When it comes to finding love or making a commitment, is there ever an expiration date? Laura talks with Julie, who’s been on the dating market for almost a quarter-century. Then she checks in with Clyde and Trish, who’ve chosen the slow road despite instant chemistry.

Julie’s partner’s couch … great for watching movies!


This is Clyde’s couch. It’s in Trish’s house … for now.




This is “Dating While Gray: The Grown-Up’s Guide to Love, Sex, and Relationships.” I’m Laura Stassi. And on this episode, true stories of taking a “Long Leap to Love.”

If you ever worry there’s some kind of expiration date for being on the dating market, that if you haven’t found the one you’re looking for after months or years, then your time is up … well, I’d like to introduce you to this woman.

JULIE 00:29

My name is Julie, I reached out to you about a year ago. And I thought, Laura Stassi has to talk to me because I’m the queen of Dating While Gray. I’ve been doing this for so long.


Twenty-four years — that’s how long Julie’s been dating after her two-decade long marriage ended in divorce. Julie’s career in fundraising allows her to live wherever she wants. After traveling around, she’s now in Oregon. Julie’s tried basically all of the major dating sites. She’s had two long-term relationships. But when she sent me a voicemail in the spring of 2023, she had yet to meet the one. And while she’s happy on her own, she’s still hopeful even if the positivity was wavering a bit. I included Julie’s voicemail as part of the “Dishing on Dating” episode. And I neglected to inform her ahead of time.

JULIE  01:27

Okay, I admit, I listen to podcasts to help me fall asleep. So I’m listening in bed to the podcast. And I hear this woman talking, and she says she lived in Ann Arbor, Michigan, Boulder and Hawaii. And I kind of like, woke up. And I’m like, wait, wait, that’s me. I did not recognize my voice at all. I did not at all. So I had to re listen to it. And I was like, thrilled. I was like, oh, that’s so cool. So yeah, so I was just falling asleep one night. And then I shared it with everyone I knew.


Oh, I love it. And it also motivated you to email with an update. So in this original voicemail, you said, I’ve had two dates with one fella. How did you two meet?

JULIE 02:16

We met on eHarmony, which is one of the sites I’ve tended to gravitate towards in the years to come. Match and eHarmony. Basically, although I’ve done them all: OKCupid, Plenty of Fish, all of them. I contacted him first. He was a golfer. So we’d laugh about this that the first thing I said in my message was, oh, by the way, I live on an Arnold Palmer Golf Course. And I see you like to golf. So maybe you drive over the mountain pass to golf and buy golf course. So we laugh about that. And I actually called it a Jack Nicholson Golf Course, which is an actor, not Jack Nicklaus. And so he knew immediately that I didn’t golf, you know, he’s like, she knows nothing about golfing.

He was the executive that ran a private Catholic school, so then I thought it was important to let them know, you know, I’m an atheist. So is that going to be a problem? So we kind of got some of those things out early.


When you say you got things out early, was this before you even met? Or was this like part of the getting to know each other?

JULIE 03:24

Part of getting to know each other, I think, yeah, just in the first — I only exchange emails and texts for a couple of weeks at the most. And we did have a bit of a delay of getting together because it was winter. And we couldn’t get together. But eventually, we met halfway before meeting him.


Had you done anything proactive, like change dating sites, or tweaked your write-up or your pictures? Or did he just kind of appear one day?

JULIE 03:54

Well, I’m always updating my profile on the sites and trying to make it current and more interesting or trying to add personality to it. Probably six months or so, I’d been on there and reaching out, and I always tell everyone you have to reach out you have to be the one that’s proactive and reach out.

First in-person date, we went to a resort that is literally halfway between our homes. So about an hour, 45 minutes away from here. We had lunch, and it was a lovely lunch. I can’t remember a thing of what we talked about. I told him that the other day, I’m like, do you remember what we talked about? I don’t know what we talked about. I’m sure we just shared our life story and where we’re at.

But after lunch ended he said hey, there was a bar upstairs, a restaurant downstairs, would you like to go up and have another glass of wine? And I said that would be great. So we talked, we probably spent about three hours at this place. Just talking and really enjoying good company. And yeah, and we knew we wanted to see each other again.

I think we’re both kind of surprised that we both were different kinds of people. You know. He’s a super intellectual, wonderful teacher, he’s been a wonderful father. We just enjoyed each other. And we laughed a lot. I think that was key, we find humor in things and we’re able to, you know, and I’m a very honest, upfront open person about things. I asked about his wife and all that I had gone through a cancer battle with my daughter. So we had some commonality in that and understanding, you know, the stress that that puts on a family and how hard that is. So we had common things, but we were very different. Where he grew up, and we were both college athletes, we had a lot in common. So we shared a lot of things, and enjoy travel. We both enjoy travel a lot.

