This week, we’re revisiting an episode from pandemic days …. because even though online dating can be confounding and frustrating, it remains a tempting option for a lot of older singles.  

‘Love After 50’ author Francine Russo says online dating is all about the attitude.


Despite a first missed connection, Claire and Jim prevailed.


SPEAKER 1: 00:07

Online, everybody’s talking about online dating. I did my first eHarmony, and then I got back on

SPEAKER 2: 00:14

How many dating sites? Two. Zoosk and International Cupid.

SPEAKER 3: 00:20

So Meet Mindful, it’s for people that probably are more into yoga and meditation.


Since COVID-19, a record number of single people have turned to online dating: clicking, swiping, boosting, super liking…

SPEAKER 4: 00:39

I used like Plenty of Fish, Bumble, and I tried those. Encouraged by another friend, like, “All these guys are out here. Try Bumble again.” And so I tried it again.

SPEAKER 5: 00:51

I think four different ones. And right now I’m on two of them.

SPEAKER 6: Like I’m on Tinder. I was on the — Our Time, Tinder.

SPEAKER 7: 01:01

Tinder and OKCupid at the same time, and was like, okay, I’m just gonna spend 15 minutes a day looking at this.


So many sites, so much time and energy spent. But does online dating actually lead to love? That’s what we’re exploring on this episode of Dating While Gray. I’m Laura Stassi.

About six months before the coronavirus lockdown, the Pew Research Center did a study on online dating. And let me just say, we’re using the term online to refer to both dating websites and dating apps on mobile devices. This study found that only 16 percent of Americans 50 and older had ever tried online dating. And of this number, only about 6 percent had ever entered into a committed relationship with someone they met online.

Now, if the Pew researchers had narrowed the survey to people who’d become single after they got older, they just may have found more online users — like journalist Francine Russo. Her new book is called Love After 50: How to Find it, Enjoy It, and Keep It. Francine interviewed over 100 experts and older people. And she also included details of her own life.


I had the unfortunate experience of being widowed twice, once at 49, once at 60. And I found love when I was looking for Michael, I’m not gonna say it was five minutes, but it was pretty close.


Michael is Francine’s partner. She met him after her second husband died. And they’ve been together about six years now. Francine discovered online dating after her first husband died. And after that, she says, making romantic connections was easy.


Now I live in New York City, where there are millions of single people within several blocks of me or certainly several miles. And the really hard part was figuring out who was worth connecting with, and who was the kind of person that I wanted to be with, and working on myself so that I became the kind of person who could have the relationship that I was ultimately able to have. I had to do a lot of work on myself.


And did you do the work? Because I think I read that you started dating that second time, like six months after your husband died. So was it, did you do a lot of work very quickly? Or did you feel like you got online or you know, started dating too quickly?


Oh, I started dating too quickly, of course. But I — and what I was trying to do was outrun my grief. And I found that wasn’t possible because this was a short relationship. It reassured me that somebody found me attractive still.


Do you think those experiences being widowed and being on the older side of the boomers, did those experiences in any way affect your ability or your interest in re partnering?


Yes, and no. I’m somebody who loves being partnered. And if anything, I was way too needy and desperate to find a partner. And you know …


FRANCINE: Oh, yes. And people say, you know, so my friends told me oh, you can’t be needy or desperate; that’s so unattractive. And I said well, but I am needy, what do I do? And I had to learn to be okay by myself. I never became somebody who preferred being alone. But I learned to be okay. I learned that — I rediscovered my love of biking and when I was out on the river with the wind in my hair, I didn’t need anyone else there. And I learned to take myself out on a Saturday night, because I hated staying home, and going to an arthouse cinema and buying one ticket, and then sitting outside that cafe and chatting up people. And I’m not going to say I wasn’t lonely because I often was, but I was okay.


I wonder sometimes that success happens because it’s okay, I am going to find somebody rather than, oh, let me just see what’s out there.


