“I wouldn’t be able to keep doing my job,” says Fresh Air host Terry Gross, sitting in her book-lined office at Philadelphia’s WHYY radio station, “if I wasn’t still so curious about people.” That curiosity — the kind that can sustain a lifetime spent conducting revealing, penetrating interviews with artists and newsmakers — is even on display in the brief moments before our interview begins: Gross, a small woman in glasses and a leather jacket, asks a passing co-worker about her weekend plans, a visiting former intern about her current gig, and me about my trip from New York to Philly, my editing process, my career, the neighborhood where I live, what I thought about Lady Bird. And when I turn my recorder on, the 66-year-old — the country’s unofficial poet laureate of the interview — leans forward to listen even more closely. “If you’re willing,” says the NPR mainstay, “you can get an interview to a pretty real emotional place.” Or at least, she adds with a smile, “a place that isn’t boring.”

You’ve been interviewing people for more than 40 years. What do you think that’s taught you about yourself?

That’s hard. I’m not exactly sure I can enumerate what I’ve learned. It’s like you’re slowly being changed every day by doing this job. I have learned, though, that everybody is insecure and everybody is troubled. Even incredibly talented people have deep insecurities. Maybe this is perverse, but I find that idea comforting. It helps me cope with my own stuff.

What’s your stuff?

What’s my stuff?

Yeah, your stuff.

Okay, my stuff. Various insecurities. Nothing major, but an overactive mind that’s often focusing on the negative. Like, What’s bothering me today? Let me work that for a while. What’s making me most insecure? I’ll focus on that. What’s hurting? I’ll focus on that. Sometimes I think of myself as always having an antenna up, and it’s not always tuned to the most productive thing.

I’m probably just revealing my own neuroses here, but it sure seems that when people are presented with two pieces of information — one negative and one positive — the negative one almost always gets a lot more attention.

That’s exactly my problem.

So if somebody said to you, “Fresh Air is my favorite thing to listen to,” and then said, “Well, yesterday’s show wasn’t the best.”

Stop right there. I would totally dismiss the “favorite thing to listen to” part. I’d think that was just their way of cushioning the blow that yesterday’s show was terrible. They’d just come up with a false opening to be nice about how bad yesterday’s show was.

The behaviors you have to be comfortable with as the host of Fresh Air are behaviors that would be considered antisocial in almost every other context. Do you have to be weird to be the kind of interviewer you are?

You don’t have to be weird. I think what you have to do is really believe, as I do, that the interview serves a function.

What’s the function?

I like to quote John Updike on this. In his memoir, Self-Consciousness, which I really love, he said he wanted to use his life as “a specimen life, representative in its odd uniqueness of all the oddly unique lives in this world.” That’s kind of how I see interviews. When you’re talking to an artist, you can get insight into the sensibility that created his or her art and into the life that shaped that sensibility. I love making those connections. I think we all feel very alone. I don’t mean that we don’t have friends or lovers but that deep at our core we all have loneliness.

And want connection.

Yeah, we want connection and sometimes when you’re talking to an interviewer who you trust, you can speak in a way that’s different than the way you talk to friends. You can reveal more. Not always, but sometimes.

Do your guests have to like you for you to get to that level of connection?

I figured out pretty early on that I’m not the kind of person who’s doing interviews to be friends with the guests. I’m not trying to prove that I’m smart or funny. I just want the guests to say things of value. I want them to be interesting and I want them to say things that our listeners will want to hear without being embarrassed or harmed. I’m not saying we’re here to cover up a guest’s bad deeds. If there are bad deeds, we’ll either address them or we won’t do the interview in the first place.

This is maybe a strange direction to go in, but I interviewed Louis C.K. last year — he’s someone you had on the show a couple times — and I can’t help but feel that I should’ve pushed him harder about what were then the rumors of his sexual misdeeds. In retrospect, were journalists letting him off the hook these last few years by not asking him directly about those rumors?

I hadn’t heard the rumors. I really had not. What’s especially confounding for me is that I love Louis C.K.’s work so much. To find out what he’d done was deeply upsetting. It left me speechless.

But do interviewers have a responsibility to ask direct questions about rumors and allegations when it comes to subjects like sexual misconduct?

