I've never vocalized that.

It's just that it's so effing uncomfortable to talk about.

Honestly, I prefer to avoid, we avoid the subject.

I think we're gonna have to skip that question.

This makes me very uncomfortable.

We don't talk about it. I'm actually surprised that she says something about it to you, Anna. Because like we don't know you at all.

This is Death, Sex & Money from WNYC. I'm Anna Sale. This show is about the things we think about a lot and need to talk about more, as we say. Of course talking about hard things that you don't have much practice talking about out loud. Can be unsettling and uncomfortable. It can also feel like the deepest exhale you didn't know you were waiting for.

I've been a part of conversations that run that gamut while hosting this show. Sometimes as an interviewer, it feels like I'm witnessing someone name something that they never have before, which can seem liberating and empowering. And other times, I know, I hit on places where someone isn't ready to share, which is totally fine by me. Or when the person I'm talking to doesn't like what our conversation is making them realize about themselves.

In this episode, we're going to look back at seven moments in our show's seven year history of what I remember as some of our hardest conversations. I've been thinking back about this, because on May 4th, a book that I've been working on for years is coming out., It's called, Let's Talk About Hard Things. In it, I tried to write about what I've learned about how to approach these kinds of tender conversations and more importantly, why I think it's important to have them. Why it's important to try to have them.

We're going to start this episode with a moment of tension. When I made someone mad. People often ask me of death, sex, and money, what is the hardest thing to talk about? What do people most not want to talk about? And I, you know, I don't really love that question because I would frame it differently. Like death, sex and money are all hard things and they're hard for very different reasons. And whether they're hard for you depends a lot on the history that you bring to each of them. But I will say, what are we the most clumsy about talking about consistently? Money.

So that is the first moment. It was about money. I was speaking to Sallie Krawcheck back in 2016. She's a former big bank executive who went on to start a digital financial advisory firm targeted to women called Ellevest. And I asked her about that.

ANNA SALE: The thing about money is it's all relative. Does it feel awkward sometimes for you to be reaching out to women when you yourself have had such a different experience with money than the vast majority of women in America?

SALLIE KRAWCHECK: Not at all. If you're in some way saying that, Oh, Sallie, you've been fortunate in your life. And you know, you've, you've made money in your life. So you should go sit down at home and shut up and not start a new business, quite the opposite, and to say, well, you know what? I've been lucky, 'cause I made some money. I'm not going to do anything about it as ridiculous, quite the opposite.

AS: So you heard me saying you should not talk to people, you should go home and enjoy your money and not reach out?

SK: [Laughs] I heard something I didn't like. There was something in there I didn't like that I reacted to, I'm not quite sure what it was now, but dang it, Anna, no.

AS: [Laughs] Well, I, I can understand how that's, how that might've sounded. Um, but I, I do wonder about like when - money is so hard to talk about, and when I asked you about what the lesson was after your divorce about money, was you've got to have it. And like there's so much shame that that can trigger.

SK: Yeah.

AS: Like, well, I didn't have money when I got divorced and here's this woman telling me I should just have money.

SK: I've gotta tell you this whole conversation, I'm starting to pit out. I'm beginning to pit out, just the - you know, what's been so fascinating for me. The, you know, that you have made the point that I have made money in my life, which I have. Isn't it interesting I had to come back and tell you that I also lost a lot of money in my life as if I, if I'm apologizing for it. It's funny. You've made me feel quite defensive.

AS: I I'm, I I'm sorry.

SK: That's okay.

AS: I think that's what I think we're hitting on what's difficult.

SK: Yeah. Yeah. Not that I feel unladylike. I just, I don't know. I do recognize. It's a weird topic for us. It's part of what I'm trying to change by normalizing it. Um, but I also recognize that some portion of it - look, you know, I, nobody works, has worked harder than I have. And you know, we didn't talk about it but when the kids were little, as soon as they were asleep I was back writing research reports. I mean, I, I, I worked and worked and worked, but some part of it is, is just complete good fortune. My parents, where we started, we're taking out loans to give their children this leg up in life. Other people didn't have that, you know, the kids down the street didn't necessarily have that. And those things built up such that the money I was able to earn was some portion because of hard work, but some very good portion because of luck. And I think that's the thing that makes us feel, um, weird.

