Check your Venmo, please

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.  We’ll be back with a new season in 2025! For special content and updates on what’s next, subscribe to our newsletter. 

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?  If you liked this episode, share it with a friend. And to get even more Uncomfortable, subscribe to our newsletter!

This week, we’re sharing an episode of another podcast we think you’ll love. “Notes From America With Kai Wright” is a show from WNYC Studios about the unfinished business of our history, and its grip on our future. In this episode, Wright interviews choreographer Bill T. Jones about his groundbreaking dance performance “Still/Here.” Jones shares his reflections on creating such an essential piece of performance art amid the AIDS epidemic and while grieving his own partner, what he learned from spending time with the “survivors” who inspired it, and how “Still/Here” has evolved for a new generation of audiences. To get even more Uncomfortable, subscribe to our newsletter!

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.  If you liked this episode, share it with a friend. And to get even more Uncomfortable, subscribe to our newsletter!

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. If you liked this episode, share it with a friend. And to get even more Uncomfortable, subscribe to our newsletter!

While sorting through her father’s belongings after his death, Amanda Petteruti came across a collection of locked toolboxes. What she discovered inside made her rethink what she knew about her family’s finances and left her with unsettling questions about her dad: Why had he spent so much money on this secret hobby? Why was it now Amanda’s burden to handle? And how do you find closure with someone once they’re gone?  This episode is the first of a three-part miniseries exploring the intersection of money, grief and loss.  If you liked this episode, share it with a friend. And to get even more Uncomfortable, subscribe to our newsletter!

This week, we’re revisiting one of our favorite episodes and reconnecting with old friends for an update. Rebecca Danigelis never planned to stop working. She was an executive housekeeper in Boston raising two kids as a single mom, and everything she earned went to making sure they got the best education she could afford. When her son Sian-Pierre was climbing the ranks as a journalist and entrepreneur, it seemed like all the overtime, frozen dinners and sacrifice were worth it. But just as his career was taking off, hers started to crumble. We first aired this episode in 2022, and now Reema checks in with Rebecca and Sian-Pierre to see how their financial situation has unfolded. If you liked this episode, share it with a friend. And to get even more Uncomfortable,  subscribe to our newsletter!

Nikki Massie never had a reason to question her salary. After more than a decade with the same company, she’d earned awards, promotions and the trust of co-workers who felt like family. But then one day, she discovered she might have missed out on tens of thousands of dollars over the years. Nikki began to wonder: What do you do when you suspect you’ve been underpaid? And at what point do you consider walking away?  If you liked this episode, share it with a friend. And to get even more Uncomfortable, subscribe to our newsletter!

As we reflect on 10 seasons of “This Is Uncomfortable,” Reema shares a snippet of a conversation with the show’s founder-producer, Hayley Hershman, about what they’ve learned from making the show and how their relationships with money have changed over the years. And we want to hear your thoughts, too! What’s something you’ve learned from listening to “TIU” over the years? You can tell us how your relationship with money or work has changed, or maybe what the show has made you think more deeply about. Record a voice memo and email it to us at [email protected]. Or you can call and leave us a message at 347-RING-TIU (347-746-4848). Either way, be sure to include your name and where you’re calling from. There’s a good chance we’ll include it on the show!

Sisters Brittany Walsh and Nicole O’Neil have always been close. But when Nicole started experiencing mysterious health problems, her turn toward alternative treatments divided them. As Nicole spent more and more money on dubious cure-alls, Brittany was faced with a question: What do you do when you’re afraid the person closest to you might be losing themselves?  If you liked this episode, share it with a friend. And to get even more Uncomfortable, subscribe to our newsletter!