Pleasure & Regret: Gibran, Hedonism & the Night I Regret

At the end of the last episode, I kept saying one word. Permission. Permission to play.

And I realized I never asked the next question. What happens when you give yourself permission… and you regret it?

So in this episode I tell you two stories. The first is a night in my thirties, new to drinking and new to a lot of things, when I let myself step into the middle of someone else's relationship. I didn't ask. I didn't care enough to ask. That's the story that still gives me a twinge.

The second is a pleasure I was told I should feel guilty about, and didn't.

Holding them side by side is Kahlil Gibran's poem "On Pleasure," from The Prophet. It's a hundred-year-old poem that calls pleasure a freedom song, but not freedom. That asks whether a firefly could ever offend the stars. And that has a line about regret so close to my own story it stopped me cold.

Along the way: why I grew up hearing that hedonism brought down Rome. Whether chasing pleasure on purpose is actually a better way to live. Why getting experience late doesn't mean you missed it. And the question I keep coming back to: when we regret a pleasure, is it really the pleasure we regret? Or who we were being when we had it?

I don't land it. I rarely do. But I think regret might be information, not punishment. And not every rule deserves your guilt.

Stay after the goodbye. I read the whole poem.

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