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Episode Transcript: Great Expectations

ROB: 00:03
I look at and say there's a 33 percent chance that I'm going to last forever in my second marriage. It's hard to imagine women who don't want to marry for the rest of their life.

They often point out like, older men marry more than older women. I'm like, so women don't want to do that. And a lot of older women don't even want to live with a romantic partner. I don't. I don't! I make that very clear to anyone if I'm starting to date. I'm like, we're not living together.

TIM: A friend of mine says you have to kiss a few frogs. And I said, none of them were frogs, they were all great. I would have to say that, you know, the first lady that I went out with, I think that she just wanted to have fun with a nice guy, and I injected a bit more seriousness into the thing then we could stand.

This is “Dating While Gray: The Grown-Up’s Guide to Love, Sex, and Relationships.” I'm Laura Stassi. And no matter what the research says or what advice we get, when it comes to new romance, I think it's hard not to have “Great Expectations.”

When a relationship ends, some people need time to get comfortable with being on their own before they can even think about dating. And then there are people like Rob.

ROB: When I realized I was going to be single again -- for what I call my second singlehood, I went down my list of all my friends, and found out seven of them had been divorced, never really thought about it. And I just scheduled lunch with all seven individually, and said, “Tell me what I need to know.”

And so at that point, what I learned that -- I'm distilling it down – that the earliest any of them had remarried was two years, and the longest was about five. And there was a suspicion that if they weren't married within five, they might be having too much fun to ever marry. Now, maybe some will, but out of my database of seven, yeah, what I came to realize was the odds are really high that if I was intentional about wanting to get remarried, it would probably happen in a two- to five-year window.

LAURA: Rob – it’s not his real name – is an entrepreneur, and he didn't get married until he was in his late 30s.

ROB: The intent was to be married for the rest of my life. And we both made that working assumption going in. We went ahead and had children, and we raised two boys for 21 years. And as we got two years out from being empty nesters, we just started doing a practical look at our lives and said okay, we've got now 30 years coming up -- or more ,depending on how long we live -- to spend with the second phase of our life.

LAURA: Yeah.

ROB: And so when you do a pragmatic view of it like that, it's just -- it sounds objective, it sounds cold, but it's really not. It's a really smart way, in my mind, to have a happy rest of your life for both parties.

LAURA: Rob took a kind of statistician approach to uncoupling; nothing wrong with that. He's doing the same with finding new love. And in the process, he's gathering some dating data points.

ROB: I have not gone out looking for anyone. I've had eight different women contact me and said, “You're single, and I have a friend.” And I've agreed happily to go out with these eight different women who all come from backgrounds not dissimilar from mine, because they're from friends of mine. So I just want everyone understand that. I'm this odd anomaly. But now I have eight data points on dating.

LAURA: Yeah, so you have never been online -- or have you?

ROB: Just a week ago, I got COVID and had five days of quarantine. It was bored out of my mind and decided to go online at the suggestion of one of my women advisor friends who's single and has been on online dating.

LAURA: Okay, so you said women advisor friends. So let's talk about this project.

ROB: It didn't dawn on me when I moved into this condo, I had to rebuild my entire friendship network. Yeah, well, it turned out moving into a condo, there were 123 units around there. And by coincidence, several of them had single women. You know, one who was older than me whose husband had passed away two years before, one who was my age who had been divorced two years before. And so we became just friends, complete friends. And I had a joke. That's true. I will not date in the building. And so that made it for a very comfortable relationship.

LAURA: Only friendships in the building.

ROB: Well, the thesis I have -- and this gets back into being practical. The only way dating somebody in your building works out well is if you marry them. If you quit seeing each other while you're still in the building it -- there's just nothing good about that.

LAURA: I can imagine. That makes perfect sense to me.

ROB: Yes.

LAURA: Okay, so, okay, so you were dating and you came up with an idea.

ROB: So it came from going out with a woman several times. And after about the fourth time, I realized all the various things she had said to me about what she was looking for in the right person to spend the rest of her life with. And so I gave great thought to that and went home after the fourth date, opened a spreadsheet, and wrote down the variables I could remember her mentioning. And there were 40.

