EPISODE 5: What (Some) Men Want

Published 11/02/23

This is Dating While Gray. I’m Laura Stassi. And when I call this show the grown-up’s guide to love, sex and relationships, I like to think I’m including a variety of viewpoints for singles 50 and older. But there are times I realize I’m coming up short — and I’m usually over looking straight guys.

“What (Some) Men Want.” That’s next.

The last time I was online dating, I got a like from a man recalling Matthew.

I’m retired after almost 25 years in the Coast Guard and then a position with the federal government. I’m active in email loving Congress each day on veterans’ issues.

With Matthews permission, a voice actor’s reading excerpts from his online profile. Matthews divorced in his grandkids. When he sends out likes, he asks women to please read his write up before responding. He serious it’s at the top of his profile in all caps, and with two exclamation points.

I try and keep fit. I have about 10 more pounds to lose.

Matthew exercises almost every day. He likes dogs. He has a graduate degree. And he’s currently reading short stories and Italian.

Most people consider me to be a nice guy, but not afraid to speak his mind. I’m also a bit bookish, perhaps even nerdy. That is just the truth of the matter.

Matthew is forthright about who he is. He also clearly states what he’s looking for.

I need a friend and someone who’s willing to explore all avenues of a relationship, including sexuality. I’m not against the long term relationship, but I have no desire to marry again or cohabitate. At the same time, I’m not looking for a strictly platonic relationship either.

Now, I have a hard time separating love and sex. So Matthew and I would not be a good match. And apparently, a lot of women feel that way. Matthew says his likes usually go unanswered, which is okay by Matthew. He also says in his profile, “you should not respond if you are not interested. A no, thank you, is not necessary.” So why do some women respond to Matthew? Not to say no thank you, but to criticize his stated choice? To tell him that what he wants is wrong. Matthew told me that happens. And it makes me wonder, when it comes to older heterosexual dating, are women basically trying to tell men how they’re supposed to feel and act?

STEVE 02:31
One time dating coach gave the advice of, “if you can’t afford a cup of coffee, you can’t afford me.” And I thought, oh, my, you’re purchasing women. You’re telling men that they have to purchase women by, you know, buying them lunch, or buying them dinner, or whatever, or a cup of coffee.

That Steve, a retired professor and widower in Wisconsin. Steve says he feels like some women are trying to school him — women he’s met in real life, and women he’s heard on this podcast.

STEVE 03:01
Well, it didn’t happen right away. But you know, just over the course of you know, like three years listening to your podcast, I regularly had a thought that it seemed as though the people that you had on –the dating coaches — were coming from a very gendered perspective; that they were, they were talking and giving advice to people who were the traditional masculine male, the traditional feminine female. And these prescribed roles that men and women were playing were, the men were the initiators. They had the social power in the sense of being proactive. And the woman was reactive passive. Often advice given was, don’t contact the man after the date, let him contact you. And my reaction was, what the heck is this all about? This is not my experience at all in my life, you know, dating back to my 20s when I was in college, and then in graduate school.

So I, I sort of put those to the side. But then there was an interview did with a woman from Chile, I think it was.


STEVE She was talking about how she spends her money, you know, preparing and making herself beautiful, but a man can’t do that. And so the way that he shows interest in the woman is by, you know, paying for dinner. And that’s when, okay, I’m gonna just write to you and say, there’s a whole segment of the population that you’re missing here. And that is men and women who are in their late, you know, in their 60s, 50s, 60s; went through the Civil Rights Movement and the gender rights movement of the ‘70s. And they’ve tried to throw off those gendered roles and behave equitably toward one another and not have these circumscribed gender roles that limited the both their personality and the things that they were capable of doing with another person.

l’m a little bit you older than you are. But I remember like in high school, we had the Sadie Hawkins dance. And that was the one time it was okay for a girl to express interest in a boy. So some of us are sort of breaking out of those roles. But then when it comes to dating, we are expecting … to be wooed. I don’t know how else to say it.


LAURA STASSI   And wooing doesn’t just mean money. So when you show interest in somebody, how do you –first of all, where are you finding partners to date? And then how are you expressing interest?

