I started collecting tape for “Starting All Over Again” in the fall of 2018, as a participant in The Pod Shop. Then, with the WAMU podcast unit, we finessed it to become the first-ever Dating While Gray podcast episode, which dropped in February 2020. Since then, Jim and The Other Laura have gotten married! In June, they celebrated their third wedding anniversary.

But there’s more sobering news for Whitney and Blair, the couple that stole everyone’s heart. “Happily ever after” is a journey, not an endpoint, I’ve come to understand. And here’s where I tell you that Whitney and Blair have split up. It was a shattering event for Whitney, in particular, leading to foundational upheaval.

“There are many nuances to the story,” Whitney writes. “What has been so frustrating as well as a blessing is that in the five years we were married, Blair was never as loving and thoughtful and also, most of all, as reliable as he has been since the divorce. It’s as though he was sleepwalking through his life but saying things that an awake and loving man would say, and then suddenly he stumbled down the stairs in his somnambulance and woke up.

I wasn’t inclined to trust him, but he has been there for me when things have been their scariest and most intense, so I am slowly starting to let him be my friend. There is also something Blair and I recently have been discussing: What each of us has been seeking at a soul level wasn’t possible until we divorced. I have had to be more honest about how I really was scared to be self-reliant, and he was scared to be present and vulnerable to others.

While I am not of the mindset that we will reconnect as a couple, the potential for us to lend one another strength in our soul quests is real. It is yet a long road, however.”

Sigh… and a reminder that, like the Japanese art of kintsugi, sometimes the greatest beauty lies in the repair.

 

CLAUDIA

I met someone for coffee and he brought water with him. And I said to him, “are you going to pay for my coffee?” And he said, “If I don’t pay for your coffee, what’s the outcome?” I said, “we’re done.”

 LAURA STASSI

Dating does not get easier as you get older. Sorry!

ROBERT 

My dates haven’t met my expectations. Let me put it that way.

DEBBIE 

I don’t want to date anymore. I said no, no, no.

 LAURA STASSI

 This is Dating While Gray: The Grown-Up’s Guide to Love, Sex, and Relationships.  I’m Laura Stassi. I was married for almost 30 years before getting divorced. It wasn’t my idea, but I probably should’ve seen it coming. I fought hard to keep it together. Aren’t you supposed to stick together no matter what? Aren’t you supposed to put your own happiness and personal fulfillment aside for the sake of your partner, your kids?

Maybe I was in denial and truthfully kind of scared to be on my own after spending my entire adult life as part of a couple. Being on your own means when your car breaks down on a very rainy night, the first call you make is to a towing company. It means when your dog gets sick as you’re running out the door for a really important meeting, you’re late for the meeting. And being alone also means when there’s a new movie to see or a new restaurant you want to check out, you figure out which one of your friends might be available instead of automatically assuming you’ll have a companion.

Now, four years later, I figured most of this being alone stuff out. Maybe I wasn’t completely whole when I was married. But I’m whole now, and I’m independent. I’m great on my own. But at the same time, I’m ready to find someone to share my life with. I happen to be looking for a man around my age. I’d love for him to be smart, active and funny, reliable, and — it should go without saying — he needs to be available. But how do I find him? That’s what I haven’t quite figured out yet.

So I started investigating. I’m a writer who’s tackled a lot of big research projects. I thought, hey, why not use my professional skills for my personal life? The first thing I wondered was, is it even possible to find love after 50? My first interview was with a woman who had been married and divorced three times before she turned 50. She swore she would never get married again. But guess what? At the age of 67, she walked down the aisle for the fourth time. They happened to meet when they were both on vacations. How random is that? I’ve always believed in this idea that what’s meant to be will be. Is that enough? Or as we get older, do we need to be more intentional if we want to couple up? So I dug around some more. Literally, there are millions of older single people out there. Some are widowed. Some have never found that special someone and some are like me, we’re dating because we’re divorced after being married for a long time.

In fact, the divorce rate for older Americans has exploded over the past several years. It even has its own nickname, gray divorce. And it’s happening all over the world: South Africa, Japan; in Australia and England, they call it silver splitting. You know, the more people I talk to, the more I realize I’m not alone. Whether people are looking for opposite sex or same sex partners, there’s a lot of confusion out there. On this first episode: the struggles and successes of people over 50 looking for love.