AS: Uh huh. I know, I know.

SK: Yeah. It is interesting how awkward it is to talk about it. Even though I talk about it in the abstract every day.

Shew, that moment, ugh! I actually think about this exchange on the show the most, as it applies to my personal life in conversations in my personal life, because it's not uncommon for me to notice that something I have said is, is going down the wrong way or is being perceived as an attack. And then I have to figure out my way back to being able to hear one another. Um, it is not easy, uh, but I will say I've had a lot of practice at this during pandemic era domestic conversations.

The second moment I want to share with you is about when I let some of you down, our listeners. We had an episode back in 2017, where I had a very candid conversation with a woman who routinely shoplifted. Sometimes for things to feed her family, sometimes just for nice luxuries for herself like expensive makeup. And I asked her why she thought it was worth the risk.

AS: What would happen if you got caught?

ALICE (name changed): It depends on A) where you're caught, how much you're caught with, um, whether or not it's your first time. I - I'm a white female. So, I mean, I feel like I would get off a lot easier than some other people would?

AS: How does that feel to say out loud?

A: It's kind of disgusting to me, but I mean, it's how the world is. So I sort of use it to my advantage.

This episode struck a nerve with a lot of you. So much that we actually decided to make another episode, featuring your reactions, including from a listener named Trevor.

TREVOR: It was just hard to hear because as a black person, you're just like, okay, this is what we say is a problem. And here this white woman is admitting to, yeah, I probably get away with this because I'm white and you're just like - oh my god. It just, it just left such a bad taste in my mouth. It just was disgusting.

AS: You said in your comment, because of people like her, I'm the one followed around in the store.

T: Yes. Yeah. I mean, yeah. I mean, I've been this, I've never shoplifted in my adult life. I mean, I may have been a child because children don't know any better, they pick up things. Um, but I mean, as an adult, I've never stolen from the store, but I'm followed around the store constantly. And it's very frustrating cause you're just like, I make good money. Why would I be stealing from you?

A: And you also said this was a very problematic episode.

T: Oh my God. It was so problematic.

AS: Tell me about that.

T: Well, I mean, there was one instance and I'm not trying to call you out, but there was one -

AS: Please do! That's why I'm calling you, to call us out.

T: No, no, no. There was one instance where she hits at something and I was like, okay, Ms. Sale can go in there right now. And she can tell her as another white woman to another white woman. And it was just like, they missed that opportunity because she could have said something to her. Put her on the spotlight. Did you think that was right to be doing this? And I was just like, you didn't say it. And I was just like, you know what? It's okay. I'm not going to be mad at them, but because it was a difficult episode, it was just very difficult.

I hear Trevor there saying like, How could you hear the shoplifter say that she's a white woman, so she knows she's not going to get in trouble and you don't say, don't you think that's wrong? And don't you see, there are consequences for other people by you taking advantage of racism. And that's also like an interesting thing that I'm often thinking about during interviews. Like I know that listeners are sometimes thinking like, where's Anna calling out this person? And I'm always trying to balance that with really trying to continue to sort of dig in and pull out the person's internal monologue so I can understand. And I don't always get the mix right.

And now an encounter that came early in the show's history when I didn't really yet get, or, or fully appreciate just what asking questions could do. Like what an awesome, important responsibility it is to do that with care.

A woman we called Emma taught me that. Emma was a sex worker. We changed her voice in this episode you'll hear. And she first got in touch because she wanted to talk about her work. We did a long interview about the intimate massages she gave men for money, mostly men who were in other relationships. And after we talked, the next day, I got an email from her saying, please don't use our tape. And I said, okay, we can, we can keep talking about that. Um, let's take some time. And, and then I asked if I could talk to her again to understand what had happened after our first conversation. And a few months later, I called her back up and we talked again.

AS: Can you, can you wait, just go back to after the first time we talked and did a long interview, what happened afterwards for you?

