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“How Much Do I Say?”

Why Oh Why’s Andrea Silenzi on the decision to make her dating podcast personal.

Andrea and Leon.
Andrea Silenzi and Leon Neyfakh.

Photo illustration by Slate. Images by Ilana Millner and James Brandt.

Last week I sat down in one of Slate’s recording studios to talk to my friend and colleague Andrea Silenzi about the relaunch of her podcast, Why Oh Why. The podcast, which began in 2013 and relaunched this fall, is about love and dating. The purpose of my conversation with Andrea was to tease apart her knot of conflicted feelings about using her own personal life as fodder for the show.

More specifically, I wanted to hear her weigh the pros and cons of sharing with her listeners that, not long after this new season of Why Oh Why started, she and her boyfriend of several years—the person she had wanted to have children with—had broken up. Andrea met Mike while recording episode 11 of the original Why Oh Why. It happened thanks to an economist she had spoken to about how to make her dating life more efficient; he had recommended she use Skype to talk to people she matched with on Tinder before investing the time into actually going on dates with them. Mike was the first person Andrea tried it with, and because she was so devoted to her show, she got it all on tape.

When Andrea told me she was stepping down from her job as the producer of Slate’s daily podcast The Gist to revive her old radio show about dating, I worried that her status as happily devoted live-in girlfriend might be an obstacle. How would she know what to cover? How would she summon any urgency when exploring questions and problems that had nothing to do with her life? When she told me she and Mike had broken up, I couldn’t help but feel a little excitement for her and her listeners. Not only would Andrea be able to use the story of her return to dating as a plot device, she would also be much more invested in her subject matter.

Andrea wasn’t so sure, which is what prompted us to have this conversation. The extraordinary episode of Why Oh Why in which she took the plunge and told her audience about the breakup came out last week.

The current incarnation of Why Oh Why is a production of the Panoply network, which is a kind of sibling organization to Slate—both are part of the Slate Group. My conversation with Andrea is below. It has been edited and condensed.

Leon Neyfakh: I was curious, when I heard that you were starting the show again and that you had this very steady boyfriend, about how you were going to handle it, because it seemed like you would be making a show about something that was behind you—a process that you had gone through successfully and come out on the other side of. 

Andrea Silenzi: Yeah, and it was really awkward at first. When I recorded the single guy focus group episode, it was me alone, basically, with 10 guys, and I remember a moment when they all kind of looked at me and were like, “What’s your deal? What’s going on with you?”

Neyfakh: And, just so we get the chronology right here, what was your deal at the time?

Silenzi: I was very happily in a relationship! And during the whole focus group, all I could think about was how excited I was to go home and tell Mike how it went and how excited I was to go back to domestic bliss and how grateful I was that I wasn’t on any of these dating apps anymore. But I also felt kind of out of touch. That I hadn’t even looked at Tinder for a really long time.

Neyfakh: Did you feel like you were interested in what the guys were talking about?

Silenzi: I remember thinking about booking a dermatology appointment and planning to put some beans in my slow cooker when I got home. My head just wasn’t in the game. Dating is a thing I think is interesting—it’s a really formative time in a woman’s life. But I thought I’d met the love of my life! I thought I was never going to have to be out there again. And then about a week into making the show, Mike and I finally had the sober talk we’d been putting off, and it became really clear that it was time for me to move out. It was time to figure this out again.

Neyfakh: Did you think when you were starting the new version of the show that you might be at a disadvantage because you were in a relationship?

Silenzi: Something I worried about a lot was whether single people could connect with me in the way I wanted them to. I don’t think a journalist always has to be on the same plane as the subject in order to connect. But in my social life, my bonds with my single lady friends had suffered while I was living on Boyfriend Island. It was hard—we weren’t going out to bars together; we didn’t feel the same anxiety that we used to feel together.

Neyfakh: So now that you’re single again the problem is solved, right? You’re just going to fill the show with your personal observations and details about your own dating experiences?

Silenzi: I think it’s a bad idea. I’m ambivalent. I’m deeply ambivalent. How will I ever go on a date if any guy who shows up knows he might show up on my podcast? Anything they say to me, anything that happens in the bedroom, it’ll all be fair game now. How do I create something real in my actual life if anything I’m doing might just be a stunt for the podcast? Do you remember a time in your life when you did stuff, and you were like, “This’ll make a great story!” I’m past that now. I hope.

