LAURA STASSI

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I'm Laura, and this is Dating While Gray, the grownups guide to love, sex and
relationships. On this episode, we're talking about that thing we may have grown up
believing we're not supposed to talk about: money.

I signed up for a webinar called Dating After 50 with Bella, who calls herself an expert and
a love guru. According to Bella, the key to a successful first date, at least for straight
couples, is that the man should always pay for it because it makes the woman feel special.
But the woman should always offer to split the bill because the man is evaluating the
woman's potential as a supportive partner. Now, this advice seems sexist and old
fashioned to me, but hey, it's Bella who's the expert love guru, so whenever I want on a
date and the bill came, I'd start fumbling around for my wallet. My date would notice and
say, "I've got this." And I'd say, "are you sure? Happy to split." And he'd say, "I'm sure," and
he'd pay. But then along came, let's call him Gary, a man I met through a mutual
connection. Gary asked me out to dinner, chose a restaurant and made the reservation.
And when the bill came, I started my wallet fumbling routine. Gary noticed, but he did not
say, I've got this. He said, "we can do one of two things. I can pay this time, and you can
pay next time, or we could split the bill." Okay, reasonable, but not what I was expecting.
We split the bill and then we split the bill the next three or four more times after that. I
really tried to see Gary as a potential romantic partner because I really like the mutual
connection who set us up. But because we always split the bill, it felt more like Gary just
didn't want to eat alone.

The love guru was right. I didn't feel special. If Gary had offered to pay, I might have
overlooked the fact that we really had nothing in common. Gary and I disagreed about
politics. We disagreed about religion. And we disagreed about how and when to spend
money. For example, Gary saves up his vacation time so he can cash it in at retirement.
And when Gary and his wife separated, Gary set up a cot in his office and lived rent free
for six months. Me? I fork over money for vacations and places to live. Maybe oops! Spend
more than I've managed to save because carpe diem, baby! Nothing wrong with Gary's
choices and nothing wrong with my choices. They just are not compatible. You know, until I
met Gary, I figured the most difficult aspect of re-coupling would be actually finding
someone I want to re-couple with, but now I understand that before I get too involved with
someone, I need to make sure we can agree on the decisions we make around money.
You know, that we're financially compatible. But figuring out that compatibility can be
awkward and it starts on the very first date. For me, paying for the first date means that
person is willing to invest in a possible future with me, but I recognize that's really unfair.
Dating is expensive, especially when it's likely that we're all going out with a lot of different
people before we figure out if any one person has relationship potential. When you look at
it that way, I totally understand why Gary wanted to split the bill. I just wish we had talked
about it before I ordered.

The question of who pays on the first date feels like it should be small, but there's all these
expectations that you haven't shared yet, or at least Gary and I didn't. And for some
people, all those unspoken expectations might be so daunting that they're extremely
cautious about dating. For a man I'm calling Ken, that feeling stems from his experiences
back when he was married.

KEN
When it really came to a head was when we were both out of work at the same time. It's
hard enough to be sharing a home both out of work. So I would let her stay home and look
for work and I would go to the library and try to look for work.

LAURA STASSI
Ken got married for the first time when he was 40. They had two kids and his wife became
a stay at home mom. And then when Ken was in his mid-fifties, he lost his job in a
company downsizing. And then he lost his home, couldn't afford the payments. And then
his marriage fell apart. His wife moved back to her home state to find a job, and she took
the kids. And then there were legal bills and divorce lawyer fees and child support
payments, even though Ken still didn't have a job. It's taken Ken a long time to recover. I
asked him how this experience has affected his dating life.

KEN
It has caused me to become very selective in how I spend my time and money. I've
learned to spend more of my time socializing through meetup groups.

LAURA STASSI
Right.

KEN
And what has been helpful about that is that each person that I mean, I suppose it's
possible that might, men might still buy woman a drink at the bar there or something. By
and large, each person has to pay their own way.

LAURA STASSI
Right.

KEN
I am coming into a second pension I'd gotten, so I'm looking forward actually having
money to actually really start dating again.

LAURA STASSI
Do you ever want to say, "hey, I'd like to go out to dinner? How do you feel about going
Dutch?" Or is that?

