The 23-Year-Old Wordsmith Behind The Hip, New Voice Of The Times Crossword Puzzle

Thanks to Anna Shechtman, your clue for “bro” is no longer “sister’s sib.” It’s “Preppy, party-loving, egotistical male, in modern lingo.”

The 23-Year-Old Wordsmith Behind The Hip, New Voice Of The Times Crossword Puzzle
[Image: Flickr user Gwen]

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.

Anna Shechtman

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.

In addition to the standard assistant duties, like helping out with mail and sending rejection letters, the bulk of Shechtman’s day is spent cluing. Once a puzzle and its theme is accepted, out of the hundreds of entries each week, the two work in Shortz’s Pleasantville house to bring the grid up to the Times’ standards, she explained. “He’s a very hands-on editor, so he will actually make changes to the grid to make the words more worthy of a puzzle,” Shechtman told Fast Company. “From there, we’ll go on and change probably about 50% to 80% of the clues a constructor has written.”

The main goal is to get rid of crossword-puzzle-eze, words like “aria” and “ulna” that constructors use as crutches because of their letter combinations. (Vowels and consonant-on-consonant phrases prove extremely useful in grid construction.) Shechtman and Shortz weed out as many of the common words as possible, swapping them for more interesting words and phrases. The process often includes free association, the consultation of multiple dictionaries, including slang and niche dictionaries, and Internet rabbit holes–all in the name of finding a clever way to hint at a word or phrase.

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.

New York Times Crossword, May 29, 2014Copyright ©2014 “The New York Times Company.” Reprinted by Permission.

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.”


Shortz, who has worked at the paper for more than two decades, welcomes new language and cultural references. Crossword puzzles should reflect the way vocabulary and culture change, he says. “I’m completely in favor, and I think I’m relatively up-to-date myself–from movies, wide reading, and other ways,” he told Fast Company. “Still, 61 (my age) is different from 23 (Anna’s), and Anna does come up with great clues that I would never think of myself.” Shechtman recently suggested cluing “shane” as The L Word role for Katherine Moennig, rather than in terms of the 1953 Alan Ladd western, which Shortz usually uses. Shechtman also helps him discern if a trendy word deserves inclusion. Amazeballs, for one, did not make the cut.

In Shechtman’s puzzle, she wanted to use “Jerk, slangily” as a clue for “tool.” That got nixed in favor of “one being used,” in part, because of its vulgarity. Shortz tries to maintain a balance between including linguistic phenomena, without pushing people outside of their comfort zones. Words have to pass the Sunday breakfast test. “Urine” and “enema” have great vowels, but will never appear in the New York Times, Shechtman said. There are many other ways to clue “tool” without alluding to genitalia.

An incredibly well spoken 23-year-old who never used the throwaway word “like” in our conversation, Shechtman discovered her love of crosswords at the age of 14, when she first saw the documentary Wordplay. (Unbelievably, neither her lawyer dad nor art historian mom spent their Sundays with the crossword.) She identified with the people behind the puzzles, and wanted to create her own grid. Using a scene from the movie as a template, she started constructing for her Brooklyn high school’s newspaper. She soon discovered a crossword puzzle online subculture, and learned more advance creation skills. In college she was in charge of her school newspaper’s puzzle.

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.

New York Times Crossword, May 29, 2014. | Click to expand.Copyright ©2014 “The New York Times Company.” Reprinted by Permission.

“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 PhD 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.


Puzzle-doers, however, will likely feel her presence lurking in the clues for many crosswords to come. Shechtman, who lived in Williamsburg before moving back in with her parents in Tribeca, got Shortz to come to dinner and play ping pong in her Brooklyn neighborhood. (Shortz is an avid ping pong player, and owns his own table tennis club in Westchester.) “It was hilarious to watch him interact with Williamsburg,” she said. “He said to me: ‘I have so many new ways to clue the word ‘hipster.'”

About the author

Rebecca Greenfield is a former Fast Company staff writer. She was previously a staff writer at The Atlantic Wire, where she focused on technology news.