It’s a Friday night and I’m at a restaurant slash sports bar a few miles from my high school alma mater. Go Spartans! The place is jammed because a bunch of us have gathered here for our 40th reunion. 40 years. I cannot believe it. My ex-husband is also a Spartan, but we didn’t know each other back then, even though we graduated together. I doubt he’ll show up tonight, even though he knows about it. I know he knows because I told him when I saw him at our daughter’s college graduation a few months ago. I also gave his email address to the reunion committee. Knowing my ex, he’s probably still waiting for his engraved invitation. Sorry, I’ll lay off my ex for now.

I’ve been hearing a lot of stories about older people reconnecting with their high school flame and living happily ever after. But I didn’t come here with that expectation. I did bring my recording equipment, though, in case come across some gray daters. I can’t be the only one. Let’s find out.

SUSAN 

Hi, Laura. I’m Susan. I was only married for seven years and I’ve been divorced since1988 and never got remarried. You’re different when you’re this age. You know, I’ll be 59next month. And I’ve learned to trust a little bit whereas I was kind of putting everyone in the same bucket, if I had gotten hurt from someone, I made sure that wouldn’t happen. If I thought it was, I cut it off. What I’ve done with this relationship is not expect anything. Take it day by day. We’re on our third year and he’s younger than me. We met at work and it’s, it’s going well. We’ll see where it goes. Because, you know, you’re into three years. I’m not going to wait forever. So we’ll see where it goes. We have plans, but there’s kind of complicated. He’s got to settle some things. And he has a child still in high school. He has his place. I have my place. And that’s another big thing. I’m a control freak. It’s got to go my way. And he’s a strong personality, too. And so I’ve learned to let it go. I give him control to a point. When it’s abused, I speak up, you know, because you lose respect. And respect is more than love.

 BRETT 

Look at all your fancy recording equipment. I’m impressed. My name is Brett. I’m on my second marriage. I liked marriage so much I’ve been married twice now. Hang in there. There’s somebody for everybody. I really feel, feel that. And never give up hope. Never give up hope. Cause at some point in my life, I was at a very low low. And I just had to pull myself up and say, no, this is not this is not the end. I gotta pull it up and go forward. And I did. And life couldn’t be better right now.

LAURA STASSI 

You wanna talk? Do you wanna talk?

HS REUNIONER 

No.

LAURA STASSI 

Oh, you don’t wanna talk?

 HS REUNIONER 

About what?

LAURA STASSI 

Dating While …

HS REUNIONER 

No no.

DEBBIE 

Debbie, I was pretty heavy back in the day by mid-2014 when my significant passed away. I didn’t like the way I looked. I didn’t like the way I felt. I lost about 20-25 pounds before I decide to enter a gym because I felt very intimidated by looking as big as I was. I just didn’t want to go in that heavy. Met a personal trainer cause you get two free sessions when you join the gym. After the two sessions he talked me into signing up with them and the more I did them, the more I fell in love with weightlifting. I realized that I really wanted to pursue a bodybuilder lifestyle. I became just became more of a gym freak and stayed at the gym five, six days a week. You know, there’s a lot of people at the gym that I’m interested in, but at the same time, it’s very hard. I feel like to have a relationship in a gym. Everybody is looking to improve themselves, right? There are some that look at me and are jealous. I wish that wasn’t the case, but I feel that. That they think that my body looks better than their body or whatever. And so the jealousy might hurt having a relationship. Having a relationship outside the gym has been a struggle, too. There are people that once in awhile ask me out. A lot of times people don’t. And I think it’s because they know I’m a gym freak. I may not fit in their lifestyle. I do go out. I love to dance. I’m a big, big, big dancer at bars. Some guys that I dance with, they think that means something, right? You know, that’s not how it works for me. I’m not like, OK, I’m just going to go home with you I’m just going to go out with you just because I dance one dance with you. For me to go out with somebody, I really need to know that person.