KEN
Well, yes, I'm I'm really, I'm not sure how to do that. I'm not sure I have wanted to try to find
a financially independent woman.

LAURA STASSI
Right.
KEN
Where I think that kind of conversation would go over better and where they're not
expecting me to provide something which I can't. Used to be able to, but no longer can no
longer want to, feel I've given it the office. You know, be together if we both value each
other's time as opposed to there being some monetary component going on.

LAURA STASSI
Right. So charming and the wining and dining is, just takes a different form.

KEN
Well, I'm trying to, trying to navigate the waters here and figure that out. Does it? Can it?
Should it? How does one do that and so forth.

LAURA STASSI
Do you have a fear of actually getting in another committed relationship where you would
be co-responsible, I guess? I mean, with couples, you've got two people coming together
financially, but that means if something happens with one of them, the other one, you
know, sort of takes responsibility.

KEN
Well, right. I mean, certainly, I mean, in marriage, you know, merging of checking accounts
and so forth and assets. But I don't think that's appropriate other than in marriage. I want
to make sure that someone wants to be with me, not with my money. Have to try to figure
things out better, and try to understand people's true intentions. Well, I feel like I've been
burned in my marriage. Just as women can get hurt in a relationship, so can men,
emotionally and financially.

LAURA STASSI
Right.

KEN
You know, I'm trying to look beyond, you know, beyond the surface. I don't want another
train wreck in my life. So I have to find a, make sure that I avoid that. Keep the, keep the,
keep the train on the rails.

LAURA STASSI
So how, how would you envision that conversation going?

KEN
One of the things I may try, which I haven't really done much of, is online dating because
it's possible to specify. I think maybe on some dating web sites that, well you can certainly
let others know what your current retirement income, that you're no longer making
$200,000 a year and you can possibly look to see what their income is or certainly what
their, sometimes what their income expectation is. And if there's not a checkbox for a
financially independent woman, it's harder. But to search, but by looking through the
profiles.

LAURA STASSI
Right.

KEN
You can try to get a sense of that or not.

LAURA STASSI
Yeah.

KEN
It's not like you can just talk to somebody like you're conducting a job interview and ask
them.

LAURA STASSI
Right.

KEN
You know, give them a list of questions and have them answer them. So.

LAURA STASSI
What's your 401(k) like?

KEN
Right. Right. So I'm trying, I'm definitely trying to figure out who is financially independent,
is not looking to be rescued. You know, it's quite possible through the dating websites, too,
by specifying that one's looking to meet someone locally, too. It seems to me from what
I've seen, that's necessary or sometimes people think, oh, this is an opportunity to have
someone pay for my relocation to the national capital region. Or.

LAURA STASSI
Right.

KEN
So.

LAURA STASSI
So have you thought about what your first I mean, I'm assuming even if you meet
somebody online, your first date might not be dinner?

KEN
No, probably would be coffee to begin with. Maybe a hike after that. Trying to really low
key, keep it non-pressured. Inexpensive, and try to, cause, and try to figure out whether
there's any chemistry and mutual interests and whether it's, whether it's a match, whether
they seem to be financially independent and are not looking to, as you know, for a
relationship, as a source of income or, you know. So it's been about seven years. And so I
think there's something called the seven year itch. Maybe it's about time.

LAURA STASSI
Time to start scratching.

KEN
Right, exactly.

LAURA STASSI
So seven years after Ken’s divorce, and I'm still hearing a lot of caution in his voice. I can't
blame him. You heard him say he felt like he got burned in his marriage. I know it sounds
like a stereotype that men fear women want them only for their money. But I've heard from
lots of gray daters, men and women. And what I'm hearing is that we're all making a lot of
judgments, fair or unfair, when it comes to money.

CALLER 1
Hey Laura, I was calling about when to talk about money.

CALLER 2
Hi, Laura. As you know, getting a divorce is a gigantic financial burden. So after my
divorce, I was starting from scratch and rebuilding.

CALLER 3
Yes. Laura, I've got things around money, and my worthiness, and what I have to offer.

CALLER 2
I'm financially responsible for my young daughter, so I need to be very thoughtful and
prudent about my finances. And so I have started running background checks, complete
background checks, on people that I'm interested in.

