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Speed Dating While Gray: Tell Me About It LAURA STASSI Laura Stassi here, and welcome to Speed Dating While Gray. They’re episodes under 15 minutes long, offering bite-sized morsels of your favorite topics. We’ll be dropping them every other week … and I’m thrilled to kick it all off with my conversation with Meredith Goldstein. She’s an advice columnist for the Boston Globe, and host of the podcast Love Letters. You’ll hear one of my favorite Love Letters episodes directly after this episode. So the Love Letters tag line is where real people tell stories about dating, relationships, and falling in love. If that sounds familiar, it’s because Meredith is one of my role models. I found out about her back in 2018. I’d just been selected for an incubation program to develop my Dating While Gray writing project into a podcast. And one of our first assignments, was to find an aspirational show. Meredith had only recently launched the Love Letters podcast. But she’d been writing the advice column for over a decade. MEREDITH GOLDSTEIN For context, I'm turning 47 this year. So it's amazing the confidence I had at 31 to be like, I know how to tell people about their 30-year marriages. I did think I had some expertise. I knew what I didn't know, which I think was important. I was often saying, you know what, I've never had kids and I still am not a parent, right? I had grown up in a household with a divorcing mother. And was probably maybe too involved in that journey through discussion. And I was constantly thinking about who my sister was dating, who my mother was dating, who my friends were dating, who they weren't dating. And I felt it very comfortable to be a voyeur and not date anybody at all really for most of that time. And I felt like it was really an anthropology project of sorts to see how all these different generations of people in my life were experiencing love. LAURA STASSI At the same time, and we've talked about it a little bit on Dating While Gray, it must have been very awkward, difficult, or was it -- having parents who were divorcing. MEREDITH GOLDSTEIN: Well, it's interesting. As a child of divorce, you have all these judgments you make of like, here's how they're doing it wrong. Here's how my parents are doing it wrong. And then you become the age they were when they got divorced. And it gives you a lot more empathy. Like, of course they were doing it wrong. They were in their early 40s. Divorce is hard and there's no way around it, but staying married would have been a lot worse for all of us. So I am very grateful that my mother in particular, you know, some may say there was an oversharing in my household, but her ability to be transparent with me really made me look at everybody like people. Her willingness to show me what she didn't know and to ask me for advice as like a teenager and be like, does this seem weird to you? And I'd be like, it does seem weird. We were collectively clueless and figuring it out together. LAURA STASSI I'm wondering about dating when you're younger or dating when you're, I guess, more experienced with dating versus dating when you're older or dating when you really have no experience. Like, for example, dating apps, which I finally gotten comfortable calling them dating apps as opposed to online dating. MEREDITH GOLDSTEIN Online dating? Yeah, I do it too. LAURA STASSI Yeah, I'm not ready to proclaim them, quote, the best way to meet a romantic partner for people over 50, even though a lot of dating coaches and relationship experts will tell you, oh, it's the best way. MEREDITH GOLDSTEIN I mean, I'm not sure dating apps ever feel like the best way to date for anybody at any age because when you're in them, you're like, oh, this is a little bit terrible. And to be 25 and experiencing that can be overwhelming and unpleasant. And to be 70 and experiencing that can be deeply unpleasant. I think they can work for both ages. I think it's also important to put them in context, which is that we overuse them. We are on them for too many hours. We are like digging for some sort of buried treasure sometimes. And it can't take the place of real life, of community, of connections. You mentioned calling them apps as opposed to online dating, which I have trouble with that too. Still call it. It's like that says to me, oh, well, you're used to them now. And I think as you get used to them, you figure out how they're best for you, which are the platforms that your eyes like looking at. You begin to realize when to forgive that someone doesn't know how to take a good photo of themselves. You begin to notice when someone takes a photo that is too good of themselves. And you get your own habits of what you accept. And there are other ways. So I love setups. I love meeting in real life, as they say, but I think that there are a lot of people who want partners, and they are on these apps. LAURA STASSI So I know that in 2018, you had a romance with somebody you met at work, which used to be a very common way of meeting somebody. So, okay, without jumping to the end, you are in a relationship now, yes? MEREDITH GOLDSTEIN I am, and I do not work with him, thank goodness. I met him on an app while it was lockdown. So I was on this app with a friend who was going through a relationship breakup and so it was more for moral support that I was on the app. I was like, he was like, if I can do it, you have to do it with me. And I would turn it on for like seven minutes at a time. LAURA STASSI: Oh, why seven? MEREDITH GOLDSTEIN I don't know, it was like random, but like minutes. Like I wasn't just like fully on there. It was like, it felt like an eclipse, right? Like, oh, here are the minutes. I would do this with him. It was like testing the waters. But I also had the luxury of saying, I'm not gonna meet any of these people in person. It is