LAURA: So wait a minute. This is interesting to me because it sounds like you went out with her a few times, no? But this was, was this a recurring conversation or was she thinking -- I mean, it sounds like, okay, was she not interested in you as a long-term partner, and that's why she kept talking about what she was looking for?

ROB: So let's assume I'm kind of good at asking questions and so on. It comes from my background in consulting. And she was happy to talk and in the course of that, she was talking about her background and her first marriage and people she dated in the meantime. And it was just part of the natural flow of the conversation further to say, “Oh, you know, my ex was this, and I'd like to have that in the future. And my other ex was not that, and I’d like to have that in the future.” And you know, if you think about your personal self, and you think, what are my variables for getting married? Most people think, oh, three, and if they think really hard, it might be five.

LAURA: Right.

ROB: And I sat there and came up with 40, that I had heard her say, is what -- that's what kicked it off. And in the course of it, by the way, I figured out I wasn't the one. So once we did that, the next time we got together, I said, “I'm going to do a little fun thing, I hope you'll enjoy it too.” And I went down this list of 40 variables, and she agreed that 38 of them really did make sense; said two really weren't that important, and then added a few more. And so at that point, I said, “Look, you can't have that many variables in life, you've got to narrow it to the top 10.” So then she narrowed to the top 10 that really mattered. And then again -- this is a little science-y, but there's something called a weighted index. So I said, “Here's what to do. I'm gonna give you 100 marbles and spread them over the 10 different things you're looking for. But do it by how important they are.”

LAURA: Like, did you actually, physically give her 100 marbles?

ROB: I didn't have to do that.

LAURA: Okay.

ROB: It was a, it was a mental exercise, imagining all these marbles going all over the place.

LAURA: Okay.

ROB: But it is an interesting exercise. Because when you sort of generally think of all these variables loosely in your mind, it's very different than narrowing it to 10. And then saying, well, whatever number one is, is it worth 20 points, or 25, or five, or 10? And so what it comes out to is, it's just -- it rank orders the 10. So one of them might be a 20, and the bottom one might be a two, but it now helps you do the analysis of what really does matter to me in the long run.

LAURA: How can you jigger your game so that men can get something out of it too -- or can you?

ROB: So to answer that question, this is a story that is not backed by data. But the more women I talked to about men looking at this, or men talking about this, men are much simpler beasts.


ROB: And this is not fair to the men listening, or anyone else. But the joke is, if you put out 40 variables, instead pick from these and they're pre-populated, you can put others they would go hot, hot, short skirt, hot. Now that's a joke. But men are much simpler.

LAURA: Well, they they're much more visually, they're visually oriented. I don't know how to say it. But I didn't want to believe it, either. But Helen Fisher, the noted anthropologist, says it. They are just, they're visual. And so based on that, they want to see a picture and if you look like somebody they want to get to know, it almost doesn't matter where you live, or if you're logical as opposed to passionate or, I don't know. But what are you looking for?

ROB: Number one, to grow old with somebody who loves me, and I love them. That's as simple as it gets. And then people who just share history with me, you know, who have a similar background and interest.

LAURA: Right.

ROB: And so I'm somebody who's a conversationalist. Somebody who's not, wouldn't be a good fit for me or for them, you know. And I have my particulars like, I happen to like cooking. I happen to be comfortable going out, somebody, you know, there's almost no one that I could date that wouldn't like one or both of those. I'm athletic and want to do stuff like hiking and so on. So they're fairly straightforward variables. It's just when I think about the things I enjoy doing, it would be fun to be with somebody like that.

LAURA: 09:28

I can't divulge any details, but Rob's working on a business venture to leverage the data he's collected about romantic partner wish lists. Sounds interesting to me, though I have to say, I can't wrap my head around 40 attributes. Seems like at some point, that is way too detailed.

