Gameplay: Diary of a Puzzle Editor
Plus, a conversation from the cosmic edge.
Gameplay
May 18, 2026

By Joel Fagliano

On a recent visit back home, I was digging through my childhood bedroom desk when I came across a tattered, spiral-bound notebook. Intrigued, I flipped it open, and was delighted to find the scrawled handwriting of my 18-year-old self, detailing my first summer spent as an intern for Will Shortz in 2011.

At the time, the internship seemed like a remarkable fluke, something I’d eventually look back on with fondness when I had a real job (“Can you believe that one summer I spent editing crosswords?”). I think that was why I decided to keep a journal in the first place, figuring this surreal experience would surely never happen again.

Turning through the pages, a youthful wide-eyed excitement radiates off the page. “I’m sitting here with a stupid grin on my face that won’t go away …,” the entry for Day 1 begins. I write about the nervous butterflies I felt upon arriving; the strange, curious puzzle museum that is Will’s house; and the jolt of delight that overcame me when I spotted one of my submitted puzzles on his living room table.

We spent most of the first day editing crosswords together. Spitballing clues with Will is described as “being put in a room with the Beatles and having to start jamming.” Somewhat embarrassingly, I wrote out a list of the clues that I had suggested and that he had liked — such gems as [Rocky start?] for GEO and [Response to the query “Does Mrs. Garbo fist bump?”] for NO GRETA SHAKES. Even typesetting the grids seems to have given me a thrill: “I’m writing the clues into the paper exactly as they’ll be seen by millions of solvers!”

To Will’s eternal credit, the sort of empowerment he gave to summer interns, making them feel as if their ideas mattered and their contributions were worth something, made a real difference in my career. Perusing the journal, I can see my confidence growing as the weeks went on — as I remark in a later entry, “I honestly didn’t think that I’d have this much sway!”

There are some very 2011 anecdotes. In one entry, I write about “teaching Will Shortz how to use Facebook.” In another, I’m asked to pause opening our mailed submissions with a letter opener because it was making too much noise for his NPR radio taping. Everything about that sentence feels like a blast from the past.

The journal is filled with nostalgic mementos. Paper-clipped to different pages are my first visitor’s pass to the New York Times office building, a yellowing themeless crossword of mine that ran that summer and a photocopy of an NPR on-air puzzle that the two of us wrote together at a diner after work.

It ends on a positive note: “Will offered me the internship for next summer! He said it’s been working out so well he’d be happy for me to do it again.” I coyly go on to say that I “haven’t decided yet,” but I’ll give you a little spoiler — not only did I go back, I’ve never had another job since.

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Column of the Week

This week, Nikita Richardson, who edits the “Where to Eat” restaurant newsletter, wrote: “Today’s puzzle had a few tough clues that were borne out in the solving, which made me eternally grateful for all the clues that surrounded them. A high tide, after all, lifts all boats.” Solve today’s puzzle, by Rena Cohen.

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