Well, attitude does matter. And there’s a whole chapter on having the right attitude, which is called “Date Like A Realist,” because the negative attitude like there’s nobody out there, or it’s too much work, or I don’t want to bother, I’ll just see if it happens, that won’t get you anywhere. But on the other hand, being determined, and fantasizing that this person online is your next partner, that living in fantasy is also the wrong thing. You have to be hopeful, not negative, but realistic.

When I went online, I found that there were hundreds of eligible, appropriate people for me, some of them living within blocks of me that I might have stood behind in a supermarket line. People who want to find somebody announce themselves. You don’t have to scrutinize their hand for a wedding ring. You don’t have to ask pointed questions like, oh, do you have to get home to your wife or your partner? Now, it’s true that there are some liars online. And you know, I have — I deal with that in the book, how you deal with that. But most of the people are well-meaning. They really want a relationship. And that’s what you’re looking for, a real connection.


I look for people who are new to the site. And they weren’t jaded, and they weren’t already dating somebody. The other thing is, long correspondences result in fantasies that can go pop at one glance, and they — just doesn’t make sense. Also, if somebody is not interested in meeting — they delay, they delay, they may never want to meet. They may really just want to have a correspondence. Hey, if you want a pen pal, that’s fine. But I say have a couple of exchanges by email, have a phone call. And then if that seems promising, have a coffee date. And I would say you can do it within a week, certainly within two weeks, unless there’s some particular reason not to. But I say move it fast, and then decide yes or no.


So move it fast to get to the first in-person meeting.


LAURA STASSI: But then I think this is where a lot of people get tripped up, how much; how fast is too fast. You don’t want to look needy or overly eager. But you don’t want to play games. I’m hoping at this point, nobody’s playing games.


I think if you really connect with somebody, and you’re talking on a real level, and you have things in common. Most of the people I talked to said by the end of the date, they didn’t want it to end. They knew they wanted to see this person again. And nobody was playing games about it. Either one could say you know, I’m enjoying myself so much. I’d love to see you again. And the other person would say, I’m gonna be out of town next week. But how about, you know, I call you or we make a date. And it happened naturally.

I think you do have to be careful, though, of within the first few weeks seeing each other three times a week and talking every day. Because that generates a lot of fantasy and doesn’t give you time to reflect on, what have I learned about this person? What’s great about him or her and what gives me pause? In order to — you need to let some things sink in and not just be caught up in the frenzy. Oh, I’m in love. I’m in love. Because you feel that at any age. You know, chemistry is mysterious. So the most important thing for me is the relationship, and I have found that if I don’t like the guy’s haircut or glasses or he needs to take off a couple pounds or his clothes are no good, that can be changed easily.


Although, although we don’t want anybody, man or woman, going into a relationship thinking, I can change this person.


No, no, no, no, but the superficial things. You know, like when I first met Michael I found him very attractive, but he had his hair pulled back in a ponytail. And I’ve always hated ponytails on guys. And I said to him one day, are you committed to this ponytail as a sign of your identity? He said, no, I’ll cut it off.

I’m very short. And I’m not a knockout beauty. I walk into a room, like at a party and people look right over me. I am so much better one on one. So online totally works for me. And I very quickly learned how to make it work better for me, and I recommend it heartily.


I think Francine makes online dating sound like a fun adventure. And speaking of online, Francine told me she’s never used a dating app, because she has concerns they might promote rushed decisions based mainly on photos. I wonder if there actually is a difference between sites and apps? I put that question to a dating coach.


I don’t like the word coach.


AARON: I really view myself as someone who comes into your life. And I look at a system, which is your dating and relationships and romance. And oftentimes, your dating applications or dating sites. And I make recommendations for improvement, which to me feels like consulting.


That’s Aaron Hunt. He’s a dating consultant, apologies. Our conversation is next.

LAURA STASSI: Aaron Hunt is a dating consultant based in Washington, D.C. He helps guide people through making love connections. That includes using dating apps and dating sites.

