On creating space for honest conversation

What is your go-to first question in an interview?

I think that an interview really starts the second people walk into the studio. You haven’t asked them their name or even said hello on mic, but they’re walking into the space and immediately you need to create an energy that feels at once professional, but also incredibly open, a space where they feel like they can be honest and want to be honest. For me, that usually means a light banter at the top. I’m trying to project this is a place where you can have your needs met. I would say my first question is “Do you need to use the bathroom?” And the work that that does, I think, is just make people feel like, “Okay, I am comfortable.”

Well, let me just say, if you need to use the bathroom, you are more than welcome to at any point.

Thank you. They don’t always take me up on it, but I think that sometimes people get intimidated walking into a studio, and just having a moment alone in the bathroom or getting water gives them a second to collect themselves.

But really when you’re getting into the conversation, I would say the first question I ask is normally trying to get them in the mindset of describing a scene or describing a space. So I’ll ask them, “What did X look like?” What I’m looking for when I ask people questions normally is something one of my producers calls “the look away,” which is when someone is going back into their memory and really living in that space, and often they’ll break eye contact with you and look away because they’re not really with you anymore. And that’s the goal, to get someone there as quickly as possible.

How is it different interviewing someone who isn’t interviewed often versus somebody who does lots of interviews?

Great question. Everyone I’ve talked to, this is either their first interview experience or one of their first. And very often, we’re talking about things out loud they don’t talk about with anyone except their closest friends or closest family. They’ve also opted into being interviewed by a podcast for the New York Times, so they want to be open. But what it means is that there’s a lot of trust that I need to gain pretty quickly, pretty early on. The types of interviews I’m doing are not “got you” interviews. It’s not like I’m going to ask them a question that’s supposed to trip them up. These really are questions about their own experience.

So one of the things I say at the top is like, “We can take a break. We can take a pause,” just like the bathroom thing. Take a sip of water. If you want to say something again, you absolutely can, but you’re the expert here. I’m just mining for details, mining for plot, mining for clarity, but you know all the answers. So I think just making people feel like they are experts because they are, because it’s their own life, is important.

I’ve done interviews where I’m getting one word answers or I’m getting vague platitudes and I’m like, “Oh man, okay, I have to dig a little bit more.” What do you do in that situation?

I’m constantly working on this skill and I have a whole team that helps me out. But I think if someone clams up, you can do a hard reset. So you can say, “Let’s actually both drink some water.” Or sometimes, you can ask them a question that you know you’re going to cut, like a question about the weather or what they ate for breakfast. Often when people clam up, it’s either a sign that they really don’t want to go there, in which case, you have to respect that in certain instances, or they just think that you’re expecting something from them in their answer that they’re not delivering.

Very often, I would say that the clamming up is just because people start almost listening to themselves talk, and I feel like the best interviews are when people aren’t functioning as a listener as well. They’re just open and a conduit of their own experience. This is a little bit tricky, but you can say, “It seems like you’re hesitant to go there. I wonder why.” But I think that the real trick is just maintaining a very open and curious and kind orientation towards the conversation because asking the same question over and over in vaguely different iterations isn’t going to get you somewhere, and that’s where being a creative interviewer comes in.

How do you prepare for an interview?

Well, the podcast itself is based off of Modern Love essays. So I read the essay, I talk with my team about what feels like the most interesting other avenue to explore. Very often, it’s what’s happened after the essay or a scene that was only touched on in the essay that we want to go deeper into, and then I plan out questions. The thing about interviewing is that ideally it should sound like a conversation. I feel like when I first started out, I was really wedded to the page and reading my questions word for word, and I wasn’t letting the conversation breathe and move in the directions it wanted to. So more and more, I use planning the structure of an interview as a guide, but especially when you’re in person, I want to be making eye contact and following the interview naturally.

I know what I want a peak of the interview to be, and I know where I want it to land, but very often, one or all of those things changes in the moment and I just have to stay flexible, which is hard sometimes because I’m nervous, too. I don’t say that [to them] because you don’t want two nervous people in a room, but it is nerve wracking to try to grow that trust with a total stranger because I don’t want to let them down either if they’re opening themselves up. I want to rise to meet them.

And you have to grow it in such a quick timeframe.

Yeah, and you don’t want to be too charming or too jokey. And you also don’t want to be too serious. It’s just a very fine line. I feel pretty socially intuitive. I feel one of my skills is reading a room or understanding when to make a joke, but there are a series of very quick calibrations you do. The second someone walks in, “Whoa, they look nervous. I should ask them if they want water. Whoa, I think that they’re coming in really hot. They’re talking really fast, and that’s also a sign of nerves, so maybe I’ll slow them down.” And sometimes, I’m wrong. I’ll make a joke and the person won’t respond and you have to do some recovery. But that kind of stuff is interesting to me.

