This is Dating While Gray: the grown-up’s guide to love, sex and relationships. I’m Laura Stassi. If you’re like me, you’d rather talk about anything but your bank account. Stick with me, we’re gonna face it together on this episode of Romance and Money.

When it comes to older people and money, here are two facts. Number one, time is not on our side. We have more earning years behind us than ahead of us. And there’s less time for any invested dollars to grow. Number two, some of us, especially if we’re uncoupled, are worth less than we used to be. Maybe we lost a job and couldn’t find another one that pays as well. Or we got overwhelmed with medical bills for a dying spouse. Maybe we got divorced and divided it all up. And unless we’re like Jeff Bezos, who split a multi billion dollar pot in his gray divorce, we’re feeling pinched.

So I think it’s understandable that a lot of gray daters are uncomfortable talking with potential partners about money, we may feel uneasy about our personal financial picture. What details should you reveal about what you have? What you want what you need? We worry, we’ll be judged. I know I judge. I roll my eyes, If ever a date tells me about all the money he had to pay to the ex wife who stayed home to raise their kids. Does he seriously believe that has no value, not to mention, enabling him to focus on his career? Maybe I’m not being completely fair, he really could have gotten a bad deal. And now he wants to make sure women are not interested in him only for his money. In fact, some of us have been so financially burned, that we literally can’t afford to be vulnerable. It’s a lot to think about. So I’ve asked for help from someone who usually looks at money from an uncoupling point of view.

SHAWN LEAMON

My name is Shawn Leamon. I am a certified divorce financial analyst.

LAURA STASSI 

To be honest, I didn’t even know such a job existed. Shawn uses his expertise in tax laws, asset distribution and financial planning to help people get equitable divorce settlements. And interesting fact, he’s also studied philosophy.

SHAWN LEAMON

One of the great things about philosophy is that you you’re forced to think about all sides of an issue the philosophy degree helps with that is why do you think this way? What’s your motivations? How did you come to these conclusions about life about money about what you want out of life?

LAURA STASSI 

Throughout this episode, Shawn will be giving us his tips on dealing with money and romance. First, though, I asked him if older people are more reluctant to question their personal beliefs about money.

SHAWN LEAMON

I think that attitude has shifted a lot 50 and 60. And, and even approaching the 70 year mark, they approach life as if they’re 22. Not saying they’re out partying in a club or anything like that every night, but they still have a lot of vigor for life. We’re in an era now where if you’re 50, you’re just getting warmed up, it’s okay to know who you are. And that’s different, right? You may have core principles, or you may have a really clear sense of self. But that doesn’t mean that you’re inflexible or set in your ways and any means. And, you know, we all still have ways that we can improve.

LAURA STASSI 

I like your use the term core principle, would you say the way you handle money or think about money is a core principle?

SHAWN LEAMON

I think so I think everyone has their views, or when we talk about philosophy is actually I think everyone should have a philosophy in terms of how they think about money. One of the things or exercises I like to go through with people is, how do you want to use your money? Do you want to have substantial savings? Do you treat money as something to acquire things like car collectors or like art? Or do you treat money as a way to buy experiences? Or do you want to treat money as a way to invest in your kids? How much debt Are you willing to put yourself in? For certain things? And for what causes or what about medical bills, there’s lots of kind of core areas even within money in terms of how you think it should be used and what’s meaningful for you. I mean, money itself is purely a tool, right? And so that tool, you get to decide or you should think about how you want to use that tool for your future or for other people’s future. Let’s just say two people are on equal financial footing. What if one person likes to spend a lot and one person likes to save. How do you navigate that element of a relationship or future new relationship from dating? And so one of the things I do all the time is I say, hey, write down your top five thoughts about how you want to use your money.

LAURA STASSI 

You know, what you said, just really struck me as you could have a very robust conversation about money as a value, how do you like to spend money? Or what’s important to you? What do you want to do with it?

