Will Shortz: Crossword Tips…and the One Puzzle He Can’t Solve

As a puzzle-obsessed child, Will Shortz’s father gave him some sound advice: “Puzzles are an avocation, they are not a vocation.”

Had he followed that advice, The New York Times crossword editor would likely be someone else altogether.

Instead, Shortz’s love of puzzles led him not only to edit one of the most popular sections of the newspaper, but also to amass a collection of historic puzzles, which he says is the largest in private hands.

Shortz said his love of letters and words – his favorite letter is Q -- was inspired by his mother who was a writer. And his childhood hero was not Superman or the Lone Ranger, but Sam Lloyd, a puzzlemaker of the early 20th century.

Shortz created his first puzzles at age 8 and then sold one to a puzzle magazine at 14, becoming a regular contributor two years later. He is the only person in the world to have a college degree in enigmatology (his thesis was on the history of American word puzzles before 1860). Not believing he could make a living at puzzles, and still thinking of his father’s advice, Shortz followed it up with a law degree from the University of Virginia. But he never practiced law. Now, in his 20th year as crossword puzzle editor at the Times, he selects and edits puzzles from puzzle-makers all over the world.

“The process of creating a crossword is exactly the opposite of how you solve it,” explained Shortz. “If you're making a puzzle, first you think of your theme. You put your long answers in the diagram. They have to be symmetrical and put in symmetrical positions. Then you construct a grid with as good vocabulary as you can. And when you're done you write the clues.”

Though crosswords are no longer created by hand, the old-fashioned way on graph paper, Shortz still edits print-outs of the puzzles with pencil, substituting words or rewriting clues to adjust the level of difficulty.

Shortz offered three tips to solving a crossword:

--- The New York Times crossword gets harder as the week goes on. Monday is the easiest. It builds up to very hard on Friday and Saturday. Sunday is larger but it's more like a hard Wednesday or easy Thursday in difficulty. “If you're doing your first crossword, start with a Monday. See if you can do it. And if you like it and if you can, then see how far through the week you could go.”

--- Fill in whatever you know for sure. Look through the clues and find the first one that you're sure about. “And then take the unusual letters and work from the crossings. A ‘B’ is a more distinctive letter than an ‘A.’ So see if you can work off from the B and get the crossing answer. Build out from what you know.”

--- If you get stuck, sit back and take a fresh look at the puzzle. “Often you'll get one new answer and then you're off and running again.”

But being a crossword editor is not the only thing Shortz is known for. He has a weekly gig on National Public Radio, directs the annual competition of the American Crossword Puzzle Tournament and was featured in the 2006 documentary Wordplay along with some of his biggest fans, including President Bill Clinton and Jon Stewart.

At his home in Pleasantville, N.Y., a handcrafted cabinet contains some of Shortz’s collection of historic puzzles, including the very first crossword puzzle ever created: the “word-cross” game in a 1913 supplement of Fun in The New York World, a long-defunct newspaper. Shortz’s office is full of reference books – from the dictionary to the Bible to The World Almanac. Nearby, the master bedroom was converted to a library holding his vast collection of historic softcover and hardcover puzzle books.

An unsolved Rubik’s Cube hints at a puzzle Shortz said he cannot do: “I’m good in two dimensions. I can slide blocks around, but in three dimensions, my mind just doesn’t work that way.”

But puzzles do not take up all of Shortz’s time. As a child he played Ping-Pong and then won trophies in high school. That early hobby became something of an obsession in adulthood. He now owns the Westchester Table Tennis Center in Pleasantville. Shortz has challenged himself to play every single day this year, recording it on camera for a few minutes as proof.

“Table tennis is a brain game just like puzzles,” said Shortz. “So they go together in a weird way. In each case, whether you're solving a crossword or playing table tennis, you get completely wrapped up in this activity. I don't do a lot of crosswords for fun because that's my business. So I play table tennis and it blocks out the rest of the world. When I'm done, I'm ready to go back to everything.”

Shortz said “practically everything in the world can appear in a crossword” though not without difficulty.

“I'll tell you the one that has killed me, it's Lorena,” said Shortz. “It's a fairly common woman's name, L-O-R-E-N-A. It has come up in crosswords before. But there's only one famous Lorena. She's the one who excised part of her husband's anatomy. And that's not something I really want to use in a crossword.”

ABC News' Brian Fudge and Henry Gretzinger contributed to this episode.