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Episode Transcript: Chatting Up Strangers

This is Dating While Gray: The Grown-up’s Guide to Love, Sex, and Relationships. I'm Laura Stassi, and you might think that I have no trouble approaching anyone to talk about anything.

LAURA: Is sexual intimacy important to you?

INTERVIEWEE 1: Yeah, I think it's the wrong question.

LAURA:  00:26
I would hope that there's no man in my life who can't remember, like how he met me, or what made him you know, this spark.

INTERVIEWEE 2: That’s strike one. Keep pitching.

INTERVIEWEE 3: Turn that microphone off.

LAURA: But you would be wrong. When it comes to my personal life. I have trouble Chatting Up Strangers.

Here's an example of why I need help with my personal conversational skills. Back in the fall, I went to my nephew's wedding in the Chicago suburb of Oak Park. That Saturday morning was sunny, in the 50s, perfect jogging weather. So I laced up my shoes and made a four-mile loop past cute little shops and down wide, tree-lined streets with Prairie-style homes. When I finished my run in front of a bakery, I was feeling good.

I went inside to get a cup of coffee to take back to my hotel room. And as I'm waiting, I glance out the picture window and see a group of men on bicycles. They come to a stop at the sidewalk cafe tables right out front. And as they take off their helmets, I can see they're older.

They have gray hair. I have gray hair. They’re wearing workout clothes. I am too. Endorphins are flowing … it feels like an opportunity to meet new people has just presented itself. I could ask them to recommend a different route for my run tomorrow. Or do they have any suggestions about what I should see or do before I leave town? I couldn't even mention I have a podcast. And it's about older people and dating, and what do they think of that?

So guess what I said to them? Yep, nothing. I got my coffee and left. I didn't even try to catch someone's eye and smile on my way out. I got nervous. I'm not the only one that’s let an opportunity pass them by.

SHELLY: 02:29
I was just sort of standing there. And she slowly turned around and looked back at me from down the hill and looked up, and she just looked kind of disappointed -- is the feeling I got from the look, like she's still there. Like, why didn't we say more something was the feeling I got from that look. And I'm like, what do I do now? Because I wanted to run down the street and say Hi, my name’s Shelly. Like, here's my number. But I didn't because I just froze up.

LAURA:  02:57
Shelly is 50 and was married and divorced twice before coming out. She says she sometimes has trouble talking to strangers. But when she feels a romantic spark, she really chokes. We chatted recently; you may hear some bracelet noises in the background. And she started by reading part of the email she sent me about an encounter that haunts her.

SHELLY: 03:19
So last spring, I was out walking in an unfamiliar neighborhood about a quarter mile from my home. A woman went by me on rollerblades. She was athletic and pretty and had a long black braid down her back. Then she came by me again but actually stopped on the road next to me this time. We started talking. Now, I tend towards shyness and being socially awkward at times, especially if I'm taken by surprise. And talking to this woman I just noticed certainly made me nervous and shy.

Anyway, we managed to talk about the neighborhood being full of cul de sacs and new to both of us, and about the weather. She told me the name of what I guessed was her neighborhood, but I hadn't heard of it before and didn't know what to say. She nodded and then just gave up on trying to talk with me. We quietly muttered goodbye and she rolled on down the street. Then she turned around and looked back at me. It was like she was moving in slow motion. She had a look of disappointment on her face. Yet I still did nothing. I searched for her all around the neighborhoods for months after this. I even looked up the name of where she said she lived and learned it's an apartment complex just down the road for me. I was so desperate to find her again. I even called the apartment complex and asked if they could help me connect with her. No luck. I started feeling extra lonely and sad at my lost opportunity.

I felt so weird. I'm like they, probably think I'm a stalker. And this is terrible.

LAURA:  04:46
How -- what did you say, a woman with a long black braid on rollerblades? How did you explain?

SHELLY: 04:54
Yeah, I kind of told the story like we met in this neighborhood going for a walk, and she seemed really nice, and it would just be fun to walk with her again. And yeah, that's all I could describe her and like, I don't even know her name.

LAURA:  05:07
Sometimes in those moments that, you know, there's a lot of regret, I think, a lot of people experience. Like, looking back thinking, why didn't I put myself out there? Who knows what would have happened? I mean, maybe she was not lesbian. Maybe she was married. But just it could have been just a connection that could have enhanced your life.

SHELLY: Yeah. Yeah, exactly.

LAURA:  05:34
So what were some of your regrets? You know, it sounds like you kind of mulled over this a lot after it ended. And looking back, what would you have done differently?