STEVE  05:35
I have had some of my friends set me up with women, or I show up at a dinner party, and there’s a strange woman there, you know. That actually prompted me to get onto dating sites, online dating sites, because I wanted to be proactive, I didn’t want to have my friends, you know, picking out eligible women for me.

Okay, as an eligible woman, may I say, I would love to be invited as the extra chair to dinner party. I think that’d be great.

STEVE  06:05
Well, but as the person who’s blindsided by that, then you have the potential to disappoint two people, two sets of people. That’d, be the person who is being set up, and then your friends who think they know what you want. So I mean, that happened a couple of times, and I went on those dates, and then I decided I needed to start dating myself, you know. And that’s when I went on match.com or eHarmony, or something like that.

I do hear from a lot of people who have first dates at a restaurant.

STEVE Right.

LAURA STASSI  Or, you know, dinner and drinks or even drinks at nighttime. And it feels like, on the one hand, you don’t want to appear to be overly frugal. But on the other hand, when you invest a lot of money or time in a first date, that can be fraught with some of the things you’re talking about.

STEVE 06:57
Well, I guess my feeling, right at the beginning, is that if two people are interacting online, and then one of them says, Hey, do you want to get together? If the other one says, Yes, I do, then they’re both expressing interest. We’re both expressing that we want to get together with the other person. I would assume, in most cases, that when the check does come — whether it’s just drinks or if it we, we decide, hey, let’s have dinner; this is good, let’s keep on going — that we’d split it. But again, I’m not somebody who necessarily says that when the check comes. And this is something I’ve learned just, you know, as, as I started doing this, after, you know, almost four decades of not dating. There have been times where, you know, the check sat there and a woman, the woman just sort of starts pushing the check toward me. And at that point, I just say, Okay, I guess I’m gonna pay for this. I never say to a woman, I’m only going to pay half.

Does that impact how you feel about that woman, and whether you want to go on a second date?

STEVE  08:02
I would say no, I don’t think so. You know, I think at the end of that conversation, at the end of the date, I have a pretty good idea whether I want a second date. And I would say that 80 percent  of the time that I go on a first date, there is no second date, you know, that I or the woman decides that well, okay, maybe not. But I don’t think the picking up the check, I don’t think that’s ever been the determining factor. There are other things that happened that have nothing to do necessarily with any kind of feminist beliefs that warn me off or cause me to think, ah, you know, I’m, I don’t think I want to pursue this.

I appreciate your use of the term feminist because I. personally, am on the cusp of where people were kind of embarrassed to embrace that term. I guess.

STEVE It’s still the case, I think, yeah.

LAURA STASSI  And I am a feminist. But I, a lot of times I caveat that “I’m a feminist, but …”

STEVE 09:08
what I often say is, if you’re a fish, you don’t realize you’re wet. Because wet is all you know. And when you talk about cultural upbringing, there’s a lot of things that we learn and grow up about and are socialized about, we don’t question. And it only becomes when we see an alternative point of view that we begin to question those assumptions. And then we realize we’re wet.

You wrote about “some surprises along the way that have been eye opening and humbling.”

STEVE 09:37
There’s one it was maybe my second or my third first date with a woman. And, you know, we had like a beer and, and tea or something. You know, we talked for a couple hours and afterwards, we said let’s get together. So I texted her at one point shortly afterwards. “I’m still kind of new to this and I’m, you know, still trying to figure out you know, the rules and everything else.” And her reply was something like, okay, here’s how it works. Boy asks girl out to dinner, boy pays, then this happens a couple times, then girl invites boy to her apartment makes dinner for him. And then it proceeds from there.

I said, that might be one way to do it. But I’m a feminist. And so I don’t like to sort of follow gender roles. So maybe it’ll be a little different with us. And then about two hours before the date was supposed to happen, I get a text from her saying, you know, I’ve had a long day at work, I’m really kind of tired. Maybe we can do this some other time. So I think it was the fact that I responded that way that she, you know, cut off the date,

Overall, what are you looking for?