AARON: 11:55

So I think that a mix of both can be really good. And so usually I just talk to people to see what they’re most comfortable with. You know, if I can teach my 99-year-old grandfather how to use his computer, I feel like I can teach anyone how to, you know, use an application, I will say, dating applications, at first can seem really, really overwhelming. However, a lot of them are pretty similar. So once you kind of learn one, you kind of get the gist of it. And they’re not too different from dating websites.

And so sometimes when people are really nervous about maybe making that switch from a website to an application, I will suggest maybe a site like OK Cupid, which has both an online application that you can use on your computer, you can log into it, and they also have a mobile app, so you can use it on your phone. And so kind of getting used to being able to interact with like that dating website, but through the medium that you feel most comfortable with. And then oftentimes that can help people to feel kind of more comfortable with using their phone for dating.


So some of them are both and some of them are just apps.


LAURA STASSI: I think though, just talking anecdotally, and again, I don’t have studies in front of me, but that some people are really nervous, older people — some older people are really nervous about using their phones, because it feels like it’s more of a rushed decision you’re making whereas with the laptop or a computer, you can sit down and have a glass of wine or a cup of coffee and kind of really take your time reading the profiles — where that might be a little trickier for older people on the phone.

AARON: 13:42

Yeah, so I would say it depends on which application you’re using. So you know, if you are on something like Tinder, where it is primarily photo based, and not a lot of writing space for a bio, it might feel like that. But you know, in the same way that you can use like an OK Cupid or on the computer, it’s the same exact profiles on the phone. And so I think that that might be more of a mindset.

And that’s one of the perks of hiring, you know, a dating consultant with a background in psychology is, I can sometimes catch those maybe biases that people have. And we can talk about, well, what is it that feels different about, you know, using a phone than using your computer? But that’s also why for some people who aren’t super comfortable with using a mobile application, I like those sites that offer both. And you can try out both and see how it feels. But when I’m dating, I also do sit down with a glass of wine and my cell phone and look through profiles. So yeah, I think you know, it can work for either way.

But I think it is mostly about comfort, and I think something I tell all of my clients — and I think I often need to maybe remind my older clients a little more — is that dating should be fun. And so if you’re not having fun, you’re not doing it right. So yeah, definitely, we should have a chat about what is not feeling so fun and how we can make it more fun. And what’s getting in the way of making it feel fun?

And so I love what you said about, you know, sitting down with a glass of wine, and I’m going to read through some profiles, and you know, have fun with it. You know, if you have some girlfriends that are also single, make a night of it, you know? Get some — get out that pint of ice cream, grab that red wine, sit down together, laugh at profiles. I don’t want to say, you know, if you don’t laugh, you’ll cry. But sometimes it can feel that way with online dating. And so really, the spirit that you’re approaching it with, and also it’s okay, if you need to take a break. Or, if you feel you can only look at a couple profiles in one setting, that’s fine. It’s about finding out what works best for you. We certainly don’t want you to be looking through profiles with a chip on your shoulder or feeling fatigued or feeling very annoyed.


I do encourage older clients no matter their gender and sexuality to be more assertive, and to — if it is an expectation that they’d like to be pursued. That’s an expectation that needs to be set and communicated. I don’t recommend that you put that in a profile. Normally, once I say that people are like, Oh, wow, it sounds pretty terrible for me to say that someone else needs to put in all the work up front, doesn’t it? And I’m like, yes. But sometimes, that’s what people want. And it is okay. And many older adult adults still are a little more traditional in that way. And so that dynamic might happen on its own. And that’s okay.

But I do encourage people to be more assertive, I definitely have worked with older women who were like, well, I can’t send the like, I can’t make the first move. And I’m like, don’t think of sending a like as making the first move. Think of it, as you know, back in the day, when you were at a party and you lock eyes with someone and you smile. You can do that. And that’s what sending a like is. It’s a way of saying, I see you, I like what I see. Or, I’m interested in what I see. Or you know, you can approach it. I certainly encourage anyone to be sending those likes, because how else are the men that you like going to find you or know that you like them, if you’re not going to send likes?