SHELLY: 05:46
That's a good question. Well, I think it'd be great if I could remember, like, we're just people and it doesn't -- the outcome doesn't matter. It’d just be so nice to just be calm and friendly and say, hey, you know, my name is Shelly, you know. What's, what's your name? I mean, just the basic like, how do you meet a new person and strike up a conversation, have a friend rather than have that whole -- all that worry behind it of wishing that there would be a certain outcome? I think that's the biggest thing. Just let go about possible outcomes and worries about that. And just enjoy the moment talking with somebody.

LAURA:  06:25
Yeah. Now, if you knew -- like if it had been a man, so clearly, you weren't interested in a man as a romantic partner. But let's say there was something about this man that seemed, I don't know, interesting or intriguing to you. Do you think you would have struck up a conversation with him?

SHELLY: 06:44
Yeah, I could see easily just chatting like, yeah, men are fun to talk to.

LAURA:  I totally agree.

SHELLY: 06:50
I mean, I have a lot of men friends. I wish I had more actually, because I've always enjoyed hanging out with guys. And I used to play ultimate Frisbee. And so I had a whole bunch of guy friends and we had so much fun together. Yeah, it would be really fun to talk. And then I also know like, in my back pocket like, well, if they asked me out or something, I can very easily say, well, I'm gay, but it'd be fun to hang out and be friends. So it doesn't make me nervous to talk to guys ever anymore.

How do I, like -- how do I quiet the self-talk of all that worry. And all those what ifs this and what if that, to just be able to talk to someone that is another single lesbian that maybe someday I could date? Like, I want to say things that it wouldn't come across as desperate or like, you know, too eager, overly eager, I guess is -- I worry about being feeling overly eager and it coming across and then it making someone not want to talk to me.

LAURA:  07:58
Oh, it's too bad Shelly couldn't keep that serendipitous conversation going. But I don't think this is unusual. Sometimes it happens even if you've exchanged names with someone and planned an actual date.

ALICE: 08:10
And I think for a while I stopped listening too. I like kind of, you know, after -- well, I you know, I tuned him out.

LAURA: So he was talking.

ALICE: Yeah.

LAURA: It wasn't like he was silent.

ALICE: I think I may have been thinking about my to-do list for Saturday.

LAURA:  08:27
We'll hear more, after the break.


LAURA: A woman we're calling Alice is in her early 60s and has been divorced and then widowed. Earlier this year, she made a promise to herself to be more open to new experiences. So when she was scrolling through social media one day and came across a single friend of a friend, she checked him out and then reached out. He responded, they texted back and forth a few times. And then he asked her out. Sounds promising, right? But when they met for their date, Alice discovered their conversation did not flow.

ALICE: 09:52
Well I mean, I think at first you know, just getting to know each other and um you know just chit-chatty. But it seemed like -- how do I describe this? I sensed pretty early that it was like kind of we weren't -- we were disconnected, not engaged. Because when you're engaged in a conversation, it's like tit for tat, right? You know, you talk about something, they engage, they share something. But it was like engaging, and then silence and then change the topic. It was like we were on different channels.

LAURA:  10:26
I mean, so you're saying, like, let's just pick a random topic. So you're saying, like, this is beautiful weather for the beach. I love the beach, you know, what's your favorite beach? And he'd say, Ocracoke. I like to eat fish. I mean, was it like that?

ALICE: 10:42
It was more like, like, what's your favorite beach? And then talking about, like, a whole nother subject about like a work travel trip or something like that. So it was like we weren't -- we were on different frequencies.

LAURA: Yeah.

ALICE: And so I kept finding that it was difficult to sort of be engaged, because you know, that that is how when you talk with someone and you're comfortable, it's like you're engaging and even like when your body your nonverbals, right? You know, you're leaning forward, they're leaning forward, you're connecting. And he also didn't, he wasn't giving me eye contact, either. So it was just uncomfortable. And then what I did was, I just wanted to fill the space up, right? Or sometimes I didn't say anything, and there was just quiet, that awkward sort of quietness that is a really pretty uncomfortable when you're trying to get to know someone.

LAURA: 11:36
So it wasn't a comfortable, let's sit in our silence.

ALICE: No, not really.

LAURA: Do you think he sensed that it was uncomfortable or awkward?

ALICE: No, no.

LAURA: Okay. This was just maybe his way of communicating?