 LAURA STASSI

 Here’s an update on Debbie. She’s still bodybuilding and has even gone out on a date with gym buddy. As for me, I did not make any love connections. Not that night.

Before we get back to the episode, I want to tell you a quick story about how this podcast got started. A few years ago, I was listening to WAMU in my car and I heard about the Pod Shop, a donor supported program where I could learn how to make a podcast. I barely knew what a podcast was, but I pitched Dating While Gray and WAMU chose me. That’s the  reason I’m here today. WAMU members really did make Dating While Gray possible. So I want to encourage you to support all the great work that WAMU does. You can click the link in this episode’s show notes or give online at WAMU.org.

Ready for a quiz? I’m going to say four names. Three of them are actual usernames of men I came across when I tried online dating. One of the names I made up. Guess which one I made up. McLoving. The Gentle Leo. Dr. Wood. Penguin Lust. Trick question, all of these are actual usernames of men dating online. And let me tell you, I came across far worse. So perhaps you can understand why I didn’t stick with online dating for long. I don’t have the dedication or the stomach for it. It’s so overwhelming. Not that I’m all that. But the first time I got online, I was bombarded with emails and winks and waves and nudges and whatever else people do to try to grab your attention. Sifting through the mess was a lot of work that yielded a lot of horrified laughs, several first dates, but no potential partner. I really wasn’t surprised. Does anybody meet a potential partner online? Then I talked to Michael Rosenfeld. He’s a sociology professor at Stanford who did a study on how couples meet.

 MICHAEL ROSENFELD

Internet is the number one way couples meet for people of all ages. It’s been the number one way same sex couples have met for quite some time. For heterosexual couples, meeting online has been the number one way couples meet since about 2013.

 LAURA STASSI

  Alright, Professor. Not that I’m skeptical. Oh, who am I kidding? Of course I’m skeptical. My personal research totally contradicts your scientific findings. But it reminds me of a

man I met online. His name is Jim. And on our first and only date, he went into great detail, describing his methodical and analytical approach to online dating. I couldn’t believe he put his faith in an algorithm over his gut. And yet maybe this is what it takes to succeed at online dating. I decided to ask Jim about that. We didn’t click, but he was a good sport when I asked if he’d talk to me on tape. We met at a Whole Foods in Northern Virginia. It’s a rocking’ happy hour on the weekends, but on this late Saturday morning there are only some grocery shoppers with some very tired kids.

JIM 

I’m Jim, I’m from Seattle. I’ve been in Washington, D.C. for almost 30 years. I met my my my future now ex-wife at a at a sleazy pick up bar. We started dating and got married too fast for the wrong reasons.

LAURA STASSI 

Oh, OK. But there was something there ‘cause.

JIM 

I got something. Yeah, I got stayed married for a long time. She walked into my office at home one day and said, “I’m moving out”. Three weeks before our 30th anniversary as Always tell everybody I did not object.

LAURA STASSI 

Ah.

JIM 

We’d been living parallel lives for years.

LAURA STASSI 

When did the thought enter your mind, I think I want to start dating?

JIM 

Fairly quickly. I think I started dating at about three months later. Y’know that that would some, might surprise one of my kids, not the other one and some other people. But Imean, it was not like I needed to get over anything but the official stuff. That sounds a little cold. I know, but it’d been, it’d been a long time of not much of a relationship at all. Before I started I wanted, I did actually quite a bit of research in just in terms of reading different articles because I wanted to be a, I wanted to be successful, whatever that meant. And I wanted to be good at dating and be a good date.

LAURA STASSI 

You did it by the textbook, it sounds like, about creating your profile.

JIM 

I did, and also what and also what I did is I sent it to my, I sent it to my sister-in-law and said, “please give me feedback.” I got my neighbor from across the street.

LAURA STASSI 

Yeah.

JIM 

To come take a picture, a couple pictures of me and one with the dog, because you can never go wrong with having a picture with your dog.

LAURA STASSI 

So you were very strategic about doing this.

JIM 

Well, just strategic in that. I wanted to, y’know present myself well in a way that well, would be, you know, well received.

LAURA STASSI 

Explain to me the process.