So here's a fun fact from the U.S. Census Bureau. Of all the people ages 50 to 84 who have never been married, the majority are men – 51 percent, compared to 49 percent women. Kind of surprising, huh? But when counting all the unmarried people -- so the never marrieds as well as widowed and divorced -- women far outnumber men, something like 61 percent to 39 percent. And the ratio grows even more lopsided as we age. Of all the widowed, divorced, and never married people 75 and older, only 27 percent are men. So does this mean anything? We'll talk about it with an author whose book uncovers another surprising statistic or two. That’s after the break.


LAURA: Vicki Larson is in her 60s and has been married and divorced twice. She's a newspaper journalist and author in the San Francisco Bay Area, and her latest book is called “Not Too Old for That: How Women Are Changing the Story of Aging.”

VICKI: Well, you know, this wasn't the book that I wanted to write, actually, I wanted to write a book about how to age alone, even if you don't want to, because I'm a single woman, I live alone and I have lived alone for 17 years. I want to live alone, even though I'd like romantic partner. And, you know, it was kind of wondering how to really make that happen in a happy, healthy way. And even though there are many, many of my friends are partnered, the average age of widowhood in America is 59. And COVID is even pushing the dial earlier because it's affecting men more than women. So women overwhelmingly are alone as they age.

And no one wanted to buy that book, Laura, I don't understand why. But while I was researching that book and thinking about it, I just started to think about all the narratives about older women. And, and, you know, and I'm 65. And I didn't feel any of that stuff. And then I thought, well, wait a minute. Like, who's saying all that stuff, and why are they saying it? And who's benefiting from saying it and who's been hurt by saying it? And that's how this book came to be.

LAURA: Age is a funny thing, I think, in that -- and I don't think you quote-unquote, look 65. But I think it's gotten to the point where we really don't know what age looks like, if you know what I mean.

VICKI: I joke that, you know, when I was writing the book that there are no, you know, women in the Bay Area who look old -- whatever old looks like, I don't know.

LAURA: Yeah. And that shocks me – 59 is the average age of being widowed?

VICKI: Yeah, yeah. Well, we tend to marry or partner with men who are older than we are. And that's kind of like what happens.

LAURA: Yeah.

VICKI: And in many ways, I mean, I feel like we're just getting started when we’re that age. We are -- I mean, a woman at age 59 has got 20, 30, maybe even more years ahead of her. Margaret Mead called it the postmenopausal zest. That's a long time to possibly be alone, or to go and look for a new partner, if that's what you want.

LAURA: I know, looking at the statistics, that there are more women than men and as we get older, it becomes more lopsided. But your point was by, I think, 2030, there would be more older -- tell me about that one.

VICKI: So yeah, by 2030, there's going to be more people 65 and older than younger, for the first time in history. And because women live longer than men, there are going to be a lot more older women. So the future truly will be female. That's going to change a lot of things, or at least it should. I mean, we don't have the caregiving capacity for that. Because women overwhelmingly live in poverty as they age, we're going to have a lot of poor women. Because we tend to develop disabilities -- maybe permanent or maybe temporary; maybe just one, maybe several -- you're going to have a lot more disabled people. And we are not prepared for that at all. And it's not that far away.

LAURA: Why do you think -- two questions: What do you want men to get from your book about older women? What do you want older men to get from it, and why isn’t there any messages for men about these kinds of topics?

VICKI: So the way we talk about men is that they age gracefully, I guess, or they’re silver foxes or something. And a gray-haired woman is never called the silver fox. She's, you know, grandma or something like that. So there's sexism and so I think if a man is reading my book -- and I hope that men do -- they might realize whatever negative beliefs they've had about older women, they might see us in a different way. I hope. I mean, look, for some older men who like to date younger or marry younger, and I'm fine with that. He's not my guy. I like men who want women around my age. You're not going to really, maybe change those guys’ minds about older women.

But you know, I would hope that men would read it and maybe realize their internalized ageist and sexist beliefs and how they have spoken about older women. And the thing is, they all have older women that they've loved, whether it was a grandmother or an aunt or a mother -- might be touchy with Mom. But I mean, you know, they have older women that they love. And so they've seen these wonderful older women they care about, and then why wouldn't you want to be with one, you know? So yeah, I hope that men would get that from the book.

