Anna Shechtman '12: The Hip, New Voice Behind The Times Crossword

Fast CompanyThe 23-Year-Old Wordsmith Behind the Hip, New Voice of The Times Crossword Puzzle

The answers to the May 29th New York Times crossword puzzle included "epicness," "twitter hashtag," "where it's at," and "hell no." Although the 61-year-old Will Shortz edits every single submission that graces the Gray Lady's pages, that day's entry (a Thursday) had sprung from the mind of 23-year-old Anna Shechtman, Shortz's assistant and a four-time puzzle contributor for the Times.

Since starting at the Times straight out of Swarthmore College last year, Shechtman has brought some youthful edge to the 72-year-old quadrant of the paper. Not only did Shechtman get Shortz to include clues like "State of being awesome, in modern slang" (answer: epicness) in her own puzzle, she has influenced dozens of other grids, helping to justify more modern words and clues.

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The best puzzles make people smile. "A constructor's dream is to have a solver have a delayed or belated 'aha' moment, something like an 'Oh!'" Shechtman explained. For anyone who has figured out the gimmick to a crossword, you know the feeling she is talking about - that moment when you get the hidden theme or joke.

For her recent Times puzzle, for instance, Shechtman used the theme "sharp." The clues "#1," "#2," "#3," and "#4," all had answers whose shapes - much like the accidental used in musical notation to indicate a sharp note - are also pound signs, like the Twitter hashtag or a tic-tac-toe grid. "Just had the biggest 'Ohhhhhhhh...' moment I've had in a long time," puzzle reviewer Rex Parker wrote that day on his blog, where he solves the Times crossword and reviews it every single day. "Aha" moments can also happen on a clue-by-clue basis. "Bubblewrap" for "It might pop in the post office," for example.

In helping Shortz create more "aha" and "oh" moments, Shechtman has brought both a youthful and female perspective to the puzzle. By watching the trailer for Bad Neighbors and YouTube clips of How I Met Your Mother, Shechtman recently got Shortz to change the way he clued "bro." He usually goes with something like "sister's sib." "I think the word has come to mean a lot more. It's loaded with a lot more cultural significance than that," she said. In a February puzzle, the clue read: "Preppy, party-loving, egotistical male, in modern lingo."

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At 19, the Swarthmore sophomore got her first puzzle in the New York Times, the 20th teen ever published in that section. That's when she first developed a relationship with Shortz. He mentored her through the second puzzle she sent in the next year, helping her make her southwest corner more elegant. They met in person when he spoke at nearby Haverford College; he gave her a shout out as a constructor in the audience.

"Then randomly, really, really randomly, it was the loveliest, most random email, he asked me if I had anything to do next year," Shechtman said. Shortz says there was nothing random about his inquiry. He had been impressed by her work and knew of her impending graduation. Shechtman did have plans; she had been accepted to a French literature master's program at the Sorbonne. She opted to work with Shortz instead. "It seemed too interesting of an experience to pass up," she said.

After a year of cluing, Shechtman is preparing for life beyond the puzzle. In the fall she will head to Yale for a dual Ph.D. program in English and film. She doesn't want to be the next Will Shortz, but she hopes to continue working with him and the Times. This year she helped organize the American Crossword Puzzle Tournament, even writing one of the puzzles, which included "Jansport," "Jessa" (from Girls), and "humblebrag" among its answers. ...

Shechtman graduated as an honors English literature major with minors in art history and interpretation theory from Swarthmore. She had her first crossword puzzle published in The New York Times in 2010, becoming the second female crossword constructor under 20 ever published in The Times. At Swarthmore, Shechtman worked for War News Radio and wrote puzzles for The Phoenix