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Repost: Change Is A Work In Progress

In this episode, we check in with some of our most memorable letter writers from previous episodes. The Sugars find out if “Struggling” was kicked out of his mother’s house,...

35:15Mar 7, 2026

Repost: Should I Stay Or Go?

In this favorite episode from the archives, The Sugars give rapid fire answers to a handful of letters that are all centered around a theme. The theme for this episode...

34:09Feb 21, 2026

Rewind: A Spy In The House Of Love

Snooping on your spouse is generally ill-advised, but what if he or she has an addiction and is constantly lying about it? The Sugars and writer Ariel Levy answer this...

Jan 3, 2026

Rewind: There's just one thing

The Sugars read letters from four women who each have one not-so-tiny reservation about the men they’re dating. A Black woman is dating a white man who is unwilling to...

Dec 20, 2025

The universe has good news for the lost, lonely and heartsick. Dear Sugars — the cult-favorite advice column from The Rumpus — is back, but this time speaking right into your ears. Hosted by Cheryl Strayed and Steve Almond, the podcast fields all your questions — no matter how deep or dark — and offers radical empathy in return.

Rewind: Make the Call

In this encore "rapid fire" episode, the Sugars give brief answers to a handful of letters. This time, they challenge each other to make the call -- one way or...

39:31Oct 25, 2025

Rewind: Buyer's Remorse

Buzz Bissinger owns more than 100 pairs of leather pants and over 200 pairs of leather gloves, having spent more than $600,000 on leather goods in the span of three...

24:00Oct 11, 2025

Rewind: Talking About Privilege

Privilege comes in many forms: socio-economic privilege, gender privilege, heterosexual privilege, to name a few. In this episode, the Sugars reply to two letter writers who are facing different forms...

50:21Aug 2, 2025

Rewind: Career Vs. Love

You love your partner, you love your career... but they're pulling you in different directions. What do you do? In this favorite episode from the archives, The Sugars have help...

33:42Jun 21, 2025

Rewind: The Great Reckoning

Dear Sugars returns to Portland, Oregon, for another epic live show. Special guests Mitchell S. Jackson and Rebecca Skloot share the stage with the Sugars to tell stories of personal...

51:32May 24, 2025
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