CALLER 1
I don't know what it is about people in our age group who seem to want to pretend they
have a lot more money than they have.

CALLER 2
Typically, I've seen things with different bankruptcy, with different credit card disputes. So
the $30 a month I pay to instantcheckmate.com seems to be a wise, wise investment.

CALLER 3
Financially, I don't have what I need. Should have, not need. I believe I have all that I
need. And how that affects how I think someone would perceive me or how interested
someone would be in me.

CALLER 2
Well, I can understand how divorced men may have somewhat justifiable, spotty financial
histories. I use that as a litmus test.

CALLER 3
I don't know. Does it matter? Does it matter to men? You know, it just seems like it would
take a miracle.

CALLER 2
And I want someone who will understand that my wealth is passing to my daughter and
won't be shared in community with a partner.

CALLER 3
Hope this finds you well.

CALLER 2
Thanks, Laura. I'm enjoying the podcast. Good luck, bye.

LAURA STASSI
So how do we manage all of our worries about money so we can keep putting ourselves
out there? I'll look for answers after the break.
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I think gray daters may be especially anxious about money because we may have taken
financial hits like job loss and divorce and we have fewer working years to try to recover.
The idea of facing hard financial reality may make us squirm, but Colette Kolanko says it
doesn't have to. Colette's a CPA and a certified financial planner, and she says we can find
creative and loving ways to talk about money with a future partner.

COLETTE KOLANKO
I came together with my partner before I was age 50. However, when he proposed to me, I
said, "Honey, let's do our taxes and see what it would look like." And I turned, I finally
turned to and said, "Honey, I love you too much to marry you."

LAURA STASSI
How romantic.

COLETTE KOLANKO
And we made a conscientious effort to look at our finances and take that money that we'd
be paying to the IRS to do something together. So there's a way that you can take the cut
and dry and the nitty gritty of finances and taxes and bills, and, and you can turn it around
and you can make it a very joint experience. You can build a life and it doesn't have to be
adversarial or anything to be afraid of or ashamed of. I believe that you come together and
you look at this empathetically also.

LAURA STASSI
Right.

COLETTE KOLANKO
Especially the first, as you first start opening up to one another. One of the things that we
haven't really talked about was, is the income disparity with women. So sometimes it
doesn't make sense that even though the woman might want to come into the relationship
and say, "let's split things 50/50."

LAURA STASSI
Right.

COLETTE KOLANKO
It may really put a burden on her to come in with the expenses at 50/50.

LAURA STASSI
What should people 50 and older make sure they have going forward before they even
attempt to couple up?

COLETTE KOLANKO
Take a breath and see where you are. If you're going to have a dating budget, you may
want to think about where you can reduce your costs in other ways.
LAURA STASSI
Right.

COLETTE KOLANKO
Somebody might have champagne tastes and you may have a beer pocketbook.

LAURA STASSI
Right.

COLETTE KOLANKO
And it's okay to say, "this is not how I choose to spend my budget." Or, "can we do, you
know, this is great this time, can we do something else next time?" So that you can choose
something that is more in line with your budget. I truly believe that you need to protect
yourself both from a emotional level, but also from a financial level.

LAURA STASSI
Right.

COLETTE KOLANKO
I mean, that's part of who you are. And if you can't afford to do something, I think you owe
it to yourself and to the other person that you're doing this with to say, "this is just out of my
realm." Whether it's from a purely financial aspect or if it's you know, if you don't want to
spend that kind of money on your experience or your dating or your meal, that's, it's OK.

LAURA STASSI
You know, I spoke with one couple and I asked them at one point what is easier to talk
about, sex or finances. And the man immediately said sex.

COLETTE KOLANKO
There's a lot of divorces that happen because of finances. Right? So either they're fighting
about money anyway, and it brings out your, there are other underlying issues and it
comes out with fighting about money. Or, there are people who under certain
circumstances say, "we'll get divorced because of the need to, it's easier to manage
money separately."

LAURA STASSI
Should couples share their credit scores? Their salaries? Their debt? Their obligations?
What level of sharing do you recommend?