I'll just tell you a funny story that is not in the book. So I was out on a date with a guy who was in his

mid- to late 50s. This is a few years ago, so he was about five or six years younger than I was at the time. And he said, “You know, there's something going on with the women in your town.” And I was like, “Oh, really?” He said, “Yeah. You know, my friends and I, we've gone out on a number of dates with them, and they really just want hookups. They do not want a boyfriend.” I was like, “Really?” And inside, I'm thinking, “Go girls in my town!”

LAURA: Yeah.

VICKI: They were younger women, Gen X women, who are out of a marriage recently, and they've got kids at home. And the last thing they want to do is get back into that arrangement. And these guys were all like, wanting to settle down. And they're like, yeah, okay, not in this town. It's not happening. And I found that that was really interesting. You know, there is research that men start to get a little bit more bonding, like they become more woman-like, I guess -- which is a stupid thing to say. But they become more like what women are always told that we are, as they age. And women start becoming like, more outlandish and bolder and more -- we're finally comfortable in our own skin, generally. And we act like that.

LAURA: Okay, so what about, if you don't mind me asking, where are you in your life, personally and professionally?

VICKI: Well, personally, I just dumped someone.


VICKI: We hadn't been going out for -- we really, we had like six dates or seven dates over two months. I just could see that it wasn't going to be a good fit. And I'm trying, Laura, out there back on the apps and this and that. I do like someone, I do, but doesn't seem to be happening.

LAURA: But oh, I was gonna say, is it too early to talk about it? Or is it like …

VICKI: No, I can't talk about it.

LAURA: Sounds intriguing, doesn't it? As for Vicki's professional life, she found a publisher for the book she originally wanted to write. It's a how-to guide for living apart together. Vicki is adamant that she won't share space with a romantic partner 24/7. But I can't help but think, never say never. Because sometimes, expectations clash with reality.

TIM: I'm Tim, I'm 58 years old, and I've been listening to “Dating While Gray” for a while.

LAURA: Have you been dating while gray for a while?

TIM: Well, yeah, I suppose I have. Um, let's see, I got divorced back in -- well, I separated and then divorced back in 2016. And so I've had a bit of a journey through dating since then.

LAURA: Tim lives in Washington, D.C. He had a long career in the military and now works for a government agency. Tim sent me an email during Season 3, because he was finding single life puzzling. I followed up with him to hear more.

TIM: When I first separated, at first, I thought I wasn't going to date at all for a bit. But one thing I said was, I'm just not getting married again, I'm just going to have fun now. But then when I started dating, just a few months after I separated, it was like, I was looking for wife number two immediately. So I said one thing, but my actions really were quite different. And I went through a series of serious monogamous relationships with some really great ladies. And I think that I was still thinking in terms of having a permanent relationship the same way that I did when I when I got married. And so I didn't really have a good model for what dating would be like -- in my 50s, at that time, in my early 50s, without the concept of having children or any of that. So I've had to learn a lot.

LAURA: And is it just because of tradition, you know, family upbringing that you thought this has to be a serious? You know, this has to lead to something, official-commitment wise?

TIM: Yeah, I think that -- I don't know if it's family tradition, or anything. But I guess I'm just wired in such a way that the intimate relationships, especially if there's sex involved, somehow translate into a serious, permanent relationship. I've had friends tell me, “It would be great if you could get rid of that idea.” But I just -- never been able to shake it. And, honestly, it still feels like that works for me.

LAURA: Sure. And how did you find these women? Did you go online, or were you introduced by friends or …

TIM: Some of it was mutual interest or being introduced by friends. I've had that happen. I didn't go online. And I have thought about going online in the past. But there's just something about it.

LAURA: Yeah, I hear that. So I'm just interested, you know, not to be -- what's the word -- sexist or visual, but you are an attractive man. And you told me that you're very physically active and physically fit. In a way it's kind of refreshing to hear your side of this.

