Docking Gatsby should’ve been a peaceful little “romantic sailing moment.” Instead, the wind turned it into a public trial, a line got eaten by the prop, and Rusty briefly became Captain Decorative while a marina audience silently judged our life choices.

In this Whole Damn Story episode, you’ll hear how Erica calmly stripped down, grabbed the rigging knife, dove under the boat like a lake-born Navy SEAL, and towed us back to the slip while Rusty considered a quiet career change. Mild profanity, maximum humiliation, and one clear lesson: don’t “get fancy” with the throttle.

Rusty still has the sailing bug. Erica still has the practical “and I have receipts” response. So naturally, they end up in Bocas del Toro, Panama—renting an open-air over-the-water house from Ruperto, an 80-year-old Italian artist who greets them in a weathered leather top hat like he’s the final boss of island charisma.

This place has no interest in your comfort lies: no glass, no screens, kitchen basically a “carport with a cutting board,” and a bathroom where modesty briefly visited… then moved out. And the whole house is drenched in Ruperto’s bold abstract paintings, like you’re sleeping inside someone’s imagination that has opinions.

Then Rusty spots it: a pagoda rising out of the middle of the sound—hand-built, stick by stick, accessed by Ruperto paddling a little John boat like this is just a normal Tuesday. (Meanwhile, Erica and Rusty consider opening a jar an athletic event.)

And because Ruperto is a storyteller, the night takes a turn into Atlantic crossings, a violently seasick hippie, a conveniently memorable topless detail, a squall that steals the mast, and—most devastating of all—Ruperto delivering the line that permanently upgrades Erica’s “hard no” on liveaboard life: “A sailboat is… an object of despair.”

Come for the tropical legend. Stay for the dream getting lovingly executed in one sentence

A sun-drenched day at Bora Bora Beach Club (the Colombian one, not the overwater-bungalow fantasy) turns into an unexpected ego event when two stunning women stroll up to Rusty’s cabana and ask one simple question in Spanish: “¿Estás solo?”

What follows is a messier, funnier, mildly off-color ride through retired-pirate energy, clicky-knee confidence, a barefoot victory lap to report the “news,” and Erica’s razor-sharp reality check. Under the comedy, it lands on the real point: aging isn’t about chasing youth—it’s about still feeling alive, seen, and surprised by your own life.