COLETTE KOLANKO
The answer is yes. When is the question. And again, it's got to, it's got to be individual. I
wouldn't recommend saying, "oh, my credit score is eight hundred," on your first date. But,
you know, things happen. I have a friend who's just been "widowed" and I'll put that in
parentheses, they were living together. And his partner had a lot of medical bills. And so he
took it upon himself to help provide for the, for his partner. Well, it affected him financially.
This couple was living together. And at that point in time, I think that you really should start
thinking about some kind of written documentation. Whether it's, you know, the first thing is
a cohabitation agreement that says kind of like a prenup, that's.

LAURA STASSI
So this is, excuse me, this is any couple who have decided to take the step and they want
to live together?

COLETTE KOLANKO
Right. It doesn't, it doesn't matter whether you are a gay couple or a straight couple. I think
that as you come together, because at that point in time, you're creating a partnership,
right? Of some sort. You're not just roommates. You are looking at being a partner. A
prenup and a cohabitation agreement is kind of like saying, "we plan on being together for
long term. But if something should happen, I want you to be treated with the same love
and honor and respect in the future as what we have today. So let's set that out today."
And I think it could be.

LAURA STASSI
That's beautiful.

COLETTE KOLANKO
I think it can really be something that's very loving and, and meaningful. And I think you
look at things as you're first coming together as a, as partners and you look at it differently
at year zero than you might at year five or 10 or 15. That's why you can, something like a
cohabitation agreement or a prenup agreement or a post-nup agreement. They can
change. Right? As long as you're alive and you're together, you can always update those,
those documents.

LAURA STASSI
Right.

COLETTE KOLANKO
I don't think it's ever too early or too late to rearrange the, your agreement on how you're
going to pay thing, pay for things, and not to be afraid to discuss this, because if you truly
care about someone, you're going to want to know, maybe you want to help. Or you, it's a
way to see how the other person reacts, and it's a just another level of your personality,
your commitment. And it's not something to be afraid of. So don't be afraid of that finance
talk. It can be done in a, in a very loving way.

LAURA STASSI
You know, I was married for almost 30 years. It's totally possible that I could have another
relationship that lasts as long as my marriage did. And that means some real financial
considerations concerning my kids, perhaps his. And whether it makes more sense to
have a cohabitation agreement or a marriage certificate or simply be committed
sweethearts living apart without any legalities whatsoever. In fact, after I talked with
Colette, I started thinking that the older you get, the more complicated your financial
history and picture might be. And so the more awkward and stressful the money
conversation gets. But that was before I met Bob and Marge.

There will NOT be a new episode of Dating While Gray next Thursday. But I WILL BE
sharing more on the Dating While Gray Facebook page. I usually post interesting articles
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AND I’ll answer some of your questions about the show and share some of YOUR stories.
Join the Dating While Gray community on Facebook. Just search for Dating While Gray
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Just when I think money is such a difficult topic, I find Bob and Marge.
BOB HOWARD
I’m Bob Howard. I'm 84.

MARGE LANE
I'm Marjorie Lane and I'm 86. And they call somebody like me a cougar, right? I was a
clinical social worker in private practice and I managed to be self-sufficient and save some.
So I had put aside for my old age what my financial planner said would be if I didn't spend
too much, every year would be enough.

BOB HOWARD
I've been invested in real estate and also invested in other things, in stock market. So not
always true, but everything has worked out extremely well. Well, we met and casually in
church many years ago, maybe 40 years ago, and we also both did bike rides and then
she left for New England. And when she came back was about a year after I was widowed.
And so I saw Marge at church again and didn't think too much about it. I know she was
visiting with her children. And the next week she was there again. I said, "Marge, when you
and going back to New Hampshire?" She said, "I'm not going back. I'm here to stay." I
thought, oh, about that. So set to a lunch and.

MARGE LANE
I was delighted. It was unexpected. I said, "oh, this is very interesting. An attractive man,
no stranger."

BOB HOWARD
We talked about the possibility of living together fairly early on in our relationship. Marge
was not ready for that first of all. And secondly, she felt that house was too much of my late
wife, which it was. And I told her the house was not that important to me. And so I decided
to sell it. And I bought a different conda, condominium very close to where she was. And
we continued to date and then we took a cruise together in the Baltic.

MARGE LANE
That was early and that was a courtship event. So I was comfortable in letting him pay for
that.