SHAWN LEAMON

You know, I think there’s a lot of fears and pent up emotions and things that we all bring to the table from how we grew up to how we’ve lived, and how hard we’ve worked, right. You know, if you’ve been earning for 30 years, or 40 years, and you’re retiring, and you like, I’ve earned this, there’s so much tied up into it, but it’s okay. There’s nothing wrong with that. One thing is to know what you have, right? If you don’t know what your own plan is, I wouldn’t be worried too much about what someone else’s plan is, when you’re just venturing out find someone who’s compatible. Most have relationship time is spending time with someone not spending money. And so make sure you like that person for who they are not how many zeros are in their bank account. If you are getting serious, or you want to Don’t be afraid to have those conversations, it doesn’t have to be intimidating. It may be uncomfortable at first for about two minutes when you bring it up and say, Hey, can we chat about money in our life and our goals. But if you are planning for another 10, or five or 10 or 30 years with someone else, you’re going to have to bring it up and it doesn’t have to be hard or scary. And the more you do it, the easier it becomes

LAURA STASSI 

Talking about money. As Shawn said, it’s a necessary conversation with the right person. And it’s not a one and done kind of thing. A woman I’m calling Ginny learned that lesson the hard way. Ginny was married to her college sweetheart for 25 years. And for a long time, money wasn’t a problem.

GINNY

From the time we got married, we kind of had a division of household bills and responsibilities because his income was more. He tended to be the one that was responsible for paying rent when we were first married, and then, you know, mortgages after we were able to purchase our own home. Then several years ago, during the recession, Jenny’s husband got laid off. He landed some consulting work, but consulting can be unpredictable. Jenny wanted to make a plan to save more money to make sure they could cover their bills during the downtimes. But her husband, he’s more seize the day.

LAURA STASSI 

So when they weren’t arguing about money, they were avoiding the subject. Ginny had no idea how bad things had gotten until the early days of the pandemic.

GINNY

This was mid March, and there was a loud knock at the door. I went to go answer it. And there was no one there. But there was a summons that had been taped to the front door.

LAURA STASSI: You’re at home.

GINNY 

I’m at home …

LAURA STASSI: And there’s a summons taped to your front door.

GINNY

My first thought was Oh, they must have the wrong house. This has been for for us. But then when I pulled it off and looked at it, it was a summons for court related to our home, which had been apparently sold at auction.

LAURA STASSI 

Wait a minute. To sell a home at auction. That means the mortgage has not been paid for how long, though?

GINNY It had been six months.

LAURA STASSI: Had you seen any notices in the mail?

GINNY

No, no, I hadn’t. And you know, I, I worked pretty long hours. And my husband worked for himself and had switched to online. So he was home. So as this ruse unraveled, you know, I came to find out that no, there had been a number of notices that had come but he had intercepted them.

LAURA STASSI 

So you had no idea he was not paying the mortgage?

GINNY

None. I mean, I’m a smart, educated woman with several graduate degrees. And somehow yes, I missed this big thing.

LAURA STASSI 

And I wonder, I mean, surely he knew you’re gonna find out sooner or later. What was he thinking? It’s like, almost like a little kid. You know, hiding the broken vase or something.

GINNY

I mean, that was even a lesson we taught our children. It’s better even if you’re something that you’ve done that that you’re going to get in trouble for or, or that isn’t going to be a you know, a great idea. Let us know, before we find out because eventually those things catch up to you.

LAURA STASSI: Was he home when this summons was …

GINNY Yeah, in fact, I was the one that was pulling it and reading any cut came and tried to take it out of my hand. And I remember us stepping outside into the backyard so that the kids wouldn’t hear us.

LAURA STASSI: Oh, they were home too!

GINNY 

They were there. Yeah.

LAURA STASSI Oh my gosh.

GINNY

But I just was like what in what in the world and what it is Hey, oh, well, I was going to tell you and I haven’t been getting paid on this one contract. I remember shaking with this belief, we no longer own the house, when are we going to have to move and a pandemic?

LAURA STASSI 

And if you thought you might have had equity?

GINNY

I yes, I did, indeed. Yep.

LAURA STASSI 

If he had come to you sooner, would you have been able to resolve the issue?

