The 7 Hardest Conversations I've Ever Had On This Show

The 7 Hardest Conversations I've Ever Had On This Show

As the host of Death, Sex & Money, my job is to ask my guests to talk about the things "we think about a lot and need to talk about more." And sometimes, talking about hard things that you don’t have much practice talking about...can be unsettling and uncomfortable. It can also feel like the deepest exhale you didn’t know you were waiting for. I've experienced this as both an interviewer and as a participant in the conversations on this show.  We've been talking a lot about hard conversations recently, as my new book, "Let's Talk About Hard Things" is about to be released into the world. So today we thought we'd look back at seven moments in our show’s seven year (!) history that I remember as the squirmiest, most stomach-ache inducing, unsettling, powerful, hard—and, ultimately, some of the most meaningful—conversations that have ever happened on Death, Sex & Money.  Hear more of the interviews we excerpted in today's episode:  My Awkward Money Talk With Sallie Krawcheck Why She Steals: Your Reactions The Sex Worker Next Door Chaz Ebert On Life Without Roger A Son and His Mom Laugh Through Darkness (featuring Bex Montz and Katie Ryan) A Son, A Mother And Two Gun Crimes (featuring Dwayne Betts and Gloria Hill) Dan Savage Says Cheating Happens. And That's OK.

Episoder(150)

I Love My Dad, But I Don't Love Guns

I Love My Dad, But I Don't Love Guns

Back in the spring, we asked you to tell us about the hardest conversations you've ever had, and the ones you haven't had yet. A listener we're calling Jack wrote in about a conversation he wanted to ...

3 Nov 202134min

Order Up, Tapped Out: Life After Restaurant Burnout

Order Up, Tapped Out: Life After Restaurant Burnout

In the last few months, millions of restaurant and hospitality workers have left their jobs. Right now, there are more job openings in this field than ever before. For many of these workers, the pande...

27 Okt 202137min

Succession's J. Smith-Cameron On Old Haunts and New Normals

Succession's J. Smith-Cameron On Old Haunts and New Normals

A few weeks ago, I was back in New York City for the first time since 2019. It was great—I saw coworkers in person, and I had lunch at one of my old spots, the Waverly Diner, with actor J. Smith-Camer...

20 Okt 202134min

Dead People Don't Have Any Secrets

Dead People Don't Have Any Secrets

Three years into Amanda* and Sam*'s marriage, the couple found out that they were unexpectedly pregnant...with twins. Amanda says she took on the lion's share of the work at home while also juggling a...

6 Okt 202127min

Your Infertility Stories Have Many Different Endings

Your Infertility Stories Have Many Different Endings

Sometimes the path to parenthood isn’t a straight line. What happens when you hit speed bumps on the road to having kids? Earlier this year, I asked you about what happened when you realized becoming ...

29 Sep 202140min

"You Should Be Carrying This. Not Me."

"You Should Be Carrying This. Not Me."

When a listener named Chloe was in college, she says she was sexually assaulted at a party by a former classmate. She filed a police report, but her classmate was never charged with a crime. He left t...

22 Sep 202134min

When A Banker Became A Nun

When A Banker Became A Nun

Sister Josephine Garrett grew up Baptist and worked her way up the corporate ladder—eventually becoming a vice president at Bank of America, where she managed a few hundred employees. But after conver...

8 Sep 202125min

Decision Fatigue Is Real. We Called For Backup.

Decision Fatigue Is Real. We Called For Backup.

We recently asked you to tell us about the decisions you're struggling to make right now. There have been so many choices to make and risks to weigh lately, and after almost 18 months into this pandem...

1 Sep 202159min

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