5 Questions with Dave Barry

5 Questions with Dave Barry

Author: Paul Ollinger May 28, 2026 Duration: 30:52

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Oh my goodness what a fun time I had chatting with Dave Barry on the first episode of 5 Questions, my bite-sized, live-streamed Substack interview show that I’ll be producing in addition to longer-form episodes of Reasonably Happy. Dave’s column was syndicated to hundreds of newspapers around the globe for several decades. He has published dozens of books on myriad topics that sold millions of copies—of books, not topics—in 22 languages. The New York Times called him “the funniest man in America.” (And when has the NYT ever been wrong?) In other words, he’s accomplished an incredible amount in the funny game, and I'm thrilled I got to talk to him. In this fast-moving 30 minute conversation, we talk about:

• What he’s looking for in a nursing home.

• Advice for me on shepherding my kids through the college search process (even though it doesn’t matter where they end up)

• The rock band he plays in with Stephen King, Amy Tan, Roy Blount, Jr., Scott Turow, and many other

• Which other authors make him laugh

• What Baby Boomers could learn from Gen Z (and vice versa)

Listen now and share with all your friends! Also, come see me tell jokes (or give a talk), in person:

* June 4 - Atlanta Athletic Club

* June 5 and 6 - Laughing Skull Lounge, Atlanta

* June 12 - Wade Hampton Country Club, Cashiers, NC (Talk)

* June 19 and 20 - The Comedy Catch, Chattanooga

* June 25 - Happy Couples Show, West Side Comedy Club, NYC

* July 21 - The Venice West, Los Angeles (on sale soon)

* July 23 - Cobbs Comedy Club, San Francisco

* Aug 1 - Sticks and Stones Comedy Club, Southampton, NY

* Aug 8 - Atlanta Country Club

* Aug 13-16 - McCurdy’s Comedy Theatre, Sarasota, FL



Get full access to Reasonably Happy at words.paulollinger.com/subscribe

Paul Ollinger has worn a few different hats-stand-up comedian, tech executive, and now, the curious host of Reasonably Happy with Paul Ollinger. This isn't a lecture series or a dry self-help guide. Instead, it feels more like pulling up a chair for a series of genuinely engaging talks that wander into the places where our daily lives, careers, and inner worlds collide. The conversations, which feature authors, thinkers, and various creatives, are refreshingly candid. They dig into the practical and philosophical questions about what it actually means to build a life that feels both successful and satisfying. You'll find that each episode of this podcast approaches big themes-money, purpose, and the pursuit of contentment-with a blend of wit and thoughtful depth. The underlying idea isn't about finding a perfect, Instagram-ready version of happiness, but something more grounded and attainable. It's for anyone who's ever wondered if there's a smarter, more meaningful way to navigate the pressures of business and culture without losing sight of what matters. Tuning in, you get the sense that Paul is figuring it out alongside his guests, making the insights feel earned and relatable. The result is a consistently interesting exploration of how we can all aim for a life that feels reasonably, and authentically, well-lived.
Author: Language: English Episodes: 50

Reasonably Happy with Paul Ollinger
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