Puzzling Origins

Just weeks after my graduation from Swarthmore, the postgrad gods gifted me an email from Will Shortz, crossword editor of The New York Times, asking me to be his assistant for a year.

I began writing crossword puzzles for my high school newspaper when I was 15. I was well suited to the medium, gripped by its logical and aesthetic challenges, and relieved to have a proper outlet for my propensity for bad puns. When I came to Swarthmore in 2008, my sights were never set on The New York Times—the gold standard of grids. I really wanted to construct for the Swarthmore Phoenix.

For two years, I wrote biweekly Swarthmore-themed puzzles for the paper. During midterms of my freshman fall, for example, I wrote a puzzle whose theme entries contained the word TERM in the “middle” of words: BUTTERMILK, MASTERMIND, LITTERMATE, etc. The campus’ endlessly initialized support systems (CA’s, RA’s, WA’s) provided ample fodder for a rebus puzzle, with KARA WALKER and CAMERA OBSCURA embedded in the grid. 

Convinced by my then-boyfriend that I could set my sights beyond the pages of The Phoenix, I submitted my first puzzle to the Times in the spring of my sophomore year. Originally intended for The Phoenix, it was a puzzle inspired by Swarthmore’s unofficial motto—emblazoned on sweatshirts in the bookstore—“anywhere else it would have been an A.” With the words GRADE INFLATION running through the grid’s center, the puzzle contained B’s that had been “inflated” to A’s to create punny phrases like HONEY COMA (“Result of a sweetener overload”) and LAMA CHOPS (“Monk’s karate blows”).

Will accepted the puzzle and rushed it to print. I was 19, and he wanted to place me on his growing list of published teenage constructors. I submitted puzzles for the next two years, and although I did meet Will once, when he spoke at Haverford College in my senior year, our relationship was mostly virtual: quibbling via email over the alleged “inelegance” of a grid’s southwest corner or debating the respective merits of UNDEROOS and MALE GAZE as puzzle entries.

Neither the most prolific constructor nor the fastest solver, I’m still not completely sure why Will asked me to work for him this year. I’m an outlier in the CrossWorld, a realm dominated by middle-aged men who tend to hail from the natural sciences. At Swarthmore, I wasn’t sure that anyone actually solved my puzzles until I took a class in the Science Center, where they seemed to be popular. They were left mostly untouched in the humanities hub of the Kohlberg Coffee Bar—where most of my closest, puzzle-indifferent friends spent their time.

That I am demographically rare among crossword constructors doesn’t explain why Will asked me to work for him, but it did make for a fruitful, albeit Odd Couple-y partnership: a 23-year-old English major from lower Manhattan and a 61-year-old puzzle titan from rural Indiana. Our debates about gendered language and American slang were intense—and often adorable. Is “fly” making a lexical comeback as a synonym for “cool?” Does anyone use “herstory” in earnest any more?

When I think about this past year working with Will—perfecting grids, writing clues, and preparing puzzles for print—I feel pulled toward saccharine sentimentality. In August I began a Ph.D. in English and film studies at Yale. Will watched me apply to graduate programs with, I think, a sense of quasi-paternal pride and total confusion as to why anyone would want to get a humanities Ph.D. He told me, “At Yale you’ll be so much closer to Stamford!”—the site of the 2015 American Crossword Puzzle Tournament. Needless to say, I’ll be there in 2015.