 JIM 

So, OK. What I did is when I set up a series of searches for myself that had the key attributes and I didn’t have a lot. You know, there’s all kinds of things you can search by. Hair color, eye color, body type. My, my only ones were basically college degree. Noone taller than me, mostly because they weren’t interested in me.

LAURA STASSI

And you would update your searches fairly regularly, right? I mean.

JIM 

Yeah. Yeah. I would, I would go through it. I’d run the search and I’d look who was, you know. Look who was there. And if I was interested. And the, one of the things I liked about Match is it, it had the most flexible and user friendly ability to sort and look at things the way you wanted.

LAURA STASSI 

Sure.

JIM 

I’m a numbers guy. And you could sort numbers in Excel. I wanted to be able to sort and look at things in ways that I wanted to and Match allowed me to, to do that.

LAURA STASSI 

I guess I wanted to believe there was something more mysterious or magical about online dating.

JIM 

I think it’s both. And to me I, I really look at it as both. I mean, every date is potential magical opportunity.

LAURA STASSI 

Did you get on thinking I just want a date? Or were you thinking I really want to find somebody else to share the second half of my life with?

JIM 

Yes, some of, some of both. But, you know, I went out on a on a lot of dates and I can say in that whole time I probably only had three or four dates that I considered a bad experience.

LAURA STASSI 

I wasn’t one of those three or four was I?

JIM 

No, you were not. We did not we did not have.

LAURA STASSI 

Let’s make this clear.

JIM 

 We did not. We did not have a spark.

LAURA STASSI 

We did not.

JIM 

We did not have a match. And we communicated about that.

LAURA STASSI 

Yeah.

JIM 

To be honest with each other, like adults.

LAURA STASSI 

Yeah.

JIM 

But I had a very nice time with you.

LAURA STASSI 

Yes.

JIM 

We went to the Portrait Gallery, had some wine afterwards.

LAURA STASSI 

I remember.

JIM

It was a nice time. But it was just

LAURA STASSI 

 It was fascinating from the research standpoint. One other thing you told me during the date.

JIM 

OK.

LAURA STASSI 

You asked me if I knew.

JIM 

 Oh my god.

LAURA STASSI 

What.

JIM 

Oh my gosh.

LAURA STASSI 

The third date rule was.

JIM

I forgot about that.

LAURA STASSI 

And I said to you, you don’t even think about having sex with someone until after you’ve been out at least three times. And you said…

JIM 

If, if a woman’s not willing to sleep with you by the third date, you move on. But it was that that’s that everything that I’ve said comes from men’s magazines. I’m quite confident that was I forget which one, but I know I read that in. And they did have once again, what you know after you see something.

LAURA STASSI 

Right.

JIM 

You see it everywhere.

LAURA STASSI 

Right. Well, that’s really sad because we’re all grown-ups. You could have three dates in three nights.

JIM 

Yup.

LAURA STASSI 

Do you know what I mean? So it’s like, seriously?

JIM 

So I’d, I would have to speculate that I when I asked you that question I wasn’t asking you to like to find out if that was a compatibility test.

LAURA STASSI 

Oh, no, no, no.

JIM 

I think it was cause we were exploring, cause you were so new to dating. We were exploring and you were asking me questions.

LAURA STASSI 

Yes, yes.

JIM 

 

And you were trying to learn things. And I was like oh. So as you’re dating.

LAURA STASSI 

Yes.

JIM 

You were there the third the three date rule.

LAURA STASSI 

Yes.

JIM 

Just to clarify for the listeners.

LAURA STASSI 

It’s what made you memorable. Tell me about Laura.

JIM 

Laura.

LAURA STASSI 

Not me Laura.

JIM 

Girlfriend named Laura. Right. We met on Match. Actually, she contacted me. So, so for all the systems in the world that you have. She contacted me.

LAURA STASSI 

What was your first date like?

JIM 

She was. She was 45 minutes late.

LAURA STASSI 

Oh.

JIM 

And she was just so impressed that I was nice and waited and didn’t complain that she was late. And I just like it’s traffic in D.C.

LAURA STASSI 

And how long did you date before you decided you wanted to be exclusive?