How do you define success or failure in your work?

I think I’m figuring that out, but I think that it’s like you said, if someone’s giving you generalities or pat responses or, “It was great,” or, “She’s beautiful,” or, “That was really hard,” that feels unsuccessful to me, not because that’s not true, but because that doesn’t feel… I think it’s vulnerable to talk to anyone about something that’s happening in your life, but what we’re really looking for is a level of vulnerability that only comes when you have trust with the person that you’re talking to. It’s the difference between the barista asking you how you are and your best friend or your partner asking you how you are, you know what I mean? You’re going to unload on the person you’re close to and you’re going to brush off the person you’re not. And the thing is I’m closer to the barista to these people than I am to their partner or their best friend.

So what I’m looking for is as close to that experience of openness and unselfconscious vulnerability as possible. And you’re never going to completely get that, because again, people have a mic in front of them and they’re in the New York Times building. But the mark of success for me is those little flashes, those look aways, these little moments where I can sense that they are opening up in a, I think, beautiful and quite radical way because it’s very rare.

Has this role taught you anything new about love as a subject?

I don’t want to give a pat answer, but I do think actually the pat thing is true. To love is extremely brave, and people have said it, and there are songs written about it and books written about it, but it is. It’s extremely brave to feel and to feel deeply, and I think it’s extremely brave to talk to a stranger, aka me, about loving.

If I remember correctly, in college you were pretty involved in storytelling and radio, and you’ve hosted live events. I’m curious about how you see your career trajectory evolving, and if there’s anything you wish you had known or misconceptions you had about this field?

Yeah. I did a lot of storytelling in college. It was extremely informal. I found that I really enjoyed the process of helping people tell their stories. And so that led me right after college to work at The Moth, which is a nonprofit personal storytelling organization. I’ve worked at various journalistic places as well, and I’ve worked at places where we’ve made deeply reported stories with multiple sources. But my heart is in memoir. It’s in personal story because I think those are, at least for me, the most powerfully felt.

There’s just—I’m going to say brave again—but something that I felt was brave in college, getting up in front of a room of expectant peers to tell an embarrassing story. For sure I saw that at The Moth, people baring their souls to these crowded theaters. And now in these interviews, I talk to people about experiences that only they know about. Conversations are more invigorating to me when we’re both using “I.”

What do I wish I’d known? I think that there is a tendency to become a little bit jaded when you’re working with personal stories. You hear a lot of stories about grandparents and a lot of stories about meet-cutes and a lot of stories about moms. And I think the trick—and I think I’ve been successfully able to do this—is just to stay invigorated for these stories. We only have so many relations, or there’s only so many iterations of breakups, but each story is unique and exciting if you let it be. And really, what I mean by that is the thing that’s unique and exciting is the person. I think at a certain point a few years ago, I was like, “The bar’s incredibly high for a grandma story. I’ve heard so many of them.” I don’t think that’s the right orientation to the work. The right orientation is like, “Wow. Another grandma story. Let me figure out what’s different and exciting about this,” because I have my own grandma story, and I think it’s stunning, and you just need to figure out a way to tell it.

Do you have any desire to tell your own stories?

I wonder if doing this job has made me a little bit more nervous to tell my own story, just because I feel like I’m thinking a lot about what makes a good story, or I feel like the bar for my own self would be super high. Whereas in college, I was like, “Let me make a lot of people laugh. I want a cute boy to notice me on stage.” But right now, I’m less interested in cultivating my own skill in terms of storytelling, and I’m way more interested in figuring out different and more adept and more fluid and more compassionate ways to understand a story through conversation. I think that takes years of experience, but I’m very excited to do that. And maybe at some point I’ll think it’s important for me to get on the mic and tell my own story, but right now I’m not as interested in that.

Who do you think does this work really well?

I’m not trying to be twee about it, but I really think of great conversationalists in my life—my father is a person who you’ll send in to get a coffee at the coffee shop, and it’ll take 35 minutes, and you’re unclear why, and he comes back and he’s like, “We’re invited over to dinner.” He just has this orientation in the world where people want to open up to him.

Having a conversation at a restaurant or whatever is incredibly different than having a conversation in a studio at night; I don’t have any illusions about that, but I really think that the people I admire are the people where you go to dinner with a friend and you find yourself talking for 25 minutes about a thing you haven’t told anyone about, those moments—this is a little bit intimate—where you’re lying in bed with a partner and the lights are off and you’re both looking at the ceiling and speaking in a pretty unfiltered way. These moments of openness are extremely inspiring to me. And at least for this show, what I’m trying to do is be an open, curious, engaged listener. So yeah, I think of my dad and I think about dinners with friends. I think about road trips when you have seven hours and you got to fill the space somehow because music sucks and you don’t want to listen to a single podcast. Those are the moments that I’m inspired by.