I always say if someone has a profile, and you are intrigued by something, does not hurt to have a conversation with that person. Again, if you have the time and energy, because matching with someone on a dating app, having a conversation with them on a dating app, does not mean you need to go out with them. And it’s certainly it’s not a marriage proposal. It’s okay just to have a conversation with someone and decide that you’re not interested. But part of the fun of dating —

And I think you know, a spark can be very fun. But for me, what’s more fun is finding someone and learning about them. And finding all these ways that were more compatible, are finding out that they’re such an interesting person or finding out how lovely they are. And it’s something that you wouldn’t have known just from their profile. And that, to me is the fun part of dating — is not every firework but that discovery and learning about someone, and getting to know different people, and learning what makes them tick and the things that they love and the things that they care about and what we have in common and having those types of conversations. And you can’t have those unless you talk to people


I’ve had such the bad attitude. I’m now realizing,

ARON: 18:52

Well, I do free consultations.


I think we’ve just had one.


LAURA STASSI: So the way Aaron describes it, sounds like online dating can be a thoughtful process, regardless of the specific technology that’s used. Thoughtful process — that can be a whole lot of work. And there are no guarantees of favorable results.

CLAIRE: 19:19

Tried online, didn’t work out. Because what happens, people you know, at least the people that I met, they sounded great online. But when you meet them, they’re very different. They weren’t the people that they represented in their profiles, and in the correspondence.


That’s Claire. She’s in her 60s, has never been married. No kids. And like a lot of us, Claire’s tried online dating. She made a few connections, had some dates, but overall she found the experience disappointing.

CLAIRE: 19:50

It was just like, if this is one that’s out there. I’m happy by myself. I just got to the point where I just got tired. I didn’t really date for probably over 10 years.


So Claire got offline, but she didn’t give up for good. In late 2019, she got online again. This time, her profile caught the attention of a retired teacher. His name is Jim. He’s a few years older than Claire, and he’s been married and divorced twice to the same woman.

JIM: 20:20

I let my schoolwork world take over. I took the good things for granted, let the negative things get larger than they needed to be. In the meantime, she had found some solace or some connections with a — I’ll call it a religious group. The world was black and white. I’m more like an open-minded type. We were unable to find what I thought was a good compromise.


After that second split, Jim decided he was done with romantic love. But then he had a health scare. And after making a full recovery, Jim changed his mind.

JIM: 21:00

In a lot of ways, I woke up and said, this thing we call life is just a moment by moment gift.  And I thought, well, I can be safe and never try to get to know anyone again, which I was — was slash am –very good at. Or I could take a chance and try to get to know someone. And that involves some messiness and some pain, but I have to make, have to make a choice.


When you got online, did you pick like one site or three sites or …

JIM: 21:37

One. I had sort of a mental list. There’s — not in order. They have to be positive and have a sense of humor. I wanted to someone that had a wider scope, wider perspective than other people.

LAURA STASSI: Who reached out to whom first?

JIM: I think I reached out to Claire. She seemed like an interesting person in that she was helping out with a local theater group. And she was working with diversity and inclusion. I didn’t know what that was at all, had to look it up. Thought, well, if she can do that she’s skillful with people, has a lot of emotional intelligence.


And what was it about his profile that struck you?

CLAIRE: 22:25

You know, I said, I’m an extroverted introvert and he goes, I’m an introverted extrovert. Or vice versa, whatever it was, the fact he actually read my profile, and responded to the profile, which — because words matter, and you know, to me, and really paying attention. So I was interested in meeting him.


And you’re how many miles apart?

JIM: 22:48


LAURA STASSI: Sixty-two. So did that bother either one of you at first?

CLAIRE 22:52

I had no idea where he lived. Just like, I’d never heard that … I had to look it up on Google Maps.


So you guys talked back and forth?

CLAIRE: 23:02

Actually, no, we actually only emailed each other.


How long did that go on before you decided, let’s meet in person?

JIM: 23:10

Two weeks?

CLAIRE: Yeah, a couple weeks. He reached out to me on Christmas Eve.