JIM 

I think it was about six or seven weeks.

LAURA STASSI 

Oh.

JIM 

Seven or eight weeks.

LAURA STASSI 

So if you don’t mind me asking what came first? The commitment talk or the sex?

JIM 

Oh, wow. Sex.

LAURA STASSI 

Oh.

JIM 

We did. But then we actually stopped having sex cause I said that I was uncomfortable seeing more than one person and being in a sexual relationship. That’s a, it’s one thing to be dating more than one person. It’s another thing to be.

LAURA STASSI

Having sex with.

JIM 

Sleeping with another person at the same time.

LAURA STASSI 

Do you miss dating?

JIM 

Not. Not really. No. I mean, the ultimate objective was a long-term relationship. And I have a good one. With woman I love. So, no, I do not. Do not miss dating.

LAURA STASSI 

Good for you.

Jim and the other Laura dated for about three years before moving in together. A year later, Jim reports that all is well. And he is happy to be out of the gray dating scene. Can’t blame him. Clearly, online dating worked out for Jim and the other Laura. And you heard the Stanford professor. Online dating is how most straight and gay couples of all ages get together. But part of me is still clinging to the idea of serendipity, especially when I hear stories like the next one.

WHITNEY 

And so I started to actually time things so that I could see him take the dog for a walk and just think this is deranged.

LAURA STASSI

That’s coming up next.

Losing a partner is devastating no matter how old you are. And maybe at this age, it’s easy to slip into thinking I’ll never find love again. But you never know what will happen next. Meet Blair.

BLAIR 

Married for 35 years. Three kids. We moved up here for a job change September of 2013. And just as we were coming up here, we learned my wife had brain cancer. She passed away in January of 2015.

LAURA STASSI

 Blair lives in an apartment building in Maryland.

BLAIR 

This apartment building has a shuttle van and it was a, believe it was a Friday afternoon. And I got on the van and Whitney was on the van with her parents and her partner at the time. I was just kind of really taken by her beauty immediately.

LAURA STASSI

 Whitney also lives in that apartment building. She’s been divorced for a while, moved here from up north for the job of her dreams. She has a long-distance boyfriend and he keeps breaking promises to end the long-distance thing by moving down here for good.

WHITNEY 

Sounds crazy. I just remember this jolt like, wow, wow. Something about this man.

BLAIR 

After that, walking Linus periodically. And I would run into Whitney when she would becoming home from work or out running errands or something. And it would be a nice sort of chance meeting. I have to say, I was kind of looking for her to, to come by any time I was out there walking the dog.

WHITNEY 

He’d say, “maybe we should get together for a cup of coffee sometime or a glass of wine.” And I would say, “oh, I’m out of town. I’m really sorry.” Because I was in this relationship. My job as a medical reporter took me all over the place. I was virtually never home. I was really concerned with just, you know, I was already there was separation between me and, and the man I was I was seeing. So I would not telegraph at all that I had had that zing and was really attracted to Blair.

BLAIR 

I met some women in bars, but nothing ever developed. I was always hoping that Whitney would be available or interested.

WHITNEY 

I started to enlist friends in the building and I’d say, “let’s get together on the roof,” cause, you know, we have this beautiful roof and view and we have this sun deck. And I’d bake something for dinner or I’d, you know, or I’d, we’d have wine. And, and I truly actually thought this man is probably lonely and it probably would be very nice for him to have somewhere to go and people to talk to. So I started inviting him to join myself and other women in the building and other friends in the building. Every time he came up, I noticed that he was completely impeccable and he was just always such a gentleman. Impeccably dressed. He was impeccably clean shaven and not a hair out of place. I know this man is courting me.

BLAIR 

She was absolutely right. I was trying to make myself look and present myself as best I could knowing I was going to see her.

WHITNEY 

All the women in building are in love with him, too. And they would see us up on the roof and they they just would say, “oh, my goodness, he’s the cutest thing, he’s so wonderful, he’s so lovely.”

