10 of life's biggest questions, answered with radical compassion: Recent Episodes

Dear Sugar

This is Amory Sivertson, the producer of Dear Sugar Radio. Here’s a “Greatest Hits” playlist for people who are new to Dear Sugar. The list was assembled in part via a social media call-out to our fans, and by looking at which episodes have generated the most listener response in our email inbox. But I was also looking to show the range of topics the show covers – from friendship, to polyamory, to family relations, to losing a loved one, to following your dreams. Steve and Cheryl don’t shy away from anything.

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This is perhaps the most personal episode of Dear Sugar for Steve and Cheryl. It focuses on how to be there for your parents at the end of their lives while staying true to yourself.

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This episode is a good reminder that not all women are aching for a partner, and that’s just dandy.

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This live episode proves that the Sugars are exactly what they sound like – very good friends, jokesters, unscripted, honest and always radically empathic.

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This episode takes on what is perhaps the most common, existential question of our time – how to follow your heart. Who doesn’t need a little help with that?

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This episode generated the most response the Dear Sugar inbox has ever seen – so much so that we followed it up with an episode on stepchildren.

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Fatherhood can be an incredibly complicated and painful topic. This episode may change your perspective on what it means to be a father and on the value of the father-child relationship.

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Perhaps not. Your jaw might be on the ground by the end of this episode.

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Weight is a controversial topic in relationships, and Steve and Cheryl end up having quite a passionate debate on the subject. This episode really shows how listening to others’ opinions on a subject can help us grow.

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The Sugars receive countless letters having to do with infidelity, and Esther Perel was one of the most insightful guests we’ve had on the show to date.

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Here, the hosts give briefer answers to a variety of questions, all centered around a theme. After this episode was released, several listeners wrote in with sentiments like, “I could have asked all of these questions!”