Photos by Noa Griffel   

Meet The 23-Year-Old Making the NYT Crossword Puzzle Cool

BY Katie Barnwell | Thu. May 29, 2014 | 12:00 AM | Culture Club
DIME, HUMBLEBRAG, JANSPORT, VALLEY GIRL. This list of words sounds like it was taken from Rihanna’s Twitter feed, but in fact, it’s a list of answers from one of Anna Shechtman’s crossword puzzles. The 23-year-old native New Yorker, who published her first crossword in the Times at just 19, has recently been injecting some swag into the traditionally conservative New York Times puzzle as editor Will Shortz’s assistant.

I first saw Anna at the American Crossword Puzzle Tournament in Brooklyn, when crossword-celeb Shortz summoned his assistant and the constructor of the tournament’s final puzzle onstage. To pretty much everyone’s surprise, out walked a pint-size stunner (or shall we say a dime?) with a refined yet humble vibe. In case you weren’t impressed already, the Swarthmore grad is heading to Yale in the fall for a PhD in English and Film, a program whose only attendee to this date has been James Franco (though we’re betting Anna won’t be spending her spring break in St. Petersburg).

For many, the New York Times crossword puzzle is vaguely known of: a niche hobby, perhaps something that you associate with your grandmother or that weird guy who sat behind you in math class. To others like myself, it’s simply “the puzzle”: the best part of the day. As I told a friend about this article, I explained: “If I had to choose between going out on Friday night or getting the Friday puzzle, I’d choose the puzzle every time.” (Though after six years, I can’t dependably finish a Saturday).

I met up with Anna at Bubby’s in Tribeca (which, she informed me, is open 24 hours and has the best pancakes ever), where we talked about OkCupid, ex-boyfriends, and shtupping––though not in the context of getting down so much as Across vs. Down.

Make sure to check out Anna's puzzle in today's New York Times. But if you're already a puzzler, beware: the following interview includes spoilers!

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.

I first saw your name at the top of Puzzle #7 at the American Crossword Puzzle Tournament. It was my and my friends’ favorite puzzle by far; we loved JANSPORT, had the standard mixed feelings about the Girls reference, laughed at the OkCupid clue, and wondered what it would be like to be a generation or two older and have to get DIME from the clue, “attractive female, in modern slang.” Tell me about your conversation with Will Shortz about this puzzle.
Yeah, I had the very unique, kind of surreal privilege of constructing this puzzle for the tournament. I came up with a theme and I had total free range in cluing until it was time for us to edit the puzzle together. I did have to sell Will on a few things. I had to sell him for sure on JESSA. With JESSA, I googled her and we watched some YouTube trailers for the upcoming seasons. For DIME, I explained to him the rough etymology; he knows about calling a girl a "ten,"—that’s inscribed in his slang dictionaries, of which he has probably five or six—and there’s not that big of a leap from calling someone a "ten" to calling someone a "dimepiece" to calling someone a "dime." I’m not sure that clue would have been able to run in the Times. I think he takes a few more liberties with the tournament, for obvious reasons.

It’s interesting to hear you say that he takes more liberties with the tournament than with the weekday puzzle. But actually, a few weeks before the tournament, my friends and I were discussing how surprised we were to see DOMINATRIX in a Saturday, and how, in general, there seems to be a recent shift toward being more inclusive of risqué and colloquial terms. Are you the force behind that shift?
I will definitely not take credit for more risqué or more youthful words appearing in the Times, but there definitely have been times when I’ve been able to persuade Will on something he didn’t think was crossword-worthy. It’s not always necessarily whether something is risqué, just whether or not something is mainstream enough or an actual phenomenon. 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.

His puzzle sometimes gets a bad rap for being a little prudish, you know, things need to pass the Sunday breakfast test: no URINE, no ENEMA—all those words have great vowels but they will never appear in a New York Times crossword. But I’ve been really surprised and thrilled by how open-minded he’s been. 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.

In an e-mail to me today you mentioned SHTUP, which you said was “Yiddish for bone, bang, have sex with, etc.”
[Laughs] Yeah, I called it Yiddish for bone, but more accurately it’s Yiddish for the verb “to stuff.”

One of the things that Will and I talk about a lot is the evolution of language. So it doesn’t just have to do with the evolution of the crossword puzzle. Yes, SHTUP probably wouldn’t have been in the crossword 30 years ago, for a number of reasons, one of which is that the puzzle itself (or the editor) was a bit pruder, but also because it has been normalized, neutralized. Rachel Maddow says it all the time on MSNBC; my Dad says it all the time and I think that that’s a generational thing—I’m sure his father wouldn’t have said it so casually.

At the tournament, Will brought you onstage and told the entire ACPT about your acceptances to multiple PhD programs.
Yes, he totally embarrassing dad-ed me! I was blushing so hard. But then afterwards, I can’t tell you how many mothers came up to me to tell me where their sons were going to law school or med school and tried to encourage me to pick that school. It was like, the most effective J-date I’d ever been on. It was pretty phenomenal.

My friend had one question: has anyone ever gotten laid at the ACPT?
Great question. I will neither confirm nor deny. I do know, actually, of two different couples who have gotten married based on meeting at the crossword tournament, so it is a little match box. Competitive crossword solving and also crossword devotion, fetishization, and adoration—that’s a unique thing, and so the people that congregate there, even if they come from really different backgrounds—Indiana and Tribeca—there is this common denominator which is extreme logophilia and nerdiness and a desire to have your wits tested, to be challenged, and it makes total sense to me that people would get married there. Now, whether they’ve gotten shtupped, I do not know.

No crossword-related interview would be complete without the question “pen or pencil?” But I feel like for us, the more relevant question might be, “iPad, iPhone, or print?”
I feel really strongly about the cleanliness of my grid. I don’t like when it looks like Tammy Faye Bakker has just rubbed her face on my crossword; that’s not a good look for me. So, I was really devoted to pencils for a while, but I got a lot of crap from my ex-boyfriend so I have converted to pens.

You do the Saturday in pen?
Well, I can no longer do the puzzle, which is the real sacrifice of my job, I will say. My mornings have gone from doing the crossword to now just reading about what the bloggers have said online about it, which is really kind of embarrassing.

But, also, I do have the app on my phone, obviously. I do have Across Lite on my computer, but if it’s easy, I will print it out.

Even though I am considered by some to be someone bringing youthful energy to the paper, I am a little bit anachronistic because I still construct puzzles by hand, because that’s the way Merl Reagle did it in Wordplay. I use grid paper and a dictionary, whereas most people use software. I’m not someone interested in big data and databases; I’m interested in literature and movies! But there was just a big article in the Philadelphia Inquirer about Bernice Gordon, who is 100 years old and is constructing crossword puzzles still. She uses software! So if she is, I don’t know why I’m holding myself back in the twentieth century.

Katie Barnwell works in data analytics in NYC and sometimes stays home on Fridays to do the puzzle.