ALICE: 11:54
Yeah, I mean, now that I think about it you're probably right. I mean, it was just, you know, we all have our own ways. And, and maybe I'm thinking about for myself, maybe, you know, my experience with dating had been kind of limited for a while, right. And I only knew what I knew. And so maybe it takes time to sort of get used to someone else's style. And to be, you know, maybe not so judgey about it.

LAURA:  12:22
I like that you're saying that. But I also hear and like what you're saying about just trying to fill the space because I'm totally like that. It's like, this is awkward. Okay, or I also judge immediately. This isn't going anywhere. What does it matter what we talk about? But so when you say you were trying to fill the space, was it just sort of like a nervous chatter? Or were you trying to draw him out and to sort of, I guess, re-engage?

ALICE: 12:49
Oh, yeah, a little nervous chatter and little engage. But I think the more I think -- I feel like the harder I tried, like, the worse that went. And I think for a while I stopped listening too. I like, kind of, you know, after a while I you know, I tuned him out.

LAURA: So he was talking.

ALICE: Yeah.

LAURA: It wasn't like he was silent.

ALICE: I think I was even thinking about my to-do list for Saturday.


LAURA: We're not laughing at anybody. We're all laughing in just recognition of what sounds like it was an awkward encounter.

ALICE: 13:21
And it could have been for him too, like, when is she going to shut up? And like, why all the questions? I mean, maybe it's about like, sometimes when we connect with someone, it is that communication style and you're vibing-- you know what I mean? And some people are just really good at it.

LAURA:  13:41
I'm wondering if there's anything this individual could have done or been that would have motivated you to attempt to engage more -- you know, maybe switch up how you were responding, what kind of questions you were asking him? I mean, what are your thoughts on that?

ALICE: 13:58
I just think if we had connected, because, I mean, we connect with people physically too, but we also connect to them, you know, through our communication styles. And I think -- I don't know. I mean, I do agree, we're, we're onions, you’ve got to peel back the layers. And the more that you get to know someone and all of their layers, they do become more attractive to you physically, you know. But also there are signs when you realize like that it's just, you know, not a good fit. Or maybe I quit too soon and don't peel off enough layers, which is why I'm still single.

LAURA:  14:39
Well, I admire you for reaching out in the first place to him because I think a lot of us -- I know I personally sometimes feel like okay, I'm gonna be judged.

ALICE: 14:49
Yeah. Or like you're kind of creepy or whatever. Stalker, stalker! Here's the thing though, is we can interpret all kinds of other people's, like thoughts and behaviors and all of those things. But we’ve got to ask the questions, right? What does that mean for them? So, which is why I think it's so important to have good communication. When you go on a date with someone that you don't know, you're really vulnerable. Right? And then they are asking you personal questions, and you don't know them that well. And so it's hard to put yourself in a place where you're open and vulnerable, because you could get hurt. Your feelings could get hurt, right? It's risky.

LAURA:  15:39
Alice and her date? One and done. And I think there's a lesson in there somewhere about texting as a form of communication, though Alice doesn't regret the date.

You know, I like what Alice said about vibing with someone, it feels more significant than a spark, and vibing with someone requires communicating with them.

I can meet anybody, I can walk into a room and have 30 people and I'll know 20 of them by the end of that, and they'll come away with a really good impression of me. And it won't be me hustling to network them. It'll be me connecting with them.

LAURA:  16:14
Meet advertising and marketing guru Fred Joyal. He describes himself as a one-time extreme introvert who learned how to put himself out there. It led to business success and his latest book, “Superbold: From Under-Confident to Charismatic in 90 Days.”

FRED: 16:31
I never approach anyone with an agenda, with a desired outcome, except to meet them to learn who they are.

LAURA:  16:40
I would not consider myself a shy person. But I have had situations where I just freeze when given a potential opportunity to meet people. And I know from emails I've received that that's happened to other people as well. So what are we telling ourselves in these moments of hesitation, that are so destructive?

FRED: 17:05
It's a really simple, loud message, I am not worthy. But we, we have decided from all of our other interactions in life and childhood and parental messaging. And in some ways, it's, it's kind of ridiculous, because all you had to do was walk up and say, Hi, I'm Laura, I'd really love to meet you. How many people are gonna say, Get out of my face. And if they do, they're a disturbed person that you don't want to know, or you they're disturbed just in that moment, and you don't, it's not you. That's not a natural human response to barf rejection on someone. So that's their problem. Whatever is going on with them is not about you, it's all going on with them.