STEVE  10:56
You know, that’s an interesting question. Because if you had asked me that maybe a year ago, I would have said, Yes, I’m looking for, you know, a long-term relationship, a committed relationship, where we’re under one roof and everything else. But one thing I’ve, I’ve realized, and been surprised at, but then in thinking about it, I shouldn’t have been surprised about it. And that is that, you know, I’ve been involved in maybe like four serious relationships over the past three years. And one theme that has come up with these women who are, you know, very independent, they have had careers of their own, it’s very important to be independent, and to not lose their identity, lose their sense of identity in a relationship.

I hadn’t really considered that before, because I never have thought about losing my identity in a romantic relationship. In general, men have a better deal in terms of romantic relationships in our culture. If it’s heterosexual males, they have a pool of potential partners who have been socialized to be attentive to another person’s feelings, and to engage in caregiving, and to turn taking. And whereas women get a raw deal more so that they are involved with a potential romantic partner who is maybe more likely to want to get as much as he can, without having to expend much and to think of himself first.

So again, these are gender differences that are group differences. And there’s a lot of individual variation. So what I’m saying is, as a feminist man, you know, there’s a pool of women out there who would like to have a relationship with a man who treats women equitably. And so I’m optimistic that I’m gonna find somebody because I think the pool is much richer for me as a man than it is for a woman who is a feminist looking for, you know, a man who is also going to be a caregiver and a turn taker and everything else,

A true partner.

STEVE  13:14
Yes, a true partner.

I love the word partner, regardless of marital status, because I think that, you know, a partnership implies that everybody’s doing what they’re supposed to be doing.

STEVE 13:26
Right. And again, you know, in saying that, there’s plenty of women and plenty of men who have traditional gender roles who are going to find a perfect fit, and it’s great, and they’re going to have a wonderful relationship. I just know for myself that that’s not the kind of relationship I want. And so I think everybody out there should identify what they want in a relationship and how they want it to be negotiated with their partner.

Sure, but at the same time, I think it would also be great if they would consider alternatives. Maybe there’s some give and take as we get older.

STEVE  14:00
We’re all capable of redefining our social reality, right?

That’s a fancy way of saying change, right?

STEVE Yeah, change.

Our thanks to WUWM, the NPR member station in Milwaukee, for facilitating the interview with Steve. And by the way, the definition of feminist is simply someone who believes women should have the same political, social and economic rights that men have.

And you heard Steve say he was optimistic that being a feminist would help him find someone. I’m happy to report, Steve’s been in an exclusive relationship for over a year now. And he says they’re at the stage where they’re trying to figure out how to fit into each other’s families. Because even when your kids welcome your partner, it’s important to understand the challenges and opportunities for growth. Amen.

Next, I’m talking with another man who has taken issue with some of the things he’s heard on this podcast.

KEVIN 15:02
I think the divorce made me extend grace, made me more empathetic. But then again, at the same time, you know, I’m listening to the Dating While Gray and one of the ladies will say, Oh, yeah, you know, we got divorced after this period of time and blah, blah, blah. And I’m like, yeah, but did you initiate?

Okay, so are you being judgy?


LAURA STASSI  That’s Kevin. We’ll hear more from him after the break.


My name is Manuela Barreto. I’m a professor of social and organizational psychology at the University of Exeter in the United Kingdom. I led a study that looked at loneliness around the world and how it differs by age, gender, and culture. We studied about 46,000 people, ages 16 to 99, and living in 237  countries, islands and territories. We found that men report slightly more loneliness than women at all ages. But the gender difference was smaller in older participants than in younger ones.

For some men, the cause of their loneliness is gray divorce,

KEVIN 16:15
I’m trying to become the type of person that will attract somebody, right? Someone who would want to be with me. But then there’s times when the loneliness is just that — I don’t want to say devastating, but it’s like, you know, I’m, I’m leaving work, and I’m walking out to the car. And I’m like, this sucks. You know.

That’s 61-year-old Kevin in the Pacific Northwest. He married his college sweetheart, and they had eight kids. When Kevin wrote to me at the end of last year, it sounded like he was still reeling from the breakup initiated by his wife.