I’ll typically pass on the interview in a situation like that. I can’t sit in judgment of a person — I don’t know what happened. But if I am aware of allegations, I can’t not ask about them. And in that circumstance, the guest is unlikely to tell me the truth and we’re all likely to be very uncomfortable and feel as if something is going unsaid. So rather than create that situation, I’d prefer to just not do the interview. Without naming names, I’ve been in situations once or twice where I’ve found out about ugly accusations once it was too late for me to ask about them and I felt awful.

Awful because you thought you should have addressed whatever those accusations were?

Well, I didn’t even know that there was something to address and chances are I wouldn’t have done the interview if I had. I hate to talk in generalizations about this kind of thing but typically if there’s any kind of buzz about sexual misdeeds or something like that, I’ll sit the interview out. I just don’t feel like I’ll know enough, and if the person’s already denied things and I ask again and they deny it again, then what have we accomplished?

Along those lines, did you have any qualms about interviewing Woody Allen?

That interview was before the allegations that he’d abused his daughter. But I did ask him about Soon-Yi. I didn’t want to just say, “So, you married your daughter?” I kind of asked around it. I knew that he doesn’t talk about it or at least he didn’t at the time, so I just did this question about if he thinks it’s fair to judge somebody’s work based on their life. Needless to say, he didn’t think it was.

Flipping around a question I asked earlier: What can you say you’ve learned about other people from doing Fresh Air? Have all those thousands of interviews led to any general insights about human beings?

What can I say? You think you have meaningful conversations with someone, then you find out they masturbated in front of women. I always walk away from an interview — no matter how well it went — knowing that there’s so much that I don’t know about that person. So when you ask, “Have you learned things about people?” Yeah, I’ve learned you may think you know somebody based on an interview and you don’t necessarily. We’re all mysterious. We all have things we’re ashamed of. We’re all different, which is why people are interesting. I don’t think everybody’s equally interesting.

Maybe this is hard to discuss concretely, but can you describe the different tracks you’re going down in your mind as you’re doing an interview?

I’ll try to. There are several layers, which I’m sure you have too. There’s the layer that’s just trying to listen, and listening is surprisingly hard. People think when you interview that you talk a lot. Actually, I listen a lot. I talk very little. Listening sounds like it should be easy, but it’s not, because while I’m listening, I’m also thinking ahead. I’m thinking, Is this an interesting answer? If I was editing this answer what would I be editing out and what would I be keeping in? Because if I’m going to ask a follow-up question, I need to know if the listeners have heard what I’m following up on. So I’m thinking all that, and I’m also thinking, Is this interesting enough to follow up? If so, what is the follow-up? Or is this something I should just say, “Time to move onto another subject.” I’m also thinking, What’s that word on the tip of my tongue? And then I’m thinking, Oh, my producer laughed. That’s good. Or, My producer looks bored, that’s not good. So all that is happening at the same time as my mouth is moving and sometimes I’ll start talking and realize, I’m not sure what the question I’m trying to ask is. But it’s my turn to talk and there can’t be dead air while I’m thinking about what I want to say. There’s a lot going on.

When did you realize you were good at interviewing?

It was never about a realization that I was good at it. It was more that I knew I liked it and felt comfortable doing it.

You felt comfortable immediately?

When I found interviewing it was like, Oh yeah, I can do this. I started doing interviews because I had initially wanted to be a writer and by the time I was in college, I gave up on that. Then there was this kind of creative void that I had no idea how to fill. I can’t act or dance or sing, you know? But then I got a chance to do radio, which I would never have thought of.

Why not?

Because I’d only heard one woman on the radio: Alison Steele, the Nightbird. But as somebody who’s shy, radio gave me an opportunity to engage with people in a forthright way without it being about me. Once I had a microphone, “Why would you talk to me?” became “Now I have a reason to talk to you and you have a reason to talk to me. So let’s talk.”

Comfort obviously has a lot to do with why you’re so good at your job, but what clues were there in your life that suggested that interviewing was your true calling? Did your friends think of you as a good listener?

I don’t know that anybody thought one way or another about me as a listener.

But it can’t be a total coincidence that you’re the person who ended up thriving as the host of an interview show.