EMMA: Well, I didn't sleep that night at all. And, um, I finally got up at, what was it like three or four in the morning, I got out of bed and I got on my computer and I started writing and I wrote you that letter. And, you know, had been working consistently for about six months almost, you know, almost every day. Seeing a client and, um - 

AS: Like seven days a week?

E: You know, five to six and, um, at least one person it's just every day, it's just something that I know is going to happen every day that I'm going to do every day. And, and so it was, it's a long time. I never gone that long without taking a break. And, um, So I think it was already kind of, it was wearing on me. And then just after talking to you, I just realized how much it was wearing on me, how much I needed to get away from it. And, um, and I just felt sick.

AS: How much time total did you take off this summer?

E: Probably two and a half months.

AS: Did you miss any of it?

E: No, not at all. No. Sure. The money, the income, the income I miss the, I miss the income, the safety net, the, the knowledge that as I'm putting money out, when I'm buying my food, that there's money coming in to replace that. I mean, I, is every time I get paid, I I'm immediately thinking this is going to pay for this, and this is going to pay for that. And when I'm not bringing in that income, I have that little sense of insecurity and a little bit of a fear. Like, am I going to be able to replace this? But no, I did. I didn't miss it.

AS: Have you had any of those feelings of dread since going back?

E: Yeah. Oh, you know, it's, it's hard to share these things because I can see somebody listening and, and like, why would you do this thing when you have dread? And even I think about other sex workers listening to this, and, and that's kind of one of my fears, another fear with this interview is to have sex workers listening to me and getting mad at me too, for representing the downside, the hard part. But yeah. Honestly, if I didn't have, if I didn't choose to do it, if I wasn't doing it, I'd be, I, I just have happy days. Every day that I know that I'm going to go see somebody I have some dread. And, and now I'm looking at another, probably four or five months, at least before I have a break, how am I going to do this every day?

AS: And Emma just want to kind of hear you in your own words or say like, why did you decide to talk to me?

E: I think, because I feel so alone. Um, one of the things that's really hard is not being able to talk to anybody and I'm, you know, I'm a mom I'm around other women and everybody talks about. There challenges or things that are hard in their life and things that are going well. And I just have this big secret that I can't tell anybody. And I think people need to know because there's a lot of people like me, I'm I'm right there. And you just don't know. So that's why.

That interview with Emma taught me a lot about aftercare and interviewing. That we really want to understand what happens to the person I've talked to after the interview is over. Because that can also be part of the story.

There've also been many moments during interviews I do for this show where I stop and check in with the person I'm talking with, because I can tell that the conversation has become hard or complicated for them, or just moved into a direction they didn't expect. One moment that comes to mind is when I was talking with Chaz Ebert, the widow of film critic Roger Ebert, who died in 2013, after more than a decade of living with cancer. A cancer that eventually took away his ability to speak.

CHAZ EBERT: Roger and I developed almost a mental telepathy. We were so in tune with each other that we actually could speak to each other without words, or without even being in the same room.

AS: Like a deep ability to understand what he was prompting? Like he what he wanted to communicate?

CE: I don't know - to me, I actually heard his voice in my head.

AS: Really.

CE: Yeah. And I know that happened sometimes, um, when he was in the hospital, I would wake up in the middle of the night and I would call the hospital and I would say. Oh, my God. He is so cold. Will you please go in and put a warming blanket on him? And the nurse would come back and say, how do you know, did he call you? And they would say, well, he couldn't call you. He can't speak. And I said, I don't know, but he just told me he was cold.

AS: Hmm.

CE: See, I, you know, I have to tell you, I knew you weren't going to ask me just the standard questions. I just knew it. And I had a little trepidation because I know I'm probably going to say things here that I probably shouldn't say, but -

AS: Well, I let's, let's actually pause and talk about that a bit. 'Cause I, in thinking about our conversation, I was wondering where those boundaries are for you, because - 

CE: No, the, you know what, I'm going to tell you, Anna, there are, there are none and that's why I was, uh, a little - no, you can just ask me anything and if something gets too hard or too, uh, I'll tell you.

AS: Okay.

CE: All right.