And so, you know, I think one of the next things we did aside from visiting each other’s homes and kind of dates, dinners, theater, some fun things, you know, and then finally, the first weekend at someone’s home.


Was that nerve-racking?

JULIE 06:21

Oh of course it is. It’s always so awkward. It’s so awkward. But I remember I invited him, I said, come for come for the weekend. I have four bedrooms, you know, you don’t have to sleep in my bed. But, and you can golf, you know. And finally, finally, you kind of break through that ice of having an intimate relationship. And, yeah, and then you know, and then we started planning more things together. We really enjoyed the time. It’s really awkward for me, particularly, having lived alone for a long, long time. Yeah, I think I have, you know, single behaviors that are weird. Or just me.


I remember when I first got divorced, I wouldn’t let the dog sleep in the bed with me because I thought I don’t want to get her in the habit of sleeping where somebody else might be.

JULIE You never know.


I know. And you know, after a couple of years of that, I’m like, I’ll get up here. Do you care to share anything specifically about what you mean by weird single behavior?

JULIE 07:19

Oh I just, you know, I just, well, one of the things. I too, I get I work all week, right? I’ve been a full career person. And on Saturday mornings, all I do is watch cooking shows and drink coffee. Literally from seven till noon. I love it. I just I love cooking. So I just enjoy and you know, some people find that kind of odd like, Wait, it’s a beautiful sunny day, we should be able to hike. I’m like, oh, no, yeah, we gotta wait. But it’s just awkward having someone in the house and kind of, you know, you know, I make my coffee a certain way that night. So it’s just getting used to having someone in the same space physically with you. It’s interesting.


So how many times did he come over before you said, hey, I’ve got this thing I like to do? Or did you from the very beginning, say, I’m going to be drinking coffee and watching cooking shows all day?

JULIE 08:13

So from the beginning, there was no hiding anything. You can go golfing if you want. I’m gonna watch cooking shows. I’m more I’m more flexible than that. But we laugh a lot about our being quirky and having our ways of doing things. And I mean, he’s still developing his ways of doing things and figuring out, you know, he downsize from a huge 50-acre ranch to a small home in a new neighborhood. And he’s setting up a house on his own again. So, you know, he’s going through, there’s a lot of transition this year, a lot of things that are happening.


So as this relationship is progressing, did it ever make you I don’t know, because it is kind of a stark difference. Being on your own for a quarter of a century versus being part of a couple for over a quarter of a century? Was that ever a tricky thing to talk about or maneuver navigate?

JULIE 09:17

Oh, we’ve been quite we’re quite honest and open about everything because once we realized we really liked each other and we could see that maybe there was a good enough foundation for a wonderful life together. He’d been married twice, so there, there was some divorce. We both come with so much experience in and we both are glass half full people wanting to live and enjoy and take in the small moments. And, you know, we’re determined we’re very we’re different in some ways, and we are just determined to Be very communicative, very transparent with our feelings. He has about 10 times the resources I have, oh, but we’re upfront about it all.


Tell me what the housing arrangements are going to be.

JULIE 10:17

Yeah, so I’m selling my house. In turns out, I’m selling it to my daughter. So it’s sort of not as big a deal as it could be. But yes, and my house is bigger than his house. And his is a perfect retirement house. And so I’m quite thrilled with the idea of downsizing. And, you know, it’s, he doesn’t have the kitchen of my dreams, but it’s okay, you know, it’s fine. I live in the middle of nowhere, and but I have a beautiful, stunning view. And but it’s a challenge being here. And there’s many more resources and things where he lives. So it was an easy decision to make to move in with him.

And we’re having the funny part of, you know, figuring out how to, you know, what I bring over to his house, he’s got the ugliest single bachelor leather couch with cupholders and lights and, you know, plugins for your computer that is like, ugly. And I have this very sleek, modern home with my, you know, white linen, low Design Within Reach couch. So the first thing I had to get over was like, that couch is not coming to my house, because it’s just not a guy’s couch, its couch is staying for now. Because I really care for him. And enjoy watching movies on that couch with them. But he has promised eventually, we can get rid of the couch.


well, you know, it’s interesting, because you’re saying — and I understand you haven’t moved in yet, but you’re saying his house, his couch. And I have to tell you, I know Design Within Reach. Design Within Reach, they’re probably going to say — okay, honestly, I know you love him. And I know stuff is just stuff. But surely this has got to be, I mean, do you ever wake up at night going, Oh, my God, what am I doing?