I don’t know, maybe people who knew me could trust me to keep a confidence. And I do think people thought of me as somebody who played fair. The other thing that prepared me to be an interviewer was being an English major. When you’re reading fiction, you’re becoming the narrator of the story.

It’s an act of empathy.

Yeah, you’re imagining living that person’s life and that’s part of what you do when you interview somebody. Part of the preparation is thinking, What’s it like to be this person? And then when you’re talking to the person it’s like, Wow, that person lived through that? Let me make some calculations about what that could be like, and ask them questions based off of how I’d feel if that happened to me.

Did your parents think being a radio interviewer was a natural fit for you?

They were very surprised about my job. I graduated high school in ’68 and got my B.A. in ’72 — there were almost no women on radio then. So my parents had no reason to think that I would find a home there. I don’t think my parents had heard interviews on the radio. I think what changed their minds about my job — and made them realize it was an actual thing — was when I was still in Buffalo at WBFO. [NPR’s] All Things Considered was a new show back then, and it went on the road to develop stories that had a local angle — I did one of those stories when it came to Buffalo. Having a story that aired on a national show and that my parents could hear — that made them think, Oh, her work exists!

I’m still trying to understand what about your pre-radio life suggested that you’d be so emotionally and intellectually well-suited for interviewing.

I don’t know!

Of all the people in the world, and all the jobs in the world …

I don’t think I can get to an answer through my parents because I never directly talked with them about whether they thought my job was a good fit for me. Once they realized I hosted a show and earned a genuine salary, they were thrilled but in terms of answering your question — I committed, you know? I wanted it so badly that I just devoted myself to it.

Ah, okay. So what need did Fresh Air fill in your life? Why did you want it so badly?

When I was in high school I wanted to write. And when I got to college, I still wanted to write but I was discouraged really quickly because, well, I had two freshman English teachers, and one of them thought that something I wrote was really great. He said something like, “This is the kind of language that can shatter.” My heart swelled. I was so excited. But then my other teacher said, “Okay, for your assignment, just write something and bring it in.” And I thought, Write what? I don’t have stories that just come to me. So I went up to this teacher after class and I said, “I don’t know what to write about.” He looked at me kind of smirky and said, “Write a love story.” I thought, That’s about the last thing I’d write. He’s just saying that because he thinks women should write love stories. He’s not the type who’d be reading love stories probably. It was so dismissive. I was discouraged really easily, I guess. But, also, I just didn’t think I was good enough to be writer. I didn’t feel desperate enough to pursue writing, but I desperately wanted to pursue something that I could be passionate about and when I stumbled into public radio, I found that thing.

And you were determined to hold on to it.

You could criticize me, you could insult me, you could mock me — it was all right, just let me keep doing the job. Because I was an English major, I loved to read and dissect what was being said and why it was being said and think about the language being used. Interviewing fit so many of my needs.

What’s a criticism you’ve gotten that you found helpful?

Sometimes you don’t know what a word means to the community that uses the word, so you have to get sensitized to language, and I’m sure I’ve said things in tactless ways. But I try to let any pointless misinterpretations and accusations roll off my back.

I know there were listeners who thought you were overly moralizing or a scold, basically, when you interviewed Quentin Tarantino around the time of Django Unchained.

I really wanted to know his position on cinematic violence! When that movie came out, the Sandy Hook shooting had just happened, and Django Unchained was this incredibly violent movie — Quentin Tarantino’s stylized kind of violence. It’s kind of glorying in the violence. And I wanted to know if that violence read differently after all those children were killed by a gun. [Tarantino] interpreted that, I think, as meaning, “It’s your fault, Quentin Tarantino.” Which I didn’t mean at all. It disappointed me that he got testy about it and took it as moral judgment of his movie, as opposed to an opportunity to reflect on an issue that was staring us in the face.

My sense is that some listeners believe you’re tougher on guests whose politics they think you disagree with. And my assumption is that people who believe that kind of thing are just projecting an idea about what your politics might be because they don’t like your line of questioning. How much do you think people are just hearing what they want to hear in your questions and tone?

People are always projecting things. They’re hearing things that weren’t said or projecting meaning that was not intended and, perhaps, not even implied. I’ve gotten both insults and compliments for interviews I’ve never done. What can you do? There’s no way of controlling what people think. I do have a bullshit detector and it’s something I’ll use, but I do think I try and be empathetic to everyone I interview regardless of their politics.