AS: Yeah. When was the last time you heard his voice in your, in your head?

CE: Very recently, he still talks to me. He does. He feels presence. And you hear it. I mean, you hear it. Yeah, I do.

That is Chaz Ebert talking with me a year after Roger's death, back in 2014.

Coming up, more moments of hard conversations from Death, Sex & Money.

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As we were making this episode, we were also reading and listening to your stories about hard conversations that you’ve been sending in. So many incredible emails have been pouring into our inbox. You’ve told us about confronting family secrets, navigating break ups, and finding the courage to deliver bad news, or just to address the elephant in the room.

Like this listener, Ashley. While she was in college, she was considering moving in with a new friend, a co-worker. But Ashley realized that she wanted to live alone. And after telling her friend that she’d changed her mind and found her own place, it wasn’t clear if their friendship would survive this:

ASHLEY: It wasn't until after the summer, when we were all moved in and we were all situated that I feel like we were able to start to move past it. I stopped thinking about it so much and, and really, I think it turned out all for the best because now that I know this person even better, I know that I think if we lived together, we would have hated each other. And now she's my closest, closest friends. And one of those friendships that's lasted for many, many years after such a time. Really uncomfortable conversation with her. And I know it seems silly because it's just a place to live, but it really was a big deal to the both of us at that time.

We’ll be sharing more of your hardest conversations in an upcoming episode. If you’d like to share one of your own, or to tell us about a conversation you’ve been meaning to have, send us an email or a voice message at death sex money at wnyc dot org.

And on the next episode, I’ll be answering some hard questions too. NPR’s Noel King will be interviewing me about my new book, Let’s Talk About Hard Things…we’ll talk about some of the things about my own life that I wrote about for the first time. And I’ll tell you, writing about them is one thing… talking about them is a whole other thing. Don't miss it. 

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This is Death, Sex & Money from WNYC. I'm Anna Sale.

When we started this show back in 2014, I was in a really different life phase. I was single, but in a relationship having just been through a big bout of angst, having to do with long distance. Then a year after the show started, I got married and then I had a baby, and then I had another baby. And being a parent, I have to say, I think has changed the way I interview, because now I think about things from the perspective of the person I'm interviewing - and I also sort of automatically start to wonder about their parents' perspective. Like every moment of pain, the question pops up, what would I say if this were my kid? How would that feel?

That came up in a wonderful episode that we recorded with Bex Montz and his mother, Katie Ryan. I first met Bex when he got in touch when we asked for stories about near death experiences and Bex wrote in about surviving a suicide attempt. Bex told us that it happened just after he'd had top surgery and was living out as a trans man for the first time. And afterward I found myself wondering about his family. About what it was like to be as parent. And so I talked with Bex along with his mother, who's a doctor, an OB GYN. I asked her how the experience changed her.

KATIE RYAN: I've learned that I can't keep him safe. He doesn't share enough. He doesn't ask for help from me. So I, I, I know intellectually that providing, you know, room and board and, you know, access to a car that those things are helpful for him, but I can't keep him safe. I can't do that. He has to do that.

Do you -

I haven't been able to do it. I failed. Yeah.

So you've learned that, you've had to learn that.

I had to learn. I thought that, you know, sleeping on a mattress, outside his bedroom door and taking the door off the door jam would keep him safe. And it meant that, you know, he wasn't - yeah, it meant nothing. It meant that I was pissing him off 'cause he didn't have a door to his bedroom and I was sleeping on the floor, outside his bedroom because I couldn't trust him. And it didn't work.

Your face, Bex is such a big cringe, right now.

BEX MONTZ: Yeah. Yeah. I mean, cause it's, I mean, it's true. Like I can just, uh, I haven't made things easy on anybody and like that's obviously not a choice. Like I don't like purposely wake up in the morning and be like, today I'm going to be an asshole, but it also doesn't feel good. You know.

AS: Do you think about being a parent, Bex?

