REGRET: July 2025 podcast playlist

Delve into the complex and often painful experience of regret and hear from experts who study it. Each episode explores how regret shapes our lives, decisions, and relationships through deeply personal stories, expert insights, and reflective conversations. From poignant tales of missed opportunities to interviews with psychologists on the science behind regret, this collection invites listeners to reflect on their lives and the moments that haunt them.

This playlist was curated with help from Jules, a member of the Chicago chapter.

Podcast Playlist on REGRET

Get the full playlist on your podcast player of choice using these platforms:

 
Hidden Brain: “You 2.0: Regrets, I have a few…” (August 2021, 29 min)
We all have regrets. By some estimates, regret is one of the most common emotions we experience in our daily lives. In the final episode of our You 2.0 series, we bring you a favorite interview with Amy Summerville, the former head of the Regret Lab at Miami University in Ohio. After years of studying this emotion, she says she’s learned something that may seem counterintuitive: regret doesn’t always have to be a negative force in our lives.
Nudge: “Dan Pink: “Here’s what you’ll regret when you’re older”” (September 2022, 32 min)
There’s one thing that almost all of us will regret. And we regret it more and more as we get older. In this episode with Dan Pink, author of NYT bestsellers Drive and When, we chat about regret, why you should have a bias for action and the world’s most regretful world-record holder. Oh, and you’ll learn why your gut instinct is statistically more likely to be wrong.
Heavyweight: “#18 Sven” (October 2018, 33 min)
Sven was on a jury that sentenced a man named Paul Storey to death. He’s regretted it ever since. Then, eight years later, Sven gets an email from Paul’s mother.
Happier with Gretchen Rubin: “440: Very Special Episode: We Talk About Regret—Our Own Regrets and Listeners’ Regrets” (July 2023, 38 min)
This episode explores the subject of regret. We talk about the
most common categories of regrets and why reflecting on regret can help us make our lives happier. We share some of our own regrets, and also listeners’ regrets.
Reply All: “#143 Permanent Record” (June 2019, 58 min)
This week, the most humiliating, unfortunate and regrettable things on the internet that simply will not come down. Also: the father who scours the internet for lost memories.
Bonus podcast episodes:

• Mindset Mentor: “The Regrets of the Dying” (June 2025, 17 min)
  Have you ever wondered what people regret most at the end of their lives? In today’s episode, I dive into the five most common regrets of the dying. I’ll share how these powerful lessons can help you avoid your own regrets and start living a life that’s true to you.
• Overthink: “Regret” (July 2023, 55 min)
  Coulda, woulda, shoulda… In Overthink’s long-awaited epsiode 82, David and Ellie fret over the meaning of regret, in everything from life-altering career decisions to sloppy teenage breakups. They consider the usefulness of regret — if it has one at all — and explore its relation to a life well lived, investigating its philosophical lineage from Confucius and Aristotle to today. Can 20-year-olds regret? Can dogs? Is regret ever rational? And, when does remorse turn into existential despair?
• Help Me Be Me: “Ep 212: Self-forgiveness – Releasing a regret you are holding onto” (December 2023, 48 min)
  This is for anyone who is holding onto a regret or pain that affects their identity in the present: something that you do not want to take into the new year. When something is bugging us about the past, we are really just pausing a part of the present and living through a warped memory. Sometimes that is because we feel that this will somehow give us what we deserve, like an unconscious act of penance. And sometimes it’s because we are twitching around this thing– almost like a muscle spasm. When we just can’t seem to face a regret in an objective and open way, we cannot process and release it.
• Nudge: “Dan Pink: “No regrets? That’s bullsh*t”” (September 2022, 28 min)
  Three types of people live a life of no regret. Children, the mentally ill, and liars. 99% of us have regret, but for good reason. Regrets help us. Today, Dan Pink, best-selling author of Drive and When, explains why regrets are good for you, how to negotiate better, and the golden rule for living a happier life.

Conversation Starter Questions:

1. What’s one regret you’re comfortable sharing—and how has your perspective on it changed over time?
2. Do you think regret can be a useful emotion, or should we try to let go of it entirely? Why?
3. Which do you find yourself regretting more: things you did or things you didn’t do? Why do you think that is?
4. In Happier, Gretchen Rubin talks about “category regrets”—relationships, education, travel, etc. Which category seems to hold the most weight for you?
5. How do you define the difference between guilt and regret? Did any episode shift or clarify that definition for you?
6. Hidden Brain introduces the idea that we often distort memories when we regret. Have you ever realized a regret wasn’t as clear-cut as you once thought?
7. After listening to these episodes, do you feel more motivated to take action now to avoid future regret? If so, what’s one thing you want to do differently?
8. How do culture, age, or personality shape the way people experience and express regret? Which episodes offered perspectives you hadn’t considered before?