JULIE 12:11

We’ve actually purchased some things that we know, we need that he needs that I don’t have, and that would work best for our stuff. So we’ve done a couple of purchases and we’ve, you know, flagged everything I’m going to take over. I mean, yes, there are moments like, Wow. I because I’m so used to having time alone, but we talk a lot about that about how, yeah, you can go golfing for a weekend with your buds. That’s great. You know, I can’t do everything all the time together. And, and I do volunteer work, and I’ll continue to do that. And it’s, you know, yes. I do worry about am I going to have enough of my alone time? Because it’s smaller home. You’re not working? Yeah, I mean, cuz working, you got away and I travel a lot for work. So it’s gonna be different, but we’re gonna play in a lot of trips.


What did you really most appreciate about being single and what made you most anxious about being single?

JULIE 13:16

Most appreciated about being single? Well, I do love the flexibility I have in you know, I can do whatever I want, whenever I want. And, and I enjoy. You know, no one’s looking over my shoulder judging me watching too many episodes of some or binging on Netflix, you know, I mean, I can do that I can watch all the Godfather movies in a weekend and repeat. I enjoy the 24 years of which I got out and met new people I kept you just have to keep a positive attitude and think of it as meeting new friends. And don’t be too serious about it. What I laugh when I first started online dating, it can suck you in and you can spend hours on those sites. And I did not I could see that that was a problem. And I did not want that to happen. I had this beautiful hourglass thing that I got from MoMA. I don’t know why remember that. I don’t have it anymore. But I would turn it over for one hour of the Sands shifting in and that’s all I’d allow myself time on. And then I sometimes I would just take a break and go back but I tried to make it a rule that it wasn’t overtaking my life finding someone else that was you know, sort of sugar on top kind of It


doesn’t sound like you were anxious. It almost sounds like and please correct me if I’m wrong, but almost sounds like you knew in the back of your mind that you are going to find someone

JULIE 14:39

Well, there have been moments. And literally, right before I met this recent person. I you know I started thinking oh, maybe I’m not you know and maybe it’s time to get some cats. I really want a dog but I can’t have a dog where I live. I couldn’t understand why I hadn’t met someone because I feel like I have a wonderful package of things to offer someone. And I would get over that really quickly because it’s just happenstance. It’s just timing. It’s just opportunity. And it’s just, you know, it just, it was to happen. I did really feel like one day I would meet someone, I wasn’t worried per se. But you do start to wonder, well, maybe it’s just not going to happen. And I was okay with that. I was okay with that.


Julie and her partner are both retiring. She says they are not talking marriage right now. But they do have all the legal paperwork in place to address their plan to live together as a committed romantic partnership. By the way, you heard Julie mentioned MoMA and Design Within Reach. MoMA is the Museum of Modern Art. Design Within Reach is a home furnishings retailer. Though reach might seem like a stretch when you look at the price tags.

For some of us, like Julie, the long leap to love as measured by the time it takes us to find someone. But for others, the long leap is measured more by mindset.

TRISH 16:16

I thought well, this is it. It’s great to meet Clyde. However, I may need some time to heal and to kind of find myself again, so I was protective of that.


That’s Trish. We’ll share her updated story with Clyde after the break.



Maybe you remember the 2022 episode with two people I called Trish and Clyde. They met while taking pickleball lessons in a class with three other people, including me. Clyde’s been married and divorced twice. After that second divorce. He retired, sold his house bought a minivan and traveled all over the country playing golf. As for Trish, she’s been married and divorced once. It’s a long and especially sordid story of her now ex-husband’s infidelity.

Neither Trish nor Clyde was looking for love when they randomly met in our Pickleball class. Romantic sparks flew instantly. But they didn’t act on them immediately. Instead, they started playing pickleball together. They’re neighbors, so they also took long walk and talks, really getting to know each other. And they began spending evenings together, watching movies and eating the dinners Clyde would  cook for Trish while she was at work.

At the end of that 2022 podcast episode, Clyde and Trish were happily taking it one day at a time. I decided to check back in with them to see if their relationship has evolved even more.

TRISH 18:00

I remember eating dinner one time with him. And he looked over at me and he said, so where do you think this is going? And I hadn’t really given it a lot of thought because, you know, I was working during the day. And I would see him at night. And I just, it started making me realize, well, I really just need to seriously think about this. And I told him that I just absolutely was having the best time of my life. And I’m not angry like I thought I would be at that time because of my history with my ex-husband. And I just loved the feeling of not being angry.