TIM: Yeah, you know. So the idea of commitment, like I said, early on, I think I tried to commit too early maybe. And then I kind of went through a stage where I tried to just do casual dating. And at a friend's advice, I told all the women that I was dating that I was casually dating, and that I was dating more than one woman. And that was fun. It was like going on a bunch of first dates and going out to dinner. It never translated into anything more than that, more than just going out a couple of times with some really nice ladies and having good conversations. But it never really turned into more than that. And I think that it just is that people really aren't crazy about not being the only one, if you're going to go further than just having dinner together.

LAURA: Then you also said that you enjoyed being alone. You love the autonomy and being able to concentrate on relationships with friends and your grown son. But you can't deny that you miss sex. And I think we all can understand that. I'm just wondering if you were able to have conversations with anybody -- like, “I don't want a serious relationship, but I would like to be monogamous with you for a certain amount of time.” Did that kind of conversation ever come up?

TIM: Oddly enough, it did not come up that much. It just seems so awkward to get into that level of talking with somebody about what I want from this relationship. You would think that as a 58-year-old man, I would be able to have that sort of conversation with a woman. But it was not something that I was able to do. I did have a couple of casual relationships. I had one in particular, that I talked with the woman I was seeing casually and said I wanted to move into being romantic, and see if she wanted to go the same direction. And she didn't. That just was -- and that was sort of the end of the conversation. My impulse was to ask her why but the fact is, I kind of know that nothing good would come from that. I don't particularly want to hear why I'm not the guy. So I let it go, you know?

LAURA: Okay, so what are you looking for? Give me your complete wish list whether it's attraction that's most important or -- just tell me what you're looking for.

TIM: Well, I, my initial impulse was to say a pulse. But the fact is, is that is not true. I really am looking for somebody who is smart, who I can have a conversation with. I really enjoy being with a woman who is funny, and who enjoys my sense of humor. And I'm not -- you know, physical attractiveness, I kind of have learned is not that important. And sometimes it can even be a little deceptive. You can meet somebody who's really physically attractive, and then find out that everything that my body is telling me about them is not the truth, you know. And nothing wrong with those people, but they just may not be who I am thinking they are simply based on their appearance.

LAURA: Have you thought about what you want as far as down the road? Do you want a series of long-term relationships? Do you want marriage?

TIM: Well, I should say, I am in a relationship. And this is a fairly new relationship. It's about a, I think we're right at about two months since our first date. But things have been going very well. And I feel like it's sort of the kind of relationship that I'm looking for. So yeah, it's a relationship with a person who is smart, we have great conversations, we have a lot of fun together. You know, as far as, as physical stuff, I mean, we are physically involved. And that is a great part of the relationship. It's not the only thing.

LAURA: We don't want to jinx anything. But have you talked about moving in together? Or are you living together at this point?

TIM: No, no, you know, actually, I'm very happy with my living arrangement. And in this particular case, she is very neat and tidy. And I am not neat and tidy.

LAURA: So I love the trajectory because when we first started communicating, you were -- seemed like you were a frustrated single man.

TIM: Yeah, you know, and it's funny, I listened to your podcast with Bella DePaolo. And I got really excited because she was sort of saying that it might be okay simply not to have a relationship, to live a life where you found rewards and many other things and other relationships. And that sounded great to me until I realized that she was not talking at all about sex. So I wondered, you know, I kept waiting for her to say, “And here's how I handle my sex life.” And I just didn't get an answer on that. So that is frustrating. You know, I'm 58. But I'm not dead, and I still am interested in sex. And yeah, so that's --definitely that was a frustration.

LAURA:  I'm happy to know that Tim is no longer frustrated. And by the way, his new girlfriend? She's two years older than he is. Tim told me something else -- that the very week they met, he had decided he was so happy with his life, it would be okay if he never met a special someone. From great expectations to no expectations and so far, it's worked out.


Dating While Gray is produced in partnership with North Carolina Public Radio. For more on the show, check out That's also where you can find links for sending voicemails and emails. I'd love to hear from you. I'm Laura Stassi. Thanks for listening