KEVIN 16:51
I always thought that things would work out, you know what I mean? That, that we had really good times, and we have really hard times, but that, you know, we were going to, we were going to be fine. We were Christian family, we, we went to church, and we’re pretty involved. And I knew that there were hard times, sometimes I would feel bad for my kids, because I’m thinking, you know, marriage is — being married, it’s wonderful. I hope that you all get to experience this love relationship, you know. But maybe our marriage characterized, you know, something that wasn’t so fun and easygoing,

I think a lot of us have the attitude, especially if you come from conservative or a traditional family background, you think marriage is something you do for life. Unless there’s something really horrible going on, you stick with it.

KEVIN 17:47
Right. I thought divorce wasn’t an option. And I thought that you know, that we had it beat over time. Like over time, you know, we were going to be fine. I worked hard all my life to make sure that, you know, everyone’s needs were met and some good things you could plan for. And we planned for some good things. And I just thought that the things that my wife was unhappy about would all work out.


So did she talk to you about what she was unhappy about?

KEVIN 18:16
Oh, yeah, no, no, totally. She was in counseling. And then we went, we did some counseling together. I just want to say she was just profoundly unhappy. One of the good things that has come out of the divorce is that, you know, I’m seeing things more from her perspective, right? Now that I’m outside of the outside of the marriage. It’s like, oh, yeah, that’s what she would say about me. I found this, this card that I sent her and it said, I wish you could be me, because then you’d know how much I love you. Something to that effect, right? Back in the day.

And after we got divorced, I would hear, you know, from the woman’s perspective, how they were thinking, and I’m like, yeah, I wish you were me. Because then you would know that that’s, that wasn’t my intent, or, you know, if I knew that, maybe I would have done better. But that’s kind of the turning point, right? When you no longer get the benefit of the doubt, right? When you start feeling like people are doing things on purpose, because you’re taking it personally, right.

I think a lot of people, men and women, don’t want to talk about what they’re unhappy about. And a lot of times, it’s we don’t know what we’re unhappy about. We might tend to blame our partner, which may be it’s just — you described her as profoundly unhappy. And my first thought is, was it the situation she found herself in and not necessarily feeling profoundly unhappy with you, but you happen to be her husband? Do you know what I mean?

KEVIN 19:56
I’ve thought about maybe if I would have done everything right, if I would have done everything right, if I would have, you know, met all those, and I wouldn’t even say meeting needs, but doing the things that she wanted done. I mean, it still may have not worked out, you know. She still could have been unhappy, it just would have landed on somebody else, I guess. I want to think that she’s happy now. What ended up happening is, I would be defensive.

When you’re defensive, you’re, you’re telling the other person, they’re wrong, right? And so if you’re telling someone that they’re wrong over 20 years, that’s a beatdown. I feel like that’s how she felt, that I was just beating her down when, you know, if she could be me, she would see that I was just trying to defend myself. You have to feel it with them and see if you can feel through it, you know? And again, you know, stuff that I regret, and trying not to be defensive. It’s pretty sad being as defensive. You know, I felt like that was a quality that, you know, over 20 years or so, being constantly defending yourself, you know, shields up and in, give me examples, and why that example didn’t apply. It was terrible. It was just, it’s terrible to think about, it’s just a really bad way to interact with somebody.

Yeah, well, at the same time, you’re now talking about it as though it was in the past. So that’s really good. That’s progress.

KEVIN 21:27
Well, the scary thing is that, is it? If I did come into another relationship, what’s going to stop me from doing exactly the same thing? You know, it’s like a, it’s like a habit or a personality trait, you know, and so, so there’s a certain amount of fear there on my part, you know, even though I’m trying to be the type of person that someone would want to be with. It’s on my whiteboard, and I read it regularly. But then when push comes to shove, you know, you fall back into what you’re comfortable with.

Believe me, we have all been in your shoes.


LAURA STASSI  And we’ve all been in your wife shoes. I have been accused of being defensive. And my thing is, well, you’re attacking me. Do you want me to just lay down?

KEVIN 22:15
Yeah, yeah, that’s, that’s what I wouldn’t do. You know, I figure being a man is, you don’t lay down. That’s part of being a man.