Did this question in any way feel like pressure to you?

TRISH 18:49

Not really. I think it was more of a question. Just you know, maybe he had thought about it. Maybe it just popped into his head.


Tell us. Had you thought about it?

CLYDE 19:00

I had thought about it because I had been divorced longer than her. And I kind of given up on romance, as I told you earlier. And then I met Trish, and everything changed for me. But I knew she was still relatively fresh off of her divorce. Compared to me, especially, and she just needed some time. And I knew from my experience over time that she would get there if she felt the same way about me as I felt about her. So I was just wondering, you know, where her head was. And I think every month or every couple of months I might ask her, how are you doing and how are we doing, and let’s check in.

TRISH 19:45

I was very cautious though not so much because of him but because I was protecting my own well-being because I wasn’t sure if I was just gonna flip out and just not be a normal functioning 62-year-old who might just be too bitter about my situation. And I thought, well, I’m enjoying this. But how long is this going to last? I wonder if I’m going to start having these demons from my past surface again, you know. So I was I was very concerned about that. And I thought that my independence was going to be sort of swallowed up again, like it was in my marriage.


When you were wondering where it was going, did you feel a need to put a label on it?

CLYDE 20:44

No, I did it. No, not at all. I had my own place. And I’d furnished it like it was going to be my forever home, my condo. That was one of her first comments when she came over. Boy, this is good furniture for a man. I didn’t feel a need for a label. But I felt the need, like I’ve always felt the need to be exclusive.



Like, I’m not a dating-multiple-women-at-once kind of person, it’s one at a time for me. And since I wasn’t even planning on anything and hadn’t been dating anyone since my last marriage, then I was like, I’ll just see where it goes. But I did kind of want to see where her head was because I knew things were still raw for her.


It’s not like you were gonna get on a dating site if she wasn’t interested. But you probably wanted to make sure that you weren’t — I don’t know, kind of chasing after rainbows.

CLYDE 21:43

Exactly. Yeah.


What’s that song, chasing after waterfalls? (singing) Don’t go chasing after waterfalls. Is that a song?


That’s a song. Yeah.



You want to be … I don’t know, respectful. You want to live in the moment, but on the other hand, you don’t want to all of a sudden find yourself, oh my gosh, I’ve been — what just happened?


Falling in love with someone who is not available. Yeah, right.


Not emotionally or otherwise available.

TRISH 22:08

I think we had some conversations where we thought, you know, this is really nice to spend majority of the week together after work, and he would stay over. And I liked it. And I thought when he wasn’t there, I kind of thought well, I’m a little lonely. I kind of like it when he is here. And so it just kind of evolved. And it wasn’t necessarily planned at any one time. But I remember thinking to myself, we’re just going to keep going and see where this leads.



It morphed into me staying over at her house, probably more than she stayed at mine because she had a little dog that she had to take care of. And we’ve renovated or she had her place renovated and I helped a little bit. And she ended up being at my place for about a month during that. So that was sort of a trial period kind of thing. And her and her dog came over and stayed in my condo while her place was under construction or kitchen.

TRISH  23:13

And that was about six or seven months after we started seeing each other more seriously. So it was pretty quick, actually.


Did that make you nervous in any way? I’m thinking if, okay, I’m just trying to put myself or the average listener in your shoes. I’m dating somebody, it’s going well, and then they say I’m gonna renovate my kitchen. And I’m like, oh, wait a minute. I guess we’re not going to — I mean, do you know what I’m saying?

CLYDE 23:40

Well, I was all in and helping her with the renovation and doing stuff with her, and it was fine with me if she came to my place for a month. I like, I wanted her to, and I was fine with it. She was actually probably a little more cautious about it than me and had second thoughts.


I’m talking about the financial aspect of her investing in a property she owns by herself.



Oh, that didn’t bother me at all. That’s her property and she gets to do whatever she wanted. New stuff in the kitchen. And she was replacing the floor anyway and it kind of turned into a whole kitchen remodel.


Did that feel a little weird to you to do that?

TRISH  24:19

It actually seemed really natural, for some reason. And he helped me every step of the way. He went to Home Depot with me and helped me select the countertops. It’s almost like I felt we were a happily married couple and we’d known each other for, you know, 10,15 years.

It just seems like everything we did together, we connected. We could be shopping in the grocery store. We could be playing pickleball. We could be taking walks. We could be traveling in — you know, we went to Hawaii together. We went to Bermuda. We went to Portugal, then took several trips down to Florida. And everything just seems so easy and calm.



