This Is Uncomfortable

Hard to believe, but we’re celebrating 10 seasons, and five years, of  “This Is Uncomfortable”! In this special episode, we’re pulling back the curtain to reveal the show’s origins, the biggest lessons Reema’s learned along the way and our favorite money tips from expert guests. Plus we’ll hear from you, our listeners, about the insights that have stuck with you through the years. 

Last spring, Jay Benedith and Ben Williams matched on a dating app and quickly hit it off. But just a few weeks into their budding romance, a Venmo request started to raise questions about their future together. What happens when your partner’s approach to money clashes with yours? Can nickel-and-diming jeopardize a connection? 

What does it mean to make a living from death? From a young age, Joél Simone Maldonado was fascinated by mortality, leading her to a career as a funeral director, embalmer and sacred grief practitioner. In the final episode of our miniseries on grief and money, Reema Khrais talks with Joél about her profession: the tough conversations around money, the toll it takes on her mental health, and why she advocates for more cultural competency in death care. Also, Joél offers tips to financially prepare ourselves for the inevitable, and Reema reflects on the personal impact of her recent experiences with loss. 

In the early 90s, Mike Perry found himself in a tough spot. He was living a carefree life when he was asked to take in a black mutt named Wisdom. What began as a reluctant favor evolved into something much deeper — a bond that would reshape Mike’s financial future, even long after Wisdom was gone.

This week, as part of our miniseries on grief and money, we explore how our love for pets shapes our financial decisions. Mike’s journey with Wisdom takes him from heartbreak to an unexpected windfall. And then later in the episode, we ask: is there such a thing as spending too much on our pets? Reema Khrais talks with Marketplace’s Kimberly Adams about the emotional and financial costs of caring for a beloved pet in their final days.