Neyfakh: I don’t really see you making decisions just because you think it’ll make for good radio. I think it would just make you more attuned to experiences you were going to have anyway.

Silenzi: But then how do you think I can do it without my audience turning on me? I once had an iTunes review where someone called me a “gaslighting narcissist.”

Neyfakh: Whoa. Why?

Silenzi: I think because of how much of me was bleeding into the show?

Neyfakh: I feel like we’re past that as a culture. I don’t see that being thrown around that much any more. I remember when female writers, especially, were treated dismissively because they were writing about their emotions and not “real things.” But first off, I don’t see it as much anymore because I think it’s been pretty handily dismantled as an argument. Second, I think people’s threshold for what they consider narcissism is a lot higher than it used to be. Mostly, though, I think it’s just really hard to argue that the inclusion of personal experience—in the context of journalism or really any kind of effort to communicate with people—would make something worse rather than better. It’s so much easier to touch people with stories when you can talk in the first person about how they made you feel.

Silenzi: I agree that my favorite moments in art and culture and definitely podcasting are moments when I feel like someone is revealing something incredibly true from their lives. One of the best podcast episodes of all time, even according to Slate, was when Louis C.K. and Marc Maron talked about their friendship.

Neyfakh: You said something else earlier that I think is a separate issue: How will you deal with the fact that potential boyfriends or people you go on dates with will be nervous about ending up on the show? Are they going to ask you to sign nondisclosure agreements before you get a drink? I think that’s a real concern, but it’s also a pretty universal concern for anyone who makes art or writes about his or her life, right? I mean, I think that’s an argument that’s been sort of settled in our culture too. And I think people have decided that you have to let the artists use what they have to use, and you can’t stay mad at them for too long.

Silenzi: Yeah. And that was the thing that changed about my last relationship. At the beginning he was really game for me to use whatever I needed to about what was going in in our life. But then as that door started to close and he wanted his privacy again, it was hard to imagine talking about love and relationships without including what we might have been experiencing or going through. Having that off the table felt really limiting. So I’m wondering, now, if I give my listeners that consistent level of intimacy again, will I ever be able to pull it back?

Neyfakh: I feel like you’re treating this as a door that you won’t be able to close behind you, and I don’t think that’s true. 

Silenzi: Hmm. I think it’s really true.

Neyfakh: I think it’s not true.

Silenzi: One of my favorite podcasts is a show called Millennial hosted by Megan Tan. It started with her talking about her search for a job in radio, which obviously I loved hearing about. But then she started to pivot into talking about other millennials, and I was like, But Megan! Megan! Come back! What’s going on with you? How’s your boyfriend? How’s your boyfriend’s dad? How’s your mom? How’s your dad? I needed to know everything about Megan. And I had a really hard time paying attention if Megan wasn’t talking about Megan. So, I see that impulse inside of me, and I wonder if that will happen to my listeners if I ever pull back from talking about my life.

Neyfakh: But you’re already in the show! You may be playing the role of narrator, but it’s a very intimate mode of narration. You’re the main character no matter what you’re talking about. I feel like I’m checking in on you that week when I listen to it. Sometimes that’s gonna take the form of you interviewing someone else about their life, but it will always be informed by who you are.

Silenzi: But if my life goes the way I want it to, I want everything in my life to be really boring in the future. A year from now I’d like to have nothing going on that I could really report. You’re listening to Why Oh Why. My dog looked really cute on her walk today, and then my really nice new boyfriend complimented my dress. Today on the show, I’ll tell you all about that dress. It has pockets.

Neyfakh: I don’t think you should feel obligated to give your listeners an update on how things are going. You’ll feel compelled to include things as they happen because they’ll be interesting, or because they’ll contain some kernel of truth or emotion that you want to share with your listeners. And you won’t do it unless you have that. I don’t see the problem.

Silenzi: But because the show is about dating, won’t that compel me to stay perpetually single?

Neyfakh: So you’re wondering if you want to set the expectation up by opening that window and then risking the possibility that people will be alienated or disappointed when you find that boring boyfriend who likes your dress and you close the window.