And the way we travel together, I like to plan the details, the hotels and the rental cars and the airline bookings. She likes to plan the itineraries. And so that works out perfectly, because I don’t really care that much what we do, as long as she’s there with me, companion. So it just works out fabulously. And, she’s turned me on to podcasts. I hardly ever listened to podcasts until I met her.

Well, except for one!

You got your kitchen renovated, you moved in with him and the dog, while the kitchen was getting renovated, then you go back into your now nicely renovated kitchen…

TRISH  25:44

I believe we had a conversation about, well, we’ve been spending all this time together, maybe we should keep living together.



I want to add to that too. After the renovation, when she spent all that time at my place, then I basically spent pretty much every night at her place. And I would pack a little bag and then when she’d go off to work, I’d go back to my place and spend the day and do my thing — and you know, read, and go on walks and do the stuff I did. So we were sort of almost living together, but not quite.


When did it happen that it was going to be more or less permanent thing?

TRISH  26:28

We never — I never felt tired of him. And we just really wanted to spend all that time together.

CLYDE 26:36

And it was time. It had been a couple of years at that point.


Was there discussion about your place versus my place?



Not really. It was always going to be her place. Fine with me. Well, and I am renting. I’m renting my condo once I moved in with her.


Okay, so you decided to keep it but rent it out.



LAURA STASSI Furnished or unfurnished?






That was yet another discussion

TRISH  27:08

when I bought my condo in 2018, I thought, well, this is just going to be a temporary place. However, I loved the idea of being able to design it and furnish it the way I wanted. And I love the ocean and love the colors of blue. So I thought well, this is this is really fun for me to be able to decorate how I want. So when we talked about which condo we would want to live in, mine was pretty much always going to be the one that we were going to live in.


Did you ever think well, you could do that with Clyde’s condo, you could repaint it.

TRISH  27:44

I have a really nice patio, and it’s very tranquil out there. And the birds love to come. I have a nice little spot where they can eat their bird seed and we can watch some.

CLYDE 27:57

Plus as a sweetener, she let me have her second bedroom for my office.


The M word, marriage. Is it on the table?

TRISH 28:10

It is. We’re just still being cautious.


WE are being cautious?

CLYDE Yes, we are being cautious here. It’s already happened for me twice. And even though I’m sure Trisha is the one, there’s still some caution to be used here.

TRISH 28:37

I love the idea of being married again. But there’s part of me that sort of like at age 62, do I need to do that? I just so want to be sure because I don’t want to get divorced again. It’s like a death. And I just, I don’t want to have those negative feelings again.


Yeah, and I totally get it. At the same time, to be devil’s advocate, even if you were to not get married, I would think if your relationship with Clyde were to end it would probably be as emotionally impactful as a divorce. Or would it not be?

TRISH  29:16

Well, it would, you’re right. It would be emotionally but from a legal standpoint, it would, you know, it would be a lot smoother to break up than it would be to get divorced. And I just I don’t like the whole process of divorce. I’m still ambivalent, but I know that I love him more than I’ve loved anyone else, maybe, besides my children.

CLYDE 29:46

So there you go, we had the M word and the D word. All in the same sentence.


And the L word.


And the L word.


Trish told me she’s getting ready to retire, and Clyde’s getting back into a minivan. This time it’ll be with Trish. They’ll be traveling around the country visiting national parks and, what else, playing pickleball. And just like Julie isn’t a fan of her partner’s furniture, you heard Clyde say Trish isn’t a fan of his.

Can I just say, what is it about men and women and their different tastes in furniture? Do you remember how dating coach Damona Hoffman said we should all be looking for more green flags? So maybe there’s a correlation? Bad couch, good guy.


 Dating While Gray’s audio production and mix is by Steve Lack: Audio. Theme music by D. Peterschmidt. Please like and follow Dating While Gray wherever you get podcasts. That way, you’ll never miss an episode. And, if you’re so inclined, leave a review letting everyone know what you love about us.

For more on the show, check out datingwhilegray.com. That’s where you can find the Dating While Gray archive of episodes. You can also find links to send me questions, comments, tips, and true stories – through email and voice mail. You know I love hearing from you.

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I’m Laura Stassi. Thanks so much for listening.

 Episode transcripts are posted on the Dating While Gray website before they are thoroughly proofread. The audio of this episode is the authoritative record. For terms of use and permissions, please email laura@datingwhilegray.com.

Episode transcripts are posted on the Dating While Gray website before they are thoroughly proofread. The audio of this episode is the authoritative record. For terms of use and permissions, please email laura@datingwhilegray.com.