Can empathy be learned?

I’m not so sure. I think you can learn to be a better listener and to focus better, but some people are just naturally not attuned to others. Even if they’re listening, they’re not picking up on the emotional meanings. I don’t know that you can teach emotional understanding.

What’s a question you regret having asked a guest?

There are plenty of questions that I wished I’d asked in a clearer way. You know about that whole thing when I asked Hillary Clinton about gay marriage?

She thought you were trying to pin her as a hypocrite?

Which I wasn’t. I was thinking that you have to be practical in politics and maybe she had personally been for marriage equality sooner than she felt she could say in a productive public way when she was in office. Then when she was secretary of State and didn’t have to worry about being voted in, she could be an advocate for LGBTQ rights. As you can tell, what I was asking was unclear. I also think her answers were guarded and unclear. But I wish I had asked that question better.

Is there a question you wish you’d asked in your life?

About my life?

To someone in your life.

I wish I could’ve asked my parents more about how they felt about dying. It’s the kind of question I ask guests, but my parents would wave me away if I tried to talk about that subject with them. I think they were trying to spare me, but also that maybe they didn’t have the language to talk about death. I don’t know. They were children of Eastern European immigrants who grew up without the language of psychology and philosophy. My father, I’m not sure he ever read a novel. There’s a certain kind of introspective language he might not have had access to.

He probably wasn’t encouraged to use it even if he did.

Absolutely. But it’s not like things ended badly between us and we needed to declare our love for each other and never did. That was all fine. We just never had the conversation. When my mother was in hospice and we were offered chaplains and social workers and stuff like that my father was like, “No, thank you.” He was uninterested, and I didn’t want to tell him what he should be feeling.

How do you feel about dying?

I’m not afraid of it. What I’m afraid of is pain. I’m really afraid of suffering. I’m afraid of being trapped in a hospital incapacitated.

But the prospect of not existing isn’t scary to you.

No, it’s not. I also don’t believe in a literal heaven and hell. I don’t think that there’s going be an accounting and I’m going to be sent to a place where I’m burning in flames.

What if it was all harps and angels?

Whatever it is, I’m not afraid of what happens after death.

Unless it hurts.

Then I’d be very afraid.

There was a New York Times Magazine profile of you a few years back, and in it you said that radio listeners create the identity of the person they’re listening to. Who is Terry Gross in the minds of Fresh Air listeners?

I’ve learned a lot about this from Twitter. Anytime I ask a question relating to sex, people go “Whoa!” They often quote back the phrase with the sexual reference as if it’s really remarkable. Like, “She said something sexually related!”

What’s that about?

I think it’s probably younger people thinking of me as the “older” person. Kind of like how you don’t want to hear your mother talk about sex. But the truth is I read these things on Twitter and I don’t get to ask the people tweeting them so I don’t really know why they’re saying what they say. Also what people find hilarious is when I have to talk around sex because of the standards of some of the stations that carry the show. So sometimes instead of saying “orgasm” or “oral sex” or “cunnilingus” or “clitoris,” I have to come up with all these weird constructions to communicate to people what I’m saying without actually it.

“Moment of release” instead of ejaculation — that kind of thing?

Yes, I’m trying to think of one. I don’t know, “self-pleasuring” instead of “masturbation.” I really tie myself in knots trying to say things like that. People find that hilarious, for good reason.

How does your work spill over into your personal life? And I mean more from a psychical rather than practical perspective. How does having deep conversations day after day affect you?

Okay, one of the things I’ve learned how to do on the air is make people stop talking. Some people can go on for seven minutes without a breath. At some point, you have to interrupt them and explain, “This is radio. We need to take breaks. We have to have, say, two-minute answers, or else we’re only going to be able to ask about three questions.”

I just asked about how your work spills into your personal life and you gave an answer that was only about your work.

Oh! I’m not going to make the case that I’m a great interviewee! I wasn’t intentionally avoiding the question. I was just going on a tangent.

Maybe you were unconsciously avoiding it.