Silenzi: So then I’ll be an old woman and people will say, “Were you ever married?” And I’ll say, “No, but I had a podcast.”

Neyfakh: So you’re worried about ruining the podcast and ruining your life. I’m starting to understand the stakes here.

Silenzi: I don’t think it’s an out-of-scale worry. I think these are really important questions I should ask before making a decision like this.

Neyfakh: So let me stop trying to convince you and ask you: Why are you ambivalent? If those are the things you stand to lose, what makes you want to do this? Because you clearly want to a little bit, right? Otherwise we wouldn’t be having this conversation.

Silenzi: Well, how great was the first season of StartUp?

Neyfakh: Really, really good!

Silenzi: Right. And that was because Alex [Blumberg] knew how to use himself as a tool for understanding this larger story about starting a business. And the quality of the tape in that season—the conversations with his wife, the conversations with his investors—came from his experience as an incredible radio producer. So I have this dream that I could do for Why Oh Why what StartUp season 1 did for Gimlet, where people will be so rooting for me and my quest to find a best friend to have sex with that they’ll all subscribe and tell their friends to subscribe. So I feel pressure to mimic what I see great podcasts doing—while also being very fearful that if I do, it makes the show less sustainable over time and it makes the show more of an invasion into my life.

Neyfakh: What other advantages do you see?

Silenzi: It’s just my favorite kind of thing to listen to.

Neyfakh: What is?

Silenzi: People talking honestly about themselves. That’s all I’ve ever loved about every podcast I’ve ever loved, is feeling like I know the host and I’ve connected to them without actually having to hang out with them.

Neyfakh: This might be because I actually know you but I feel that way about your show already, for what it’s worth. I don’t think you need to speak in the first person in the way we’re talking about in order to achieve that intimacy.

Silenzi: Aha. So maybe I could say, “Hey guys, I’m single now,” and then have that be enough. And then I can keep going with the same amount of self-revealing as I had before?

Neyfakh: Yeah. I don’t think it would be that jarring! I think the show’s already very intimate.

Silenzi: Do you think you’re less fearful about using your own life in your writing because you’re a dude?

Neyfakh: I’m definitely aware that writing memoir is a more loaded undertaking for women because for whatever reason a lot of women were criticized for doing it and were treated as unserious for “looking inward” instead of “out at the world.”

Silenzi: Yeah. But then I think the echo of that is that it’s hard to be a lady writer and not feel pressure at some stage in your career to write about your dating life.

Neyfakh: To cash in on your allure as a woman.

Silenzi: To go all Carrie Brownstein on it. Or, wait. Wrong Carrie.

Neyfakh: Wrong Carrie. Though Carrie Brownstein wrote a memoir. I don’t know how personal it is.

Silenzi: I hope it is personal!

Neyfakh: I forgot about Sex and the City. That should have been our touchstone from the beginning. I mean, that show literally is her narrating her dating life in a way that also connects to the dating lives of others. But I don’t think you should treat that as a model. I just think you should be open, when you’re out there having experiences, to the possibility that you’ll go through something special that you’ll want to communicate to your listeners. And when you want to, you’ll do it, and when you don’t, you won’t.

Silenzi: Yeah. I’m not going to record every date.

Neyfakh: Wait, is that what you’ve been imagining? Maybe we’ve been imagining two different things. If that’s what you’re imagining, I can understand your trepidation. But you don’t need to do that.

Silenzi: No, but my brain won’t switch off from work. If I were to be on a date, I would be constantly looking for observations I could feed into the show. And that can be a really addictive place to be, feeling like you’re on assignment.

Neyfakh: Yeah. That’s what I was trying to say earlier—that you would tap into that hypersensitivity. But maybe that’s bad—maybe that will result in dates that don’t feel real or something. I don’t know you well enough to predict whether that’ll happen to you. But I think you could handle it.

Silenzi: You’re right, there’s a huge spectrum between recording every date and keeping some details in mind and then bringing them up on the show later.

Neyfakh: Yeah. Definitely.

Silenzi: I think I’ll play it on a case-by-case basis.

Neyfakh: And so, you’re going to devote part of your next episode to talking about your breakup?

Silenzi: Yeah. How much do I say? Do I say why we broke up?

Neyfakh: You don’t have to. But people will probably want to know.