BLAIR 

One time she was saying how she was frustrated that her know boyfriend was know upon New Jersey and not willing to come down. And I said to her, “I can’t understand how Aman wouldn’t wanna spend as much time with you as possible. How they could stay away and not want to be with you all the time.” I said, “I can’t understand how a man could know you as well as he does, or even as I do, which isn’t as much. And not wanna spend all the time he could with you.”

WHITNEY 

I had moved recently into an apartment that gave me a view of the street. I noticed more and more that I was able to see Blair taking the dog out for a walk. And so I started to actually time things so that I could see him take the dog for a walk and just think this is deranged what I’m doing this crazy. Normal people don’t do this like wait to go to work until they’ve seen the guy walk out with the dog. It really started to make me panic that other women were gonna see what I saw. I just started thinking, how could this man Stayfree? I started really getting sad because I started thinking, I really like this man. And one day, Blair was walking into the building as I was walking out. And I don’t really even quite know why I did this, but I put my arm through his arm. I said, “I’ve been meaning to talk to you. Could you walk with me?” And I said.

BLAIR 

Turned me right around.

WHITNEY 

“Every time you ask me out for coffee or for wine. I’m not a flake. I know what you’re really asking me. And I’m not telling you no, it’s just I need some time.”

BLAIR 

Got a text from her. “Okay. You can take me out to dinner now. It’s Okay.” So we went out and we had a wonderful time talking and we were just really connecting. And at one point I reached my arm under the table. I said, “do you mind if I hold your hand?” And it was just it was really electrifying. And then Whitney sang me a couple of songs from The Sound of Music.

WHITNEY 

Well, I don’t remember what prompted that but all of a sudden I found myself sitting there singing to him and he was astounded.

BLAIR 

 You got a beautiful singing voice. She does. She sang Edelweiss.

WHITNEY 

Edelweiss, Edelweiss.

BLAIR 

I knew I wanted to be with her for the rest of my life. I knew that this was a person I didn’t want to let go or wasn’t going to take lightly. I also knew I probably had grown emotionally and emotionally matured from my first, from, from being married, that there were probably, you know, my wife used to accuse me of sometimes not sharing my emotions as much and, when after she was gone. And I thought if I ever found the right person, I wasn’t going to let the opportunity go by without making sure that I really let my emotions be known.

WHITNEY 

From the beginning, I would say, “alright, here’s everything you want to know about me, all the ugly stuff, all the bad stuff, all the scary things, all the things that I still, you know, don’t talk about. My shames, my fears, things that happen to me that you probably aren’t nonbeliever. But it’s true. It did.” You know, like all of it. Just download, get it out of the way. Get it up front. Do you still want to be with me? And his response after a few days of kind of unloading all that was, “I want you to know I love you so much that you can take all the love now and go back in the past and just pour all the love I have for you over everything that hurt and let it fill those cracks. Just know that you’re going to get to this point. You’re going to be OK.” I was a single woman doing her thing and succeeding and he came along at a point in my life where I didn’t need him. And I actually used to say that to him, “I don’t need you.”

BLAIR 

She’s lovely. She’s funny, she’s fun, bright, caring, emotional. By the way I’ve got a list on my phone of over 40 adjectives, I think, that describe Whitney.

WHITNEY 

It really was this energy that Blair brought to my life. And everyone sees that I’m whole. And I didn’t need this man, but maybe I really did.

LAURA STASSI

 Blair and Whitney got married. They had a small ceremony with just their family, including Whitney’s son and Blair’s kids. They were all thrilled. And Whitney ‘s ex-husband and her former long-distance boyfriend both sent their best wishes. Whitney changed her last name to Blair’s, and after the honeymoon, they moved in together into an apartment in the building where they used to be just neighbors. Sometimes dating feels so daunting to me. It’s a really big world out there. Finding the right person is going to take a whole lot of effort and time, maybe money, disappointment and heartbreak and anxiety. Or I’ll have to figure out exactly where to stand so that when my special someone falls out of the sky, he will land right on top of me in a good way. But, you know, I’m not complaining. It’s exciting to be having so many new experiences at this stage of life. I’m doing things I’ve never done before. I’m meeting people I never would have met had I remained coupled whether there are potential partners or friends. I’ve expanded my circle. I’ve built a new community.

 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.