No, no. I’m happy to address the subject. What I was saying actually connects to your connection. In real life, you’ll run into someone on the street and say, “Hi, how are you?” and seven minutes later they’re still telling you. So I’ve gotten practice with asking people in a nice way to stop talking. Some people act like they’re a late-night radio host alone in the studio and they’re rapping out loud to an audience that has no ability to talk back. I don’t want to be in that audience. I want people to talk with me, not to me.

Sometimes I find that in social situations I’ll often default to doing what I do at work, which is asking a lot of questions, and I think that’s at least in part because I find it easier to do that than to talk about myself. Are there any similar ways in which your job bleeds into your daily interactions?

Well, it’s made talking to people easier. I used to be really shy and now I feel like I can talk to anybody. I know I can ask questions that will help me find common ground. I can navigate to the place where me and another person can have a real conversation.

Do you find that the people who you talk to in your personal life expect a certain intensity to the conversation?

Sometimes I feel like people want the experience of being interviewed. But off the air, I like to be not the interviewer. I want to engage with the person I’m talking to on an equal level.

As interlocutors.

Have you ever been exactly sure what that means?

Definitely not.

[Laughs] What I like is to have a genuine back-and-forth: Here’s how you feel, here’s how I feel. Here’s my reaction to you, here’s your reaction to me. That’s as opposed to just “tell me more about you.” In an interview, I like to hang back. It’s not about me. If I made the interviews about me, we’d be talking about the book I read that day, because that’s how I spend all my time — preparing for the show.

How often are you recognized by your voice?

You know, a long time ago I was buying a car, which is a terrifying experience for me. Making big investments is excruciating, and deciding which car and what options and you know that you’re getting screwed by the guy selling it to you: It’s all the things I hate doing combined into one package. So I had to buy a car — this was the ’70s and or maybe the early ’80s — and I wanted to hear the car’s radio and make sure the speakers were good. So I was trying out a car and I tuned into WHYY, where Fresh Air was then a local show that I hosted, and the guy who’s selling me the car says, “Oh, I know that station. You know that lady in the afternoon? That really annoying lady?” And I said, “Oh, uh, that’s me.” And he smacked his head and went, “I’m never gonna be able to sell you the car now.”

You were in perfect bargaining position!

And I did end up buying the car from him. I didn’t care about his taste in radio, I just wanted a good deal, and he gave me the best numbers.

Does getting recognized like that happen a lot?

It happens more and more. The weird thing now is that someone will tweet and say they heard me talking at the grocery store or something like that. It gives me a sense of being watched when I think I’m invisible. I used to think of myself as nondescript. Outside of being short, I’m not the kind of person who is visually memorable. I don’t mean to disparage myself, but some people are striking because they’re so beautiful or they’re so tall and I’m short — it’s easy to not notice me. To be noticed when you don’t think of yourself as being noticeable is a little spooky.

You’ve said before, in various places, that all the prep time your job requires means you’re not the best at cultivating friendships. But I wonder if talking with people every day for Fresh Air satisfies some of the needs you might otherwise have for emotional connection.

That’s a really good question. My work days are so rich in terms of connecting with people. In addition to having what I hope are meaningful conversations on the air, I love the people I work with and we interact on a deep level. We go through a lot together and, yeah, I’m kind of emotionally exhausted when I’m done with the day. Then I’ll have dinner with my husband and we’ll have a pretty rich talk and after that I’m reading a book or watching something for work. There’s not a lot of time for other connection.

You and your husband listen to records together, right?

Every Saturday morning.

What’s the last one you were both into?

My husband goes to like the used-record stores a lot, and he found this French recording from the 1970s of somebody named Graeme Allwright singing Leonard Cohen songs in French. That was kind of a nice artifact. And we love hearing people do standards. You know how on the flip sides of 45s groups would cover an old song? Or on albums if they needed to fill time they’d do the same thing. Francis picked up an interesting Little Anthony and the Imperials album that featured covers of songs like “Over the Rainbow,” “Don’t Get Around Much Anymore,” “I’ll Never Smile Again.”

I apologize if this is an invasive question, but given that you’ve been doing this show as long as you have, and that you’re 66 years old, do you have any sense of the ending for you and Fresh Air?