BM: Uh, not a lot. No. Um, I don't think that I could make the sacrifices required to be a good parent. I think that it's really hard to be a good parent. I think that like, mom has done a great job with it, but I don't think. I would be able to do it. Like, there's this thing that you love desperately and you always want to be around and progressively over the course of its life, as it gets more interesting, you have to let it go. And like, that's sounds awful. Like that sounds horrible. Like both of you guys are fucking idiots. Like that sounds awful. [Laughs] And like, yeah, I just, I think I'm too self centered.

KR: Do you think being a parent would take you out of yourself? That it would force you to stop spending so much time perseverating about things that don't need to be perseverated about, um, and fill your day with other stuff?

BM: I think that's idealistic. I don't think so. No. 'Cause, cause it's not like I, yeah, I think that it's idealistic. I think like, realistically it would be that way for awhile and I would try really hard, but in reality, like I'm going to deal with depression and anxiety and my issues around gender for the rest of my life. That sucks. And until I figure out how to deal with that in a constructive way, there is no way I'm going to bring another human being who has no say in it, there's no way I'm going to bring someone else into it. If someone wants to come in on this, like fine, that's, that's my dating profile. If someone wants to come in on this, [laughs] but like, I'm not going to force anyone, you know? 

AS: I have to say, when you said like, you guys are fucking crazy, like, I, I think. I have a five month old baby. Um, and hearing you, I have related to you Katie, more than I expected to in this conversation and the, um, this, the, the, the, the puzzle of having so much love to give to this, to your child, but needing to find just the right slots while the, where the let you give it.

KR: Yeah.

AS: And sometimes you try and then you ended up repelling them like the wrong side of a magnet, is such a daunting thing.

KR: I mean, I taught - parenting is it's crazy, you know, and obviously I take care of patients while they're pregnant and they think that this is the most complicated time of their life and it you're like, I can't even - I just let them think that this is the most complicated time of their life, because the reality is just literally unbelievable of the, um, responsibilities of being a parent. And it's just a huge job. Huge. And you can mess it up.

One other moment between a son and his mother that will always stay with me happened when I was interviewing Dwayne Betts. He's a poet and a writer who also served almost 10 years for armed robbery that he committed when he was 16. This interview, it was an extension of a series my WNYC colleagues were working on at the time about the juvenile justice system called Caught. The whole series is wonderful. Dwayne was a cohost. And I wanted to talk to Dwayne as an adult, along with his mother Gloria Hill, to hear about their experience with the system.

GLORIA HILL: So I think it was probably about 10 30, 11 o'clock at night that I received a phone call from Dwayne and he says, I'm locked up. Don't worry about it. I'll take care of it.

DWAYNE BETTS: [Laughs]

And I think I cursed him out.

No you didn't.

I'm pretty sure I did.

Were you angry at Dwayne?

I was angry with him in the beginning. I was, I wanted to choke him. I really did, because I didn't understand why or how he could get involved and do something like that. Because I've never had a gun, he's never - well, til then. And then it just seemed like everything that happened in my life involved the gun. Because I think right after I was called to active duty and I was a police. Well security. So everything just, it's just a weird time for me.

So you, your son goes to prison for a gun crime, and then you have to have a gun as part of your job.

Yeah. I mean, actually after that, just before his sentencing, I was raped by gunpoint. And then I was called to active duty to carry a gun.

You said you were, you were robbed at gunpoint?

Raped, raped at gunpoint.

I actually didn't think you were gonna say that on the, on the air, this has just taken a really tragic and devastating turn.

ASL Yeah. I didn't know that Gloria.

It's just like guns became a part of life.

And this is something you've you've known before, Dwayne?

Yeah. I found out when I came home. 

GH: It happened just before he was sentenced. So when I was going to court for Dwayne, I was also going for a court trial for myself. So I didn't tell him until he came home.

DB: Yeah. So I didn't, I didn't know. Um. Yeah, I didn't know.

AS: Was that person a stranger or someone you knew Gloria?

GH: Um, it was a stranger. I was actually on my way to work and I was at the bus stop and it was someone who came up from behind.

AS: And did he go to prison?

GH: You know, it took him, I think they did catch him. 'Cause I was like his third victim.

AS: Having been the victim of a gun crime, did it change at all the way that you, you saw your son's involvement in the system?

