Meet your heroes
the thrill of connecting with actor and comedian Jeff Hiller, whose art I love
It was about two and a half years ago that I first really got to know Jeff Hiller’s work. He’s long performed in improv and acted on TV and Broadway, but the HBO show Somebody Somewhere was my first introduction to his comedy and his incredible range. (He has a knack for making me both shriek with laughter and burst into tears.)
If you don’t yet know the show Somebody Somewhere, read this piece about the show’s opening season by Sarah Baird that really captures the show’s pitch-perfect depiction of rural characters, particularly queer people in small towns.
Not long after I watched the first few episodes of Season One, I concocted a reason to reach out to him: a karaoke singalong party at WNYC in New York, where Death, Sex & Money was produced at the time.
And Jeff came to our karaoke singalong party! And he killed with his rendition of Alanis’ "You Oughta Know.”
This week on our new episode of Death, Sex & Money, you can get to know more about Jeff Hiller and his family, his body of work, and how he first tried improv after doing social work right out of college.
There are so many moments in our conversation that when I can call back up, I crack up all over again. Listen here.
The series finale of Somebody Somewhere airs on Sunday, December 8.
Speaking of Improv….
Come out on Friday, January 31, for a Death, Sex & Money live show I’m hosting as part of SF Sketchfest, the comedy and improv festival in San Francisco. Get tickets here.
Guests will include writer and artist Chanel Miller and comedian and SNL writer Carl Tart.
Again, get tickets here while you can!
Your stories and updates about estrangement
After we shared our episode about estrangement last week, many of you have reached out to deathsexmoney@slate.com to share emails and voice memos about your own stories of sustained distance from once-close relationships.
We are still listening through to your stories, but I wanted to share this story we got from a listener named Megan, who first heard our series back in 2022 and reached out to tell us what’s happened since:
I wanted to take a moment to thank you for re-releasing the "Why I Chose Estrangement" episode….I’m deeply grateful for your estrangement series. When I listened to the episode where Anna interviewed Rebecca Martinez Fitzgerald, the therapist from Durham who specializes in helping people navigate estrangement, it felt like the stars aligned.…After listening to the episode, I reached out to Rebecca. She connected me with her estrangement support group co-lead, who is now my amazing therapist.
Long story short: THANK YOU for helping me find the best therapist and for shedding light on this important, often overlooked topic.
I’ve been estranged from my mother for about 4.5 years. Through counseling, I’ve come to understand that my mom is a narcissist and a master manipulator. It’s been challenging to open up to friends about my family dynamics—not just because of how painful they’ve been, but also because of the deep sadness of not having a mother in my life due to her mental illness. My sister and brother still have relationships with her, and I know she wants me back in her life. But the pain she’s caused has been too much to bear.
What I’m struggling with now is figuring out when, or if, this estrangement ends. How long do I go without speaking to her?…It’s a constant ebb and flow of grief and pain, mixed with the reminder that I need to uphold my boundaries….Thank you again for creating this series and fostering these conversations. It helped me find connection in a new place and has greatly improved my ability to hold boundaries and space for these types of conversations!
-Megan
…And Speaking of Belting Out Our Favorite Songs…
I also want to make sure you don’t miss a very special SLATE PLUS treat this week. Writer Heather Havrilesky reads me an essay I haven’t been able to get out of my head for a year about the magic of singing lessons over Zoom, and she doesn’t just tell, SHE SHOWS. Spoiler: her voice singing “I Don’t Know How to Love Him” from Jesus Christ Superstar is really beautiful.
Long-time DSM listeners may remember Heather from this fun episode about romance advice in 2022, and if not, check it out: Affairs, Throuples, and Big Monogamy: Your Relationship Questions Answered.

Become a Slate Plus member to listen here. Slate Plus membership is a gift to yourself that will keep on giving, with ad-free listening to all Slate podcasts and extra drops from us.
Until next week,
Anna
Listen to our latest Death, Sex & Money episodes
12/4 From Social Work to Improv to the Best Show on HBO (Apple|Spotify|Slate)
12/4 Plus: Heather Havrilesky on The Transcendent Power of Low-Stakes Art (Apple|Spotify|Slate)
11/26 Why I Chose Estrangement (Apple|Spotify|Slate)
11/19 How a Betrayed Spouse Became an Infidelity Expert (Apple|Spotify|Slate)
11/19 Plus: Divorce is Illegal in My Country. Here’s How I Escaped My Marriage. (Apple|Spotify|Slate)
11/12 Will He Still Love Me When I’m Off Ozempic? (Apple|Spotify|Slate)
11/12 Plus: A Body Positive Educator Contends with Her Eating Disorder (Apple|Spotify|Slate)
11/5 A Celebration (and Critique) of American Freedom (Apple|Spotify|Slate)
10/29 The Making and Unmaking of a Productivity Perfectionist (Apple|Spotify|Slate)
10/22 Haley Joel Osment Is Not Your Typical Former Child Star (Apple|Spotify|Slate)
10/22 Plus: The New Era of Pop Womanhood (Apple|Spotify|Slate)
10/15 Search Engine: When Is It Time To Stop Drinking? (Apple|Spotify|Slate)
10/8 My Father Planned His Death. I Didn’t Stop Him. (Apple|Spotify|Slate)
10/8 Plus: Two Sex Columnists on Tapping Turn-ons (Apple|Spotify|Slate)
Anna, I love this show so much and so excited you got to meet and play with Jeff Hiller. He's AMAZING. I featured somebody somewhere earlier this year in my Stack. I wanted to say that I am so glad you are bringing back the estrangement shows, as they were so impactful and led to me rethinking the memoir I was pitching that I've now sold. So much good stuff. Here's my post that mentions the show.
I loved this episode!