay, hey, so yeah, these people were trying to give
me a hand. But you know, I'm sorry, Dana. I
want to take responsibility for it.

Speaker 2 (16:11):
You know.

Speaker 3 (16:12):
Yeah, that's nice, that's really nice.

Speaker 4 (16:15):
I could have been better.

Speaker 1 (16:16):
Yeah, Now, why are you taking blame for this?

Speaker 4 (16:21):
I mean, Brook, you're ganging up on her. You're getting
up on the team, and me, I came here as
a guest. I don't have to put up with this.

Speaker 3 (16:28):
Up for you, No, he does. He wants to stand
up for Dana because he was her date.

Speaker 1 (16:33):
Yeah, and so at the beginning, this is what you want.

Speaker 5 (16:38):
That is how women should be treated. Thank you, Nick.

Speaker 3 (16:40):
Okay, we'll start. I'll come into an agreement here. So
at the start of this I suggested you eat one
hundred and fifty dollars, but it sounds like you need
to do a little bit more to how much money
are you willing to cost towards her and venmo to
prove how good of a date you are?

Speaker 4 (16:54):
Whatever she needs to feel comfortable here.

Speaker 3 (16:56):
Wow, you just want a good guy.

Speaker 2 (16:58):
You're just buying her affection at this point. That is
not worth it.

Speaker 1 (17:02):
It won't last in the end.

Speaker 3 (17:03):
Brook, you're not dating anymore. I don't think you have
any You you checked out thirteen years ago from this
ral with my seventy dollars wine decant. That's payment for that.

Speaker 2 (17:15):
So you know after this, I'm venmoing you a charge
for attending my wedding and that's just Nick.

Speaker 3 (17:21):
You're going to cover that cost from me, right, Bro,
it's about love.

Speaker 4 (17:25):
I don't have you, but I do have Dana. Dana,
You and I are good.

Speaker 3 (17:28):
Oh wow, what a gentleman, Dana. You landed a good
one there. Yeah, chivalry Ison dead?

Speaker 1 (17:33):
What romos?

Speaker 4 (17:34):
Nick?

Speaker 5 (17:34):
Don't listen to him. I'll see you at lunch. You're
paying Okay?

Speaker 2 (17:37):
Now, you actually do sound like Jeffrey.

Speaker 3 (17:41):
You should be so lucky.

Speaker 2 (17:43):
Brook.

Speaker 3 (17:43):
It Jeffrey in the morning, and we don't have Dana
on the phone with us anymore. But it sounds like
Dana was used to more of the traditional style of
a relationship where all the men are expected to pay
for dates, and that's not what everybody wants, but it's
probably how she was raised and what she is hoping
for in a relationship.

Speaker 2 (18:03):
It just sounds like she's cheap to me. She doesn't
even pay her own bill at or friend's wedding. I
think that she knew that her friends were going to
charge for that wedding and she had she had to
find the sucker to pay for it.

Speaker 1 (18:14):
Yeah, that's what I think.

Speaker 3 (18:16):
That's possible. Sure, or it could just be like she
was saying, that's how she was raised and that's what
she expects from a guy.

Speaker 1 (18:24):
Consider a date too.

Speaker 3 (18:25):
Yeah, date, He wasn't sure, but he heard Dana's explanation
and then he eventually came around on it.

Speaker 1 (18:31):
He eventually came around coward coward.

Speaker 3 (18:35):
To her, like every woman wants a good man to
do absolutely so, as long as expectations are laid out
ahead of time, it's really up to Nick to say
yes or no.

Speaker 1 (18:47):
Well, he does finally know and we did help him
with that.

Speaker 3 (18:49):
Yeah, for sure, because it's his life and he chose
to pay for it and for her life. Too, and
that's true happiness. So hopefully we helped him achieve something
that he felt was positive.

Speaker 1 (19:01):
I'm glad you're taking such a noble stance on this.

Speaker 3 (19:03):
Well, you know, I'm just trying to play the middle. Yeah,
so we'll try to do that for you. If you
need help with your awkward lives, email the show, and
if you haven't already, hit subscribe on that subscribe button.

Speaker 1 (19:14):
Thank you.
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Hosts And Creators

Brooke Fox

Brooke Fox

Jeffrey "Young Jeffrey" Dubow

Jeffrey "Young Jeffrey" Dubow

Jose Bolanos

Jose Bolanos

Alexis Fuller

Alexis Fuller

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On Purpose with Jay Shetty

I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

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