BOB HOWARD
I said, "all you have to do is come along." And actually, I would pay for all the trips, I don't
have a problem with it. But Marge has a problem with that, she insists on it. When, when
we got back and we decide to make that regularly. So we had dinner every night. Some
nights at Marge's place and the others at my place. We did that for a couple of years.
During that time, Marge wanted to buy a condo of her own. She was renting one. She saw
one through me that she was, she really loved it. But her financial adviser said, "you can't
possibly buy a condo at this point." I said, "you know, Marge, I can buy it. You can rent it
for me." I bought it. Marge moved.

MARGE LANE
I think you made up a lease.

BOB HOWARD
And I told her, "the only thing that I expect is if you're living there under that terms, you're
gonna pay the rent and that's it. If it doesn't work out, it doesn't work out."
MARGE LANE
I was happy with his proposal for my renting from him because there were no strings
attached.

BOB HOWARD
I figured Marge was the right person for me and I was the right person for her. And that if
this is the way she wanted to live, was OK with me and our children and our siblings were
all happy with this arrangement. So about a year ago, I knew that I was going to have a
mitral valve repaired. Everything went fine. So afterwards, Marge had brought some
champagne to, to celebrate. And I thought, well, I wonder if I ask her to marry me, what is
she gonna say? Am I gonna ruin a perfectly good relationship that we have? But I said,
"oh, what the hell."

MARGE LANE
It was, it was sort of. It was lovely. And I, I said, "yes." And I think if at first I wasn't quite
sure whether that's, that was the question.

BOB HOWARD
I asked for a prenup because my lawyer said that you had to be in, some changes in
Virginia law.

MARGE LANE
I thought it was a good idea. The only issue was it took the lawyers a long time to put the
papers together and then writing the checks for the legal fees. But I'm glad. And I think
Bob is that, that that we did it.

BOB HOWARD
Early on, she said, "you know, Bob," she said, "I'm a very independent person." And I said,
"you know? That's not a problem with me. I expect somebody to be independent."

MARGE LANE
I wasn't as needing the formal ceremony and I was happy with just a, a commitment
relationship. But the more I thought about it and the more he felt strongly about it, I thought
to myself, well, why not? If you're going to be committed, why don't you be committed to
the whole thing? Not just half of it.

BOB HOWARD
We were planning to continue to live the way we were with our separate places. But in the
middle of the winter, we said, "why are we doing this?" You know, so as a result, I bought
another one that we now live in.

MARGE LANE
It's worked out comfortably. He's always shopped at Harris Teeter and he likes bargains.
He's a man comfortable financially who likes to get, get the sales. And so he goes on
Thursdays when they have the senior discount and they have all kinds of good deals.

BOB HOWARD
And so she's insist on paying her share. But really what she does, she pays me the same
amount every month. And it's a little bit more than what you pay, paying me for rent, than
the other place. So I told her, "it's more than she needs to pay." But she insists. So I let her
insist.
MARGE LANE
I married a man of substance. And I'm very fortunate. It's not the only reason. But it was
part of part of his appeal. All of the things that I would have gone for when I was 50, five
years after my divorce, I didn't know who I was looking for. But I had, you know, ideas
about a poet in hiking boots. And Bob is neither. But, but if he had, had asked me, I would
have rethought that, those requirements around it.

LAURA STASSI
The reason I love Bob and Marge's story is because they were both willing to compromise
and they both got what they wanted. Marge wants to keep their finances separate. She
actually pays her share of the living expenses to Bob every month. And even though Bob
insists she doesn't have to, he goes with it because that's what Marge wants. They've
merged their lives without blending their finances and they're happy. In April, they'll
celebrate their one year wedding anniversary.

So here's what I've learned. I probably have some outdated notions when it comes to
money and dating and I should rethink them. While I'm at it, I should probably take a closer
look at my own financial picture before I think about having any money talk with somebody
else.

Dating While Gray is produced by Poncie Rutsch, Patrick Fort, Ruth Tam, Julia Karron
and me, Laura Stassi. Our theme music is by Daniel Peterschmidt and Mike Kidd mixes
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Thanks for listening. We'll be back next week with more stories of Dating While Gray.