GH: It changed somewhat. I mean, I know Dwayne should be punished for what he did. That I was sure of, but as, as far as the amount of time that the judge gave Dwayne, I, I thought that was a bit extreme. But I do understand the crime and punishment.

That conversation with Dwayne and Gloria went on to explore for Dwayne, like how this has affected his deepest values and beliefs and how sometimes they crash against each other.

DB: I think that I have for a while struggled with what it meant for me. I mean, I committed a crime and in some ways I think that, um, this guy committed a crime and it was, it was horrible. But I think what I feel is that, um, I'm in the same category that he exists in. And, um, and that's a challenge. That's a challenge for me.

In a very different context, the last hard conversation, the seventh, that I want to share with you is an exchange I had with Dan Savage, the sex columnist, writer and podcast host. I was interviewing him about family and money and love. With a real curiosity about how he built this framework for sex, with integrity and consent. That is the foundation of the sex advice he's been giving for years. Because that framework does not include blindly accepting conventions, including conventions of monogamy. And we talked about that.

DAN SAVAGE: Everyone talks about non-monogamy or non-monogamous experiences in the context of a long-term committed couple as if those, you know, those two crazy people are tossing a box of nitroglycerin back and forth, and that just hasn't been the case for us.

AS: And what do you want to know about me?

DS: [Laughs] Are you in a committed relationship?

I am.

DS: Are you not monogamous?

AS: No, we're monogamous. yes. 

DS: So what would you do if you found out that he cheated, and what do you think he would do if he found out that you cheated? And cheating is something that will probably happen. Just put that out there first, the research, the data shows that roughly 50% of men, 50% of women in long-term relationships at some point will cheat. And those 50% of men are not married to those 50% of women. So it will touch almost all committed, monogamous relationships. So what's going to be your reaction if, and when that happens to you?

AS: I know, I mean, I read, I read you Dan Savage and you make me uncomfortable because I intellectually, I understand all this. I get desire. I get that it's not rational. And I get that it's, it's a real thing, but it, I don't know what I would do with the hurt. I would have - I have a really difficult time seeing a way outside of it being okay. Or seeing a way for it to be okay.

DS: Yeah. My advice would be if, and when it happens, you know what people always say, you know, when they talk about the people they love most in their lives, I would, you know, I would take a bullet for this person. I would, you know, walk through fire for this person. That's hurt. You're saying I would hurt for this person in a really profound and life-threatening way. I would take a bullet. I would walk through fire. Infidelity, when people believe in monogamy and monogamy is what they want, infidelity is that bullet. And so if you look at your husband and think I could take it bullet for that man - 

AS: We're not married yet. I'm not even there.

DS: If you looked at your partner and think this is someone, you know, I love you so much. I could take a bullet for you. Just if, and when it happens, remember that feeling because that's the moment where you take the bullet. And some people accuse me cause I'm pro you know, non-monogamy that I'm, you know, giving get out of jail free cards to serial adulterers or, and I'm not. People should honor the commitments that they make. If you make a monogamous commitment, you should attempt to keep it, attempt to honor it, do your best. And then if you, you know, if it happens to you, if you get cheated on. You know, what is love and what is forgiveness if you can't forgive the person you claim to love most in the world for a betrayal that really cuts you to the core? And I think these things should be - because infidelity is so common, these things should be thought about well in advance of them happening. 'Cause I think if you just set your mind to, that is something, as painful it is, that we can get through, love each other through, forgive each other for, you're likelier to actually get through it, love each other through it and forgive each other for it when it happens, if it happens.

Ugh. Listening back to that still gives me a stomach ache. The way he says, "If and when it happens." Which I know, that tells me what I hold most precious. Thank you, Dan Savage.

And thank you to all our listeners and our guests over these seven years who have been part of these hard conversations. There's a link in our show notes to all the episodes we have featured here. You can find our entire archives at deathsexmoney.org. And let me say one of the great things about having a podcast about hard things? You never run out of content. There are so many. So I look forward to many more hard conversations with you all.

I'm Anna Sale, and this is Death, Sex and Money from WNYC.