Overachiever Anna Shechtman had her first crossword puzzle printed in the New York Times when she was 19 years old. That’s, like, par for the course if you’re T.S. Eliot and, at 19, writing “The Love Song of J. Alfred Prufrock.” Compared to ordinary people, that’s stunning. At 23, she has graduated from Swarthmore (well hey there!) and is about to follow in the footsteps of James Franco by getting a PhD at Yale in English and Film. She has also been Official Puzzle Guru Will Shortz’s assistant and the intern for the Slate Culture Gabfest.
KATIE BARNWELL: When did you construct your first crossword?
ANNA SHECHTMAN: I constructed my first crossword right after I saw the movie Wordplay. I saw it when I was 14 and I had, I think it’s fair to say, my first moment of cinematic identification, which I probably should have been having with Drew Barrymore or Greta Garbo, but instead I had with Will Shortz and Merl Reagle. I was editing my high school newspaper at the time, so I started constructing puzzles for it. They were pretty bad! They were pretty topical, related to high-school gossip and the midterms that were coming up. I fell madly in love with this very niche pastime. …
That’s something he often asks me: “Is this a thing?” That one recently was actually HUMBLEBRAG. He asked me if it was “a thing”—it is indeed a thing, Will. …
I think he really values the fact that I have such a different frame of reference from him; he’s in his early sixties and from Indiana and I’m 23 and from Lower Manhattan. Despite our differences, he really does let me push back, and encourages me to, because I think he knows that the beauty of all crossword puzzles and, I think, the Times puzzle in particular, is that it is a democratic puzzle. Anyone can do it, everyone should do it, and so he wants it to appeal to as many diverse audiences as possible—and ideally, all diverse audiences. He has to appeal to me and my grandmother, and that’s a hard needle to thread, and I think that he does it really well.
Exercise caution reading while eating; the interview — as well as this one in the Times from 2010, when she first published a puzzle — may induce jealousy-related choking.
Photo via Horia Varlan