GINNY

I certainly had enough in investments could have borrowed against that or, you know, taken some of that out and then come up with a plan to pay that back. I think for me, I would have set a time by which, you know, if he were not paid as he was supposed to have been for the contract work, then, yeah, that probably was a time we would need to go ahead and sell the house.

LAURA STASSI 

Do you believe that’s what happened, that he wasn’t getting paid and that’s why he wasn’t paying the mortgage? Or do you believe there was mismanagement or gambling or something else?

GINNY

That’s immediately what I thought like, are you gambling? Are you having an affair? Or, you know, do you have another family? I mean, you hear all these stories about these secrets that have been in marriage. Since we had a joint account, I was able to go back through and look at things he hadn’t been paid. But it also appeared that he was not consistently being paid for quite some time, and that this should have been a conversation that we we should have had a long time ago.

 LAURA STASSI Oh, boy.

GINNY You  know, at this point, it had been a decade of this stress. Yeah. And just instability, financial instability. I remember going for a walk and calling a girlfriend and calling my mom to actually, and just telling them, like what I had just discovered, because it It sounded so weird to even say it and enunciate it because it just seemed so implausible. Eventually, those conversations ended up turning to trust. And is it possible to regain trust? And I the ultimate answer I had was no. So no, it was shortly thereafter that I decided to start making a plan for separation.

LAURA STASSI 

Was this a joint mortgage you had on the home?

GINNY

It was so now my credit has been ruined. Now renting even to be able to do that? My mom ended up co signing for me, which was just embarrassing at 50 years old.

LAURA STASSI

And what about the kids? How did you tell them?

GINNY

So I think this is one of the things I still struggle with. The kids don’t know, the specific reason our daughter lives with me primarily, my son is angry with me that I moved out,

LAURA STASSI 

Doesn’t your husband have to move out to?

GINNY

No, he actually ended up working with his family to buy the house back, which is a whole nother therapy discussion, right. But you know what, I started working with a financial advisor. We’re setting goals for retirement, but also ultimately, for me to buy my own place. I am in the black every month, and then some because I’m in control of my money and my finances. And I just I have stability and peace of mind, which I haven’t had in 10 years.

LAURA STASSI 

Yeah. I think I would be so angry. You seem so calm.

GINNY

Lots of therapy, Laura, lots of therapy. I definitely have trust issues after all of this. And I think I have to figure out what do I want a relationship to look like? What do I want finances to look like? I am definitely gun shy about getting into another relationship.

LAURA STASSI 

They didn’t tell the kids! On the one hand, I understand wanting to shield teenagers from ugly details. However, this seems like dragging out a bad pattern of not talking about a really important topic.

SHAWN LEAMON

Look, I don’t fault anyone for those kinds of mistakes. Unfortunately, it happens every day all the time to 1000s of people. You know, the biggest thing I always say is, hey, look, it’s all right. start planting a good future and you’re going to take charge of it for the next 30 years of your life. On a broader level. It’s staying informed, check in on your financial situation, make sure everything’s in good shape, you know, check your own credit report. Look at your accounts. Once a month, we have a little bar and our kitchen, we take 10 minutes, you know, we either pour a glass of wine or make ourselves some cocktails; go over what happened for the week or for the month and then move on. But it is both people being informed.

LAURA STASSI 

I met another woman who thankfully has not had the experience of getting financially burned. She hasn’t found a partner yet. Is she overly cautious or has she set the bar too high? Or maybe her parameters are too narrow.

SUE

I had a man say to me, you don’t need a man. Well, I don’t financially need a man. Yeah, I don’t socially need a man, I would like a partner, but this person needed to be needed.

LAURA STASSI 

We’ll talk with Sue after the break.