Oh, I don’t. I’m not ready to stop and I’m not ready to have a stop date. I want to do whatever it is that I need to do to keep going. I’m not looking to retire.

Have you ever had offers to leave Fresh Air?

I’ve had offers, which I won’t discuss. I’ve been incredibly lucky to have the opportunity to keep growing this show, and continuing to do that is so exciting to me.

Who would be your ideal last guest?

No one! I’m not thinking of a final guest! I don’t have fantasy guests anymore.

“Anymore” — why not?

Once the show went national, and that was, like, 30 years ago, we had a dream list and we got most of those people. Lou Reed, Stephen Sondheim, Dennis Hopper. I think John Updike was on it. Lou Reed walked out on me.

Do you take bad interviews personally?

No. The thing I tell myself in situations like that is that these people don’t know who I am. Lou Reed, Bill O’Reilly, Gene Simmons — they don’t know who I really am. They have some stereotype of the public-radio person or the lady interviewer — because it’s usually people who don’t know the show that are the ones who walk out. The people who know the show, know what to expect.

Have you learned any reliable tricks over the years for how to salvage an interview that’s tanking?

Sometimes if somebody’s like a little too low-key, I find myself maybe talking faster to compensate, Like, Match me up here! Match me louder and faster!

Does that actually work?

[Laughs] No, I don’t think so. What I’m really trying to do is find the person’s comfort zone. Some people are great on craft — the process of writing, the process of making the film. Some people are great on anecdote. Some people are great on biography, their personal story. So I’ll just keep looking for that spot.

You’re fishing.

Yeah, I’m fishing. Sometimes I never catch anything. I can’t argue that every interview I do is interesting. Sometimes we don’t run interviews because they’re boring or confusing. You don’t want to hurt the interviewee’s feelings but your first responsibility is to offer something interesting to your audience.

Is there an interview that stands out for you as an example of your being able to take the conversation to an especially revealing place? What’s an interview that felt like a breakthrough for you?

Gosh, it’s hard to think of one. I’d say the Maurice Sendak interview. He was in this very reflective place and it was this beautiful and heartbreaking interview. It stopped people dead in their tracks. He was talking about his love of life and how he’d be crying his way to the grave, knowing that he’d be missing the trees and missing the music he loved. You could hear in his voice that he was tearing up. It’s probably the interview that surprised me more than any other I’ve ever done.

Though you’re saying it’s for reasons having less to do with you than him.

Well, I think he trusted me because I had interviewed him several times before. We always got along really well, and to hear him be so energized by the beauty of life at the very end of his own life was revelatory. I don’t know how he sounded the day after or the day before our interview, but in that moment he was appreciating the beauty of life. It felt profound.

Whatever the gig, it’s rare that someone has the same job for as long as you’ve had yours. Do you ever find yourself thinking any paths-not-taken thoughts?

I found the job that was best-suited for me. I would’ve wanted to be a singer, but it’s hard enough for me to hear my own voice, so that was never going to happen. I’m not sure — my job has had a bad effect on me physically. I’m either reading, screening something, listening to something, or talking to someone. It’s a sedentary life. I’m proof that you can hurt yourself by sitting and reading. I have back issues. Sitting’s also probably not good for your heart. I don’t have heart problems but when people talk about, like, aerobic exercise, I just stare at them blankly: “I’m sorry, what?”

What about non-physical downsides?

I don’t have children. I can’t say that was a sacrifice. I didn’t feel called to have children. I know I’ve missed out on something special but I couldn’t possibly have done my job and be a parent. The show is premised on me preparing at night for the next day’s interview. Doing that with children would’ve made me a terrible mother. When I was growing up it was unheard of to not have children and if you didn’t have children, it meant that there was something physically wrong with you. The women in my neighborhood were full-time mothers and that’s not the life I wanted. So I went completely in the opposite direction and I’m not sorry. I made a choice about what I wanted and I’m glad I did.

Do you still sing?

Only in the kind of spaces that shy non-singers sing in. We’re talking about the shower, empty elevators, closets. I’ve had cats run from my singing.

No you haven’t.

That is literally true. Our current cat seems to tolerate my singing. The previous one would run away.

What about that? Is that something you took personally?

I kind of did. But I learned to live with it.

This interview has been edited and condensed from two conversations.