Sure. Okay. But this is interesting because you described yourself as a fundamental Christian.


LAURA STASSI  And you talked about being a man and so, I guess, very defined roles about men and women and what a marriage should look like. There was a line that kind of struck me in your original email, and I don’t know if you meant to sound like this, or if you still feel this way. But it was something like she stopped – she wanted to not go to church anymore. And you let her stop going.

KEVIN 22:55
Oh, yeah, no, for sure. I’m not demanding. She actually said to me, you know, thank you for letting me not go to church or something to that effect, you know, for letting me. And I’m like, no, I don’t think you understand, you know. I want you at church, you know.  I want you to come, but I’m not gonna force you to go to church.

To me, it seems like one of those moments where it could have been a conversation. Like, of course you’re not going to force her to go, but why is that even part of the equation? Do you know what I’m saying? Why can’t she decide on her own? I assume she’s not getting anything out of it anymore.

KEVIN Right.

LAURA STASSI  And to me, that would have been a point of if it’s that important to you that she goes. This is a foundational disagreement, in many cases. So it sounds like you had a traditional marriage where she stayed home, you worked, had all these kids, But it also sounds like your divorce was a traditional divorce.

I’m going to quote from your email, if you don’t mind. You said something like, it left you with “a hefty alimony payment, which haunts me to this day, it’s like picking at a scab, opening a wound with some months easier than others,” and that she doesn’t have to work for the rest of her life.

KEVIN 24:13
So we went into arbitration and there was a custody thing going on. And to me the money aspect was less important than the custody aspect, right? And so she did — I think she did really well. You know, in regards to getting she got all my retirement savings and half of my pension, and then the alimony and half of the house and all that. I shouldn’t say half the house because you know, you do an appraisal and they base the buying her out on that appraisal or whatever. But anyway, the way it worked out is, and the reason why I say that, every month they take out the alimony payment and it’s a hefty check. Okay, I have my paycheck, you know, and it’s like, ouch. But you know, that’s just complaining, right? That’s just, that’s just me. I don’t want to say feeling sorry for myself, but kind of just feeling sorry for myself. Because I, you know, I’m rich in so many ways, right? I’m just, I’m fine.

You had a wife who stayed home, you had all these kids; you wanted to stay married;she didn’t want to stay married. You felt like you were penalized financially even though she did stay home and raise eight kids.

KEVIN 25:30
Okay, okay. What — yes. When I’m clothed, and in my right mind, when everything is, is when I’m, when I’m okay. You know, she earned this. She literally —  you know, the workman is worthy of her wages. Right? And she’s getting her wages, she worked really hard. And this is her retirement, so to speak. And that’s fair and reasonable. And so the scam thing is me being me being stupid,

It can still hurt.

KEVIN Nah, I mean it’s irritating. Nah.

I feel like I’m just right in the middle of the bell curve, you know, just one day at a time, you know, just get through one day at a time, and then do something that moves the mark, that then moves you towards where you need to go. And my hope is, in our conversation here, that that I’ll be one of those guys that you ping back. You’ll come back and say, so what’s what’s going on now? And I’ll have some kind of happy ending.


KEVIN  But you know what? Happy ending is being everything that you can be, being the best you can be.
For Kevin, being the best you can be means continuing to keep an eye out for his kids well-being while working on his emotional, physical, and spiritual health. It also means tackling projects like decluttering, the family home, which he got in the split.

So now you’ve heard some viewpoints that have been missing from previous episodes. I’d love to hear what you think, and also what you’ve experienced out there on the dating market. Whether you’re a man or a woman, seeking an opposite sex or same sex partner, for a little while, or maybe forever. The one thing I’ve learned is there’s no one way to go about it.

Dating While Gray’s audio production and mix is by Steve Lack: Audio. For more on the show, check out datingwhilegray.com. That’s where you can find the latest episodes, plus the archive of previous episodes. You can also find links to send me questions, comments, tips and true stories through email and voicemail. You know I love hearing from you. While you’re there, sign up for the free Dating While Gray e-newsletter, delivered every Friday to your inbox. That’s datingwhilegray.com. Laura Stassi. Thanks for listening.