BREAK

LAURA STASSI

Sue devoted her younger years to higher education and climbing the corporate ladder. And it paid off. She’s now in her mid 60s, retired and in great shape financially. Sue says she’d like to find the one but so far, no luck. She does have an opinion about why

SUE

I have kind of developed what I call a little theory of there’s a triangle of men and a triangle of women. And as you get higher up in the triangle, you know, more educated intellectually curious, financially stable, and so not to pat myself on the back too much. I’m somewhere in that upper area of the triangle. And as such, I would like to find a man who is similarly situated. Very often the men in that area of the triangle aren’t necessarily interested in a woman who is similarly situated, they wanted someone a little bit farther down. A lot of men want a mentee rather than an equal and intellectually curious partner.

LAURA STASSI 

Let’s talk about this triangle theory for a moment because I think it might strike people as elitist. What makes you able to be at the top? Is it based on financial worth, financial success education level? I mean, how do you discern?

SUE

Now that you say it, I’ve never thought about the fact that it sounded elitist. My grandparents were immigrants. And my grandmother worked to clean offices, and my dad was a blue collar worker. And so I just think about, you know, rising up from that initial way of life, I’m intellectually curious and educated, I own my own house. So I’m financially stable and should be comfortable in retirement, I have a season subscription to the Baltimore speaker series and to signature theater, I like to do those kinds of things. You know, so what I say is that, if meeting, somebody is going to take away something that I already have, you know, I don’t know that how much I would be interested, I want somebody to, to add and enhance what I have, rather than take something away, that I already have, you know, I don’t know that I would be prepared. While I have provided for myself financially, I don’t know that I would be prepared and want to and be willing to financially support a partner.

LAURA STASSI 

I think there are so many stereotypes, especially at this age, like I posted something on the Dating While Gray Facebook page about a man in his early 70s, who got married to a woman in her 30s. And you know, the comments for Oh, you know, he’s her purse, and she’s his nurse or a nurse. And I feel like that it’s refreshing in many ways for a woman to be saying what you’re saying, I’ve heard from men, especially divorced men who may have had financial setbacks because of their divorce. And they’re like, Look, you know, I’m just getting back on my feet. You know, I had to give my ex wife half of my retirement pay. So I’m really looking for somebody who’s financially independent, as so I do like that. It’s a woman saying this, I’ve worked hard all my life. I don’t want to compromise in any way that would make me feel uncomfortable. I’m hearing that from you. You’re saying you don’t want to compromise that you’ve worked hard to achieve what you’ve achieved? And what’s the point in giving up something?

SUE

Right, because I do have a social circle. I don’t have to have a man to do that. And I have early in my dating career in my 30s I had a man say to me, you don’t need a man. Well, I don’t financially need a man. Yeah, I don’t socially need a man. I would like a partner, an equal partner, but this person needed to be needed. He wasn’t comfortable with me because I didn’t need him in the way that he needed to be needed. I got an email from

LAURA STASSI 

A man emailed me. He thinks fnancial independence might be code for No, I want that you make a lot of money.

SUE

So yeah, when I say financially independent, I don’t mean a lot of money. I just mean, somebody who has sufficient resources to support the life that they would like to live by. I’m not extremely rich, and I’m not looking for somebody who’s extremely rich. But again, going into retirement and to your perceived age of demise. You know, I have longevity in my family. I have one grandmother, who was 99, another one who was 93, my dad was 87, I have looked forward to be able to support myself into the 90s.

LAURA STASSI 

Somebody hearing this might think, okay, she must have been burned in the past, you know, maybe she has trust issues. How would you respond to something like that?

SUE

I have had some good relationships. And yes, there are a few where I’ve been burned where I thought that I was in a monogamous relationship. But, you know, am I so burned and damaged that I couldn’t move forward? I don’t think so. You have to have the same values? How is it that you ended up in debt? Is it because you, you took too many trips, or you bought, you know, expensive watches and things? Well, I’m sorry, that’s that’s a non starter, because that’s not the way I live, I live within my means. And certainly, I’m not going to be willing to bail someone out who frittered their, their money away?

LAURA STASSI 

What if they didn’t want you to bail them out? You know, let this guy just charge up the trip to Australia on his own credit card, because it’s not affecting you.