And everyone doesn't have to love you. That's, that's sort of an impossible goal in life. But some people are going to find you interesting. The way they're going to find you interesting is by you focusing on them, not coming at them with all of your stuff, whatever it is

LAURA:  18:18
Coming to somebody with an agenda as opposed to coming to someone with just the pleasure of wanting to meet them -- I think that's probably what holds me back, and what holds other people back sometimes is we have a supposed agenda like, oh, I wonder if any of these men are available and interested in going out with me? As opposed to, here are some interesting looking strangers.

FRED: 18:43
The reason you're having trouble also talking to them is you don't know what else you're gonna say. You feel like you have to offer something. Maybe you have feel like you have to be witty or clever, or interesting. You don't. All you have to do is ask questions, open-ended questions. Wow, these bikes look really expensive. How would you know? And they look like they weigh nothing. What do these bikes weigh? Just start asking. They, they ride bikes. They're going to talk about their bikes, and then you can say wow, the seats look really uncomfortable. Now, you get your next question. Can you ride those things for three hours? Okay, so your prostate…

LAURA:  19:33
I mean, okay, talking about expensive and physical discomfort. Those don't sound like good conversation starters to me. Am I wrong?

FRED: 19:45
Well, except that to somebody who rides a bike, they want to talk about it. Some of these bikes are $10,000 and they weigh like 15 pounds. And so anybody who spent $10,000 on a bike wants to talk about the bike. And anybody who’s sat on one of those seats, wants to talk about how uncomfortable it is. You could say, look, doesn't that bother your prostate? And they will just laugh and say, well, you know, I do get up to pee like four times at night because of it, or something.


FRED: At some point, you can say, one of the things I do is I have a podcast on dating, while people are gray. What? Tell me about that! And then you don't. You say -- you come back with a question. You go, yeah, I can tell you about it. But, uh, you know, are you single? Are you dating? How has that been for you? What -- I'm really interested in your experience, as somebody who's, you know, over 50 and, and out in the dating world, instead of monologuing. That's one of the big things that we do when we finally meet somebody. We begin this enormous monologue.

LAURA: Yeah.

FRED: And, and it doesn't work. Because you can't, there's no moment where you can actually gauge whether it's interesting or not. You're just rolling on; you have all of this stuff to say.

LAURA:  21:15
So we see somebody that we think, okay, let's strike up a conversation. But we don't approach anybody with an agenda. We just approach them with the idea of, I would like to meet this person. We're kind of in a similar circumstance, whether we just happen to be sharing the same zip code at the moment. So we approach them that way. And then once we approach them, you said, we're asking questions, we're not monologuing. And so asking questions based on the situation, or is it something like, what do you think about the weather?

FRED: 21:56
I don’t like “how is the weather?” as a question. it's like, it's basically saying how you doing? it's a non- conversation, I want to, I want to compliment them and ask them a question. And you say, wow, tell me more. Three magic words -- tell me more about that.

LAURA:  22:18
I like that. Three magic words: Tell me more.

FRED: 22:21
That in your head, that's your driving motivation. Tell me more -- not, I want to tell you about me. They will be interested in you because you're so interested in them. They will eventually ask you something. And you're going to answer very quickly, and then go back to interviewing them, finding out more about them.

LAURA:  22:46
Is there something that we can say to ourselves that will motivate us to go talk to somebody or to approach someone?

FRED: 22:54
The mantra that I use myself and I recommend to everyone is, I belong everywhere. Wherever I am, I belong there. You know why? Because I'm a human being just like everybody else.

LAURA:  23:11
I had a lightbulb moment when Fred talked about approaching strangers without having any agenda other than getting to know another human being. I think I used to do this before I got divorced. Now, I can't help but prejudge: Is this person date material or podcast material? Feels like I've been missing out on potentially enriching experiences with people who won't fall into either category.

So I'm going to change that by vowing to talk to the next stranger I encounter. And I will strive to keep the conversation going by using the three magic words. Tell me more -- though, if you're a man with a bicycle, please don't tell me more -- please don't tell me anything -- about your prostate. Sorry, Fred, but I'm not going to be taking that suggestion.


Dating While Gray is produced in partnership with WUNC, North Carolina Public Radio. Our producer is Morgan Givens. Charlie Shelton-Ormond is our editor. Lindsay Foster Thomas is WUNC’s director of content, and Jenni Lawson is our audio engineer. Katy Barron edits our e-newsletter.

I’m Laura Stassi. If you have a question or a comment, e-mail And now you can also leave me a voicemail. Go to and at the top right, click on “Talk to Us.” I'd love to hear from you. And thanks for listening