Dear Sugars

Cheryl Strayed and Steve Almond co-host Dear Sugars, which grew out of Strayed's beloved Dear Sugar advice column and has been running as a podcast since 2014 through WBUR. The format centers on listener letters -- people write in about relationships, identity crises, grief, family ruptures, and the specific ways love gets complicated -- and the hosts respond with what they call radical empathy. That is not a marketing phrase. Strayed and Almond genuinely sit with difficult questions instead of rushing to tidy answers, and they regularly bring in guest experts when a topic calls for specialized knowledge. Episodes run 24 to 50 minutes and drop biweekly, with recent seasons mixing new episodes and rewind installments that revisit earlier conversations. The show has 403 episodes, a 4.5-star rating, and over 5,600 reviews. Strayed brings the literary sensibility you would expect from the author of Wild, while Almond adds a self-deprecating humor that keeps the show from becoming too heavy. The questions are not always about romantic love -- some are about loving a parent through addiction, or figuring out how to love yourself after a major loss. That breadth is part of what makes it special. If you want advice that treats your problem as genuinely worth thinking about, rather than something to be solved in a hot take, Dear Sugars is the standard.