SUE

I don’t think I would be comfortable with that. Because if it does affect him, despite any kind of legal agreement, it would affect me emotionally watching someone, you know, put themselves into debt. Again, I think the key is to have the same values. And if you do, they’re not going to end up like that. So yeah, if they don’t have similar financial values, I don’t, I think that would be a non starter.

LAURA STASSI 

Think Sue might be making certain assumptions. Maybe these notions are preventing Sue from considering a wider range of romantic options.

SHAWN LEAMON

Only dating people who are in your tax bracket, so to speak, you can I mean, everyone has their I don’t have any judgments. Either way, if you’re dating someone, and they start asking for a loan, or they say, Hey, can you pay for my kids X, Y, or Z, that’s when the red flags start coming up in terms of if that person is in it for the right reasons, but I have plenty of people I’ve consulted with as well as some very close friends of mine, who have dated people or who are currently married to remarried to people who are not an earner, or didn’t earn nearly as much as they have, and they had the the conversations and all is fine. It’s just really being clear and open with that person as to what you want what you need. And if you have concerns, definitely being sure that you’re protecting yourself and maybe not opening up a joint account with that person after two months.

LAURA STASSI 

You know, I’ve met people without college degrees, who’ve had very high income careers. And I’ve met people with college degrees who haven’t. And that brings me to Barry. Like Sue, he’s in his mid 60s and he’s retired. He enjoys going to concerts and plays, and he’s into fitness. And he’s totally debt free. Like he outright owns his small condo and his car. But Barry thinks is relatively modest lifestyle has had a negative impact on his romantic life.

BARRY

It’s an odd thing. I have always been right at the median income level. And of course, the meeting in person has a love life. But at the same time, the two experiences that made me concern there were financial issues involved in how I was being evaluated as a romantic partner were pretty strong.

LAURA STASSI

Can you tell me about them?

BARRY

The last few years, I would get first date after first date after first date, and nothing beyond that. So finally, I had a first date where it just went great. They will none of those awkward lows in the conversation. We were really good rhythm. And at the end of the evening when I’m brought her home and I leaned in for kind of what I thought would be a very light peck on her lips. She just grabbed me and gave me this impassioned goodnight kiss that just left me feeling like my god, you know, she really likes me. So when she turned me down for a second date, I said Look, I need your help with something I said I will never get to see each other again. I’m going to break all the rules of dating etiquette. I said this has happened to me again and again and again. I know you had a good time last week. And that’s when she said, I’ve been very successful in my career. I’m not going to get involved with a man and risk compromising my lifestyle, her exact words with a man who you know, who’s who’s who’s a social worker and drives, you know, an all subcompact car. And she even she went on to say she had suggestions for me. She said, You bought that car new, didn’t you? I said he I new cars, I pay cash for them. I don’t have any debts. And I don’t have to worry about maintenance expenses. She said, Yeah, but you could trade that current and take out a loan and buy a used of that. And you could sort of finagle the way you describe your job to make it sound a bit higher level. And I said thank you when hung up, but I thought this is a very, very shallow woman. That’s what that’s just crap.

 LAURA STASSI 

That’s my first thought. The woman who told you that you needed to be splashy, or basically was she your age

BARRY

Oh, yeah, she was a sales rep for I think, I think some kind of food company.

LAURA STASSI 

Okay. Okay. But you didn’t know whether it sounds like maybe she made good income, but you don’t know if she was in debt or anything like that. You didn’t know her, the details of her financial life?

BARRY

No. And that actually is one of the things about my financial status. Although I make a social workers salary, I’m really good with money. I have no debts, I pay cash for everything. I’ve invested. Well, I can honestly say I have no financial worries at all. I don’t know anybody who can say that. So I don’t make much money. I’ve done well, with what I’ve got

LAURA STASSI 

Living within your means and saving for retirement. It sounds like that’s what you did. You know, on behalf of women everywhere. I say I’m very sorry. I didn’t think things like this happened.

