Crosswords are challenging fun for Winter Park’s Kristyn Dietrich 
By Leslie O’Shaughnessy
June 2009

From Palmer to Hillcrest and Canton to Palm there exists a common morning ritual at kitchen tables, on living room couches and backyard patios across Winter Park. Crossword puzzles have been a cultural phenomenon and an exchange of language, culture and information since they began in 1913.

For some it is a chance to challenge the mind; for others it is an opportunity to escape. There are those for whom it can even be an obsession. Among those with a wordy passion is Winter Park attorney and mother Kristyn Dietrich. A self-described “verbal person who enjoys words,” the 43-year-old has been hooked on doing puzzles since she was a young teenager. In 2006 after viewing the crossword documentary Wordplay at the Enzian Theater in Maitland, she was inspired to attend the American Crossword Puzzle Tournament depicted in the film. She has competed the past three years in the event that is considered the longest-running crossword puzzle tournament in the world.

“I had no expectations. I just wanted to see if I was in the competitive range,” she says with a smile. It takes a sharp mind to earn a law degree, and the Duke University graduate clearly has the chops. But it also takes a quick wit and strong communication skills to raise four children, all gifts that Dietrich uses in her passion for crosswords. In remembering her first day at the tournament she recalls, “The experience was intellectually stimulating, exhilarating and a rush in adrenaline.”

While some people stretch themselves with sports, art or music, the stretch for Dietrich happens in a Brooklyn hotel ballroom along with 700 other puzzle heads in the early days of March. The quest to solve a puzzle speaks to one’s ability to start with what you know and go from there. The more you know, the quicker you find answers – kind of like in life.

The American Crossword Puzzle Tournament officially begins on a Friday, but the real action starts Saturday morning. On game day, the ballroom at the Brooklyn Bridge Marriott is crammed with rows of tables with paper dividers separating the space between puzzlers. Participants are given their first of six puzzles of the day, with time allotments from 15 to 30 minutes per puzzle. A large clock on the wall keeps time. With the go-ahead, players turn over their puzzles and the air is filled with the sounds of scribbling. The fifth puzzle is the most wretchedly unsolvable for some. No blank spaces or mistakes allowed. Once a puzzle is finished, contestants raise their hands and judges pick up the puzzles, noting the time of completion. Participants then leave the room to fact-check and commiserate with their fellow puzzlers. The lobby atmosphere crackles like a family reunion with familiar faces that reunite every year. Some have become longtime friends through the event and their shared affection for filling tiny white boxes with exactly the right word.

“When it’s over, people are very supportive,” says Dietrich. “These are mostly personalities that are competing against themselves.”

On Sunday morning everybody is back in the room for one final puzzle, a 45-minute whopper. And then, based on the scores from Saturday and Sunday, nine players advance to the championship match made up of three contestants in three divisions. The sets of clues differ in each round and range in difficulty, although the puzzle answer words remain the same. The finals are staged in view of a live audience with the contestants – wearing headphones playing white noise – completing their puzzle with erasable markers on large white boards.

For the past five years, 24-year-old whiz kid Tyler Hinman of San Francisco has reigned champion. Hinman was the youngest to ever win, and he has mastered 40 tournament puzzles without an error. He presently works as an online operations associate at Google.    

“As a mom, I spend so much time worrying about my kids and their future, this is something I do for me,” says Dietrich, who maintains an online subscription to puzzles and buys puzzle books to practice. A problem-solver by nature, Dietrich says she’s doesn’t procrastinate, and she doesn’t do things halfway. “I enjoy when things come together,” she says - a rewarding byproduct for a crossword fanatic.

Dietrich has attended the past three tournaments accompanied by her mother and fellow crossworder Nancy Elliott. Now in her 60s, Elliott clearly relishes the annual trek with her daughter as the one time each year when it’s just the two of them. “It’s great that we have this common interest, and we both enjoy the challenge and seeing so many people with such bright minds. It’s thrilling to watch.”

The American Crossword Puzzle Tournament is the creation of Will Shortz, current editor of The New York Times crossword puzzle and whom comedian and crossword aficionado Jon Stewart has called “the Errol Flynn of crossword puzzling.” Also depicted in the film Wordplay, Shortz began making puzzles at 8 years old and became a phenomenon when he created his own curriculum and earned a degree in enigmatology, the study of puzzles, at Indiana University. Not unusual for someone who says his favorite word is “ucalegon,” which means a neighbor whose house is on fire. In 1993 he became puzzle editor at the Times, widely considered the gold standard of crossword puzzles. Shortz says he creates puzzles to “stretch people’s brains and bring them joy.” Attendance for the tournament jumped by a staggering 200 participants after the release of the documentary, Shortz says.

Margaret Farrar was the first crossword puzzle editor for the Times from 1942-1968. Farrar is credited as being the “First Lady of Crosswords,” as her efforts led to standardized puzzles. There do exist a few rules of design that are strictly adhered to in the world of crossword construction. There are no two-letter words used. There must also exist symmetry that if a puzzle is turned upside down the arrangement of black squares remains constant. Another implied rule requires that all puzzles must pass the Sunday morning “breakfast test” – no words pertaining to bodily functions are allowed. Puzzles are built by a constructor, who is the one to originate an idea for a theme around which they build the puzzle. Generally, a percentage of the words in the puzzle are related to the theme, the rest are arbitrary. The theme words provide the skeleton around which the puzzle is built and allow for the clever word play and mind banter that fans adore.

In The New York Times, Monday begins the week with the easiest puzzle, followed by days that progressively grow more challenging and culminating in the Saturday puzzle that is considered the most difficult. The New York Times Sunday puzzle remains the popular favorite, and while it is neither the easiest nor the most difficult, it is the longest puzzle and the one most fans look forward to completing.

There is something appealing about the idea of curling up in a bathrobe with a cup of coffee in one hand and the Times crossword in another that has been nurturing puzzle fans for decades. Mastering a puzzle takes finesse. “The more difficult a puzzle becomes, the more obscure, enigmatic and complicated the clues become,” says Dietrich. Generally, musicians and mathematicians tend to have an affinity for crosswords. The Indigo Girls are fans, as is former New York Yankees pitcher Mike Mussina, and former President Bill Clinton. Anyone wired for words, full of valuable and useless knowledge, both general and specific, as well as those with a keen sense of music, art, history, cartoons, television, politics or Greek mythology can excel. Then again, that is precisely the trick – there are no specific criteria or subject matter that give a puzzler an advantage.

A puzzler needs a wide understanding of all things. But for a mother striving to teach her children a love of language, the value of a good vocabulary and proper spelling, Dietrich’s passion provides a strong foundation:  “I think it makes me a better mom. My kids see me gain confidence through my accomplishments and they absorb this. They think it’s cool,” she says with a smile. This past year Dietrich finished 398th out of 674 contestants at the tournament, her quest to break into the top half thwarted, but her resolve to return next year more solid than ever. Her children will watch again as she continues to think before answering and reach again for the goal she desires. As a problem-solver, whether it be mastering a puzzle or confirming the details of her daughter’s Latin party at school, Dietrich continues to fill in the blanks with the right answer.