Now was that kind of — so there’s two schools of thought on that. One is oh, he reached out on Christmas Eve! Or, oh, this is what he’s doing on Christmas Eve?

CLAIRE: 23:25

No, it didn’t really bother me either way.


And were you thinking I’m so sad, I’m gonna get online … or was it like…

JIM: Oh, no.

LAURA STASSI: You see I’m trying to rile you up.

CLAIRE: 23:37

We’re very independent counter spinners. We’re not the usual.

JIM: 23:49

I really messed up our first meeting. I didn’t write the time down …

CLAIRE: Even though you picked it.

JIM: Yeah. I said, let’s meet on such a such a day at such and such a time. But I relied on my memory. I waited about 45 minutes. And then it dawned on me, oh, I’m late, and she already came and left.


Oh, is that what happened?

CLAIRE: 24:12

No. He actually had a time after — so I arrived 15 minutes after he left, being early for the time we’re supposed to meet — in the rain.

JIM: 24:26

So I drive back to Maryland and get online and apologize for being late, when I had left 15 minutes before we were supposed to meet.

CLAIRE: 24:36

And I sent him an email saying, I’ve waited here for 45 minutes, and I hope you have a great evening.


But there was a second date.

JIM: 24:45

Well, her heart – I was almost said it was too large, but it was large enough that she gave me another chance. I mean, I’m guessing a week — like a week later, and I sent her the address. I was there early. And I put it in my Google Calendar, and I wrote it down.

CLAIRE: 25:05

It was nice. He gave me gave me some flowers and, and a book.


CLAIRE: Yeah, a book on Chinese immigrants.


Oh, wow. You’re a present kind of a guy on the first date — or was it an apology?

CLAIRE: It was an apology.

JIM: 25:23

We talked for at least an hour, I think.

CLAIRE: 25:26

Yeah, we’d seen each other a couple of times. And then, and then I met him on Valentine’s Day. And then he asked me to be his Valentine. And I thought it was so cute because you wanted to sit next to me. Oh, he wants to be close to me. It’s like, no, I don’t want to have eye contact with you.



JIM: I talk better when I’m not like, having …


Eye contact. So the lockdown happens. Did y’all have a conversation, okay, what are we going to do?

CLAIRE: Not really. I mean, he, you invited me up, you said you would be safer if you came up here.

JIM: 25:57

It was like, we could spend six hours driving and meet at a park and ride and get a total of 45 minutes’ conversation. Or we could like, get a year’s worth of conversation in a month. It made me nervous, but the potential positive outweighed the potential negative.

CLAIRE: 26:19

It was like, you know, oh, you know, I’m gonna get to know him really well. And well, it’s either going to work or it’s not going to work. But I felt comfortable because we had already seen each other a number of times.

JIM: 26:31

It’s like when you’re bowling, you hit like three strikes in a row. It’s like, wait a minute, I don’t know what I’m doing. But I’m getting strikes. So we’re getting along. I don’t know why or how but we seem to be getting along. And we laugh a lot. But that’s because of who she is.


I don’t know. I feel like you are selling yourself short.


JIM: 26:50

Okay. Thank you.

CLAIRE: I would agree. I mean, all my friends are like — you know, even my sister’s like — he’s a keeper.


Jim and Claire lived together at Jim’s house for six weeks. And then Claire returned to her own home, and they continued to be a committed romantic couple. They live happily apart, and they happily see each other as often as they can. And in February, they marked their second anniversary as Valentines.

You know, I am all for meet-cute romances. But stories like Jim and Claire’s make me understand why so many people turn to technology to find love. I mean, Jim and Claire probably never would have met in real life had it not been for online dating. They each took a leap of faith, and they made a good effort to get to know each other. And when the first date didn’t go as planned, they took it in stride and gave it a second chance.

And really, whether it’s a dating site, or a dating app, or which specific site or app that’s chosen, isn’t that what we all should be doing on the journey to find love? Take a leap of faith. Make a good effort to get to know someone. And before deciding it’s time to move on, give another chance.

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