BARRY

Okay, but but you know, I went to your podcast hoping to find women in this age group who would say things like, you know, now that I’m a tour, I know just how important is to have a deep emotional connection with a man and I met this guy who was so easy to talk to. Now we’re in an exclusive relationship, but that’s not what I saw at all. Okay, tell me what you saw. There was the one who said she dated a guy for a while it became exclusive. I’m not sure if they were married this exclusive. But somehow it came up that she had been renting it couldn’t afford to buy a condo, so he bought her one. There was the woman who she met a guy, it was like a first lunch date. And the better turns like a six hour long discussion, after which he and I will show the next line was going to be so he took me out to dinner that same night or he, you know, he asked me out for another day, but instead it was he invited me to spend the weekend at his beach house.

LAURA STASSI 

Okay, um, that for just a second. Because, okay, the woman who he bought her condo, he bought a condo, but it was a kind of a business arrangement. They had been dating for a while, she insisted on paying him rent. And then the woman who they had a six hour lunch, and then he invited her for the beach. They had been set up by a matchmaker. I don’t think it was the fact that he was inviting her to the beach house. And she was excited because that meant he had money. It meant like, Oh my gosh, he’s already invited me to go away with him. So I’m wondering if maybe, and I’m playing devil’s advocate here. Maybe this one experience with this one woman coupled with the car, and the younger women flirting with you because you had this cool car? Maybe this is causing you to see everything within the prism of financial status. What do you think?

BARRY

Well, yeah, that’s that is certainly a possibility. But it was it was striking, looking through the podcast, the men that those women are associating with all of them are many, many stages higher up on the income ladder than I am. You have to wonder, I have to wonder at least, how would they feel about a guy who showed up in a five year old car and was content being a social worker.

LAURA STASSI 

But I would also say if women are avoiding you because they don’t see you as a source of income, that’s a good thing, right? If there was someone who was recently divorced and might have a little credit card debt, because she’s putting two kids through college, would you be willing to meet them?

BARRY

I mean, if they were looking for someone help them pay off credit card debt, that would be a red flag. If they were looking for a guy that could who maybe take them out to a show and help them forget about the stress of having two kids in college and credit card debt. –I’d be fine with that.

LAURA STASSI 

I mean, I’d like to think it’s possible that it that it was something else,

BARRY

maybe it’s not money, and that’s great, but then where does that leave me?

LAURA STASSI 

Where does that leave Barry? Well, I think he just needs a little help selling himself, so to speak, because his financial situation is a positive quality. I mean, debt free. Why would anyone go thumbs down on that?

SHAWN LEAMON

Yeah, one of my very best male friends is in that same category. I mean, he He’s in his mid 50s. And you know, his wife was the primary earner. And he’s now ex wife, I should say. And you know, he has his same doubts all the time, money is just one piece of things, right. And if someone turns you away, because you don’t have enough money, I always say it’s a good sign.

This person is a social worker has done a great job. I mean, he’s saved up, he’s been financially set, it’s better than, to me at least, if I were him, I’d be like, gosh, you’re in better shape than 98% of Americans out there, because you’re not trapped in that you’re not trying to run on this treadmill, where every month you’re trying to keep up with all your payments and live some crazy lifestyle that you really can’t afford. I know from seeing a lot of people’s financials, there are a lot of people who live exceptional lifestyles from the outside who barely make it every month to cover their bills.

LAURA STASSI 

Shawn says you don’t need to be wealthy to benefit from the services of someone like him. And to learn more, you can go to his website, divorceandyourmoney.com. You know, Sue mentioned values, but I had the lightbulb moment when I talked with Shawn. Money is a tool and how we use that tool. Like Shawn said, that’s a core value. So by thinking of it that way, I’m hoping it’ll be easier when it’s time to bring up the money topic with a potential partner. I haven’t done it yet. It might be because I haven’t met the one. But it’s also just as likely because I’m still uncomfortable talking about money. I mean, if I were forced to choose between, I don’t know letting someone look at my bank account or letting them confirm the color of my underwear….I don’t know. Hold on, I’m thinking, I’m thinking!  Seriously though, if recoupling means getting comfortable with money talk, I’m willing to change

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