October 18, 2026
To: Todd Estabrook, Boston
From: Stephen Brown, Comfort Island
Dear Todd,
Yesterday we went to Clayton to witness a hugely popular event in the North Country- Punkin Chunkin. You should have been there.
Our friend Jeff Cole narrated the efforts of local construction companies who had created elaborate trebuchets and siege machines to toss pumpkins as far and high as possible into the St. Lawrence River. Each fall, thousands of people gather on the banks and docks and cheer them on.
The machines aren’t always successful. Pumpkins explode in midair, fly back towards the crowds or simply smash into the river. Some attempts are downright comical. But the crowd cheers anyway and every once in a while, a pumpkin sails perfectly up into the sky and lands far out into the water. These teams come back every year, because they love it.
Boats were tied up to the floating docks and about a dozen of our friends gathered near Campbell and Keiran’s new boat. You know, the regulars. We drank beer, ate chili, gossiped and talked about the end of the season.
It was damn cold and windy and because I felt like I had been herding cats all morning, I just couldn’t get into the spirit of things.
I’d raced to get out yesterday’s letter while doing breakfast and cleaning up. I pressed send and realized it was just an essay, not a letter, and not done with the usual care.
Later, our friend David approached me and said he loved my daily letters, but the morning’s post seemed different. Not as thoughtful.
It stung.
He wasn’t being malicious or thoughtless. But I felt like I’d let him down.
I think that one of my profound faults is being a perfectionist. I’ve honed that particular attribute over years in the entertainment business as a producer and executive. Unfortunately, it translates to my life at home. Forks in the wrong order, knives placed incorrectly, the wrong serving utensils- any of these annoy me to distraction. And people notice.
Last night I delegated setting the table for dinner. Brody wanted plates that could go in the dishwasher. It was make-your-own-pizza night, after all— there could be an informality.
I reluctantly gave in.
But when I went out to see how the group of young men was doing, I thought the table was a disaster. Why didn’t anyone see it? Why didn’t anyone care?
“For God’s sake,” I said, “you’re gay men, get it together!”
And the truth is, they cared. Just not as much as I did. Dinner could have been served on melamine or plastic and they would have been just as happy.
So who was I doing this for?
I think, ultimately, it’s for me. Hosting and creating a beautiful evening make me happy.
But does it?
When everyone else had gone to bed and I was doing a last pass in the kitchen, Conor and his friend Sebastian came down for a late-night snack.
I brought up the table-setting incident and Sebastian looked at it differently.
“Every ship needs a captain, and that’s what you do.”
They went off to bed. I finished the last dishes and took a long hot shower to wash off the day and reset.
I felt just a little bit better about the day.
Next year you and Henry have to stay at Comfort and join us. We really missed you.
Stephen