a lockdown. I'm not leaving my house. This is just for sport. And this person and I like, connected, kept in touch, eventually took long walks together. We had a very like Regency Romance style courtship for that reason. Lots of, lots of walking, burning a lot of calories. And I wasn't even, I thought maybe this is my weird pandemic friend that I've made. And when things opened up and we were vaccinated, I was like, oh wait, no, I like him. So it is interesting to me that like that era, I think slowed everybody down a little bit. And we always talk about how, like, if the world had been sped up, would we have had time to truly connect? LAURA STASSI Interesting. MEREDITH GOLDSTEIN We are two people over 40 who, he's divorced, so the last time he dated, there were less rules. And I think it's also very difficult when you're older, over a certain age or after a place in life to be like, oh, I like things how I like them. I get a lot of letters from people over 60, I would say, and I think that's because of the Globe's demographic. And that's one of the biggest things is like, I would really like a partner, but like if you move where I put my napkins, I will lose my mind. And how do we do that? How do we accept partnership that is new without everything becoming chaos in our lives? LAURA STASSI I've had a lot of women tell me lately that they have reclaimed, they've used the expression, reclaimed their feminine energy. And what I think I'm hearing them say is, I am a feminist. But I want to be wooed or I want to revert to some of those traditional dating rules or standards where the man is supposed to do the pursuing and if he doesn't call by the blah blah. And so what are your feelings about these rules? Listen, do whatever you want and have the rules you want to have. But I think maybe what you're hearing and what I'm hearing is a lot of people are tired and have not been romanced in a long time. LAURA STASSI Oh, can you say that again? I think that’s important. MEREDITH GOLDSTEIN: A lot of people are very tired and have not been romanced in a long time. LAURA STASSI: Yes. MEREDITH GOLDSTEIN And that is rough. And if you want that, I'm all in on that. Now, once you get to this granular level of, well, that means this person calls first and this person responds second, it can get a little tricky. But sometimes people are shy, and you have to message them first. I mean, Bumble and heterosexual relationships, like sets it up that way. But give someone the chance to be romantic in the way that they are. Give someone the chance to get to know you so that they can cater that romance to who you are. I get it. I think it's great if you feel like reclaiming your feminine energy and accepting that kind of showing of affection. I just would say it's a two-way street for that. And it may look different and it may look better. LAURA STASSI May I ask, are you living with your partner? MEREDITH GOLDSTEIN Uh, not today. Ask again next week. LAURA STASSI: Oh! Is this breaking news? MEREDITH GOLDSTEIN Maybe. I mean, we're figuring this out. Again, figuring it out. But it is a constant discussion, I will say that. And you're hitting on a thing, right? Which is that, like, we are two people now who've lived alone for some years. And, you know, you have to ask yourself, like, is this why it works? Because there's, like, room to miss someone? I have never been married and I've never had a 30-year relationship. And I go out of my way to truly imagine what it would be like to start something new, especially when you didn't want to, especially if the end of that relationship was not your choice. And I can be super pep talky and hopeful and say the world is different and think about what it would be like to be with someone who chooses you, or think about what it would be like to be alone and have a bunch of friends and do cool stuff and like be like a character on TV who like, you know, is aspirational. But I know that especially in the beginning as you set up new routines, it doesn't feel like that. So I do know that, but that's one of the moments where I'm like, oh, I have to remember that I spent a lot of years mastering being solo. And I got real good at it, too good at it, if I am to be honest. And I also had a commenter say to me, you know, Meredith, often you will say, lean on your community of friends. And not all of us have that. Not all of us have that in a way that feels true and as real as our romantic relationships. And I was like, oh, right. So some people are starting over and building the friends they would actually choose after 50. And that is something that I really have to, I have really taken a step back when I get letters like this and say, okay, well, let's not assume that their best friend from college is someone they even like. LAURA STASSI Yeah. MEREDITH GOLDSTEIN Like, how do you go about building something new? Because I will tell you that in a romantic relationship, I feel that way, where I'm like, well, this is a brand-new experience for me. And some of the things that I should know really well, especially with my day job, feel like, weirdly unfamiliar. So I am calling upon my own column and letter writers to say, well, what did people say? And vice versa. So that's what I would say is that I am every day imagining what it would be like to build the things I already have. LAURA STASSI Okay, is there anything else I need to know? MEREDITH GOLDSTEIN You know, listen, if anybody wants some feel-good advice, come to [email protected]. It's all anonymous. And I love, love …the best letters are from people over 50 because there's so much to say. END CREDITS Speed Dating While Gray audio production and mix is by Steve Lack: Audio. For more on the show, including how to get in touch with me, go to datingwhilegray.com. I’m Laura Stassi. Thanks 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 [email protected].