I'm standing in the pouring rain at the corner of Hudson and Morton Streets in the West Village with my umbrella awkwardly tucked under my left arm, Wednesday’s New York Times, folded in fourths in one hand with the morning’s crossword puzzle face-up and a blue pen in my right. I am late for work but I don’t care. I cracked the theme of the puzzle several minutes before on the train and unlike my usual routine, I am unable to put it away for the duration of my 10-minute walk to work. I am determined to finish it right then and there, pouring rain and tardiness be damned.

It’s late spring 1994, I’m 22 years old and en route to what was then my first job. I had only started doing puzzles two years ago in college and was giddy about the prospect of completing a mid-week puzzle. [Note: The New York Times’ Crossword Puzzle gets progressively harder each day after Monday, with Saturday being the hardest.] Still ensconced in that collegiate slacker mentality, I had yet to shake hands with the real workaday world. Hence, my priorities: puzzle first, work second.

Soon I sense a pair of eyes burning through the back of my paper. I look up and see a petite older woman in a nylon tracksuit with her tiny pert dog on a leash, staring at me. The woman is smiling. I smile back and shrug. "Hey, sometimes you gotta do what you gotta do," I say. She laughs, making her way over to me.

Trying to step in close to me, in spite of the distance imposed by our two umbrellas, she peers over my shoulder and says, "Oh, you’re doing a good job. You’ve got them all right so far."

"Thanks," I reply. "I’m pretty psyched that I figured out the theme, actually. Now it’s just a matter of filling it all in."

"Yeah. That is a nice feeling, isn’t it?"

I continue to fill in more squares when she says, "You know, I’m wondering, being that you’re a twentysomething and all, I’d love to know what you think of the Times’s new editor, Will Shortz?"

With all the enthusiasm my body could muster that raw, chilly spring morning, I look up and say, "Will Shortz? He’s amazing! He’s the Tina Brown of crossword puzzles! He bulldozed his way in there and has made The New York Times Crossword Puzzle accessible to a lot more people. Younger people especially."

What I was referring to was Shortz’s introduction of two milestone features, the first being clues that refer to popular culture, including brand names. I loved it! My father, a master puzzler with several decades experience, was now calling me for answers. He once called me to ask who Fred Flintstone’s best friend was and which band sings "Losing My Religion." I would give him hints until he figured it out. He always made me sweat it out when I asked for help, so why shouldn’t I return the favor?

Shortz’s other introduction was a great coup to all those puzzle constructors who had, until then, remained anonymous. Thanks to Will Shortz, cruciverbalists’ bylines began to appear on the bottom left-hand side of every grid, an addition that was appreciated by constructors and solvers alike.

Tina Brown, who had taken over The New Yorker less than two years prior, had introduced a few things to the legendary literary magazine that ruffled many feathers, but perfectly preened mine. Akin to The New York Times’ objective, Tina’s mission was to make The New Yorker appeal to a younger, hipper audience. Tina had her detractors, as the one-person buzz factory always will, but she unequivocally upped the ante at The New Yorker by including bylines in the "Talk of the Town" section and inserting provocative subheads to better draw people—twentysomethings with short attention spans—in. It worked for me. I was much more interested in reading The New Yorker than I had been pre-Tina when I read it mostly for the cartoons.

The woman smiles again and says, "Wonderful! Great to hear. I’m sure Will will love to hear that."

My jaw drops and my eyes bulge.

"You know Will Shortz?" I ask.

"Yeah, sure. I’m a puzzle constructor myself. I also wrote a book about him. He’s a good friend of mine."

I lunge for her arm and say, "You must introduce me to him. I mean, I’m a huge fan of his. Huge!"

She laughs at my effusive request. After a moment of silence she looks at me and says, "Actually, I’m having a cocktail party next Thursday and Will will be there. Would you like to come?"

"Absolutely! Tell me when and where and I’ll be there."

She introduces herself as Helene Hovanec and takes down my number. I make sure to take her number too to deflect any potential blow-offs or negligence on her part. After she tells me about her two nice Jewish sons, one of whom, she points out, is single, I calculate that she’s probably my mother’s age. We say goodbye and I hurry the rest of the way to work.

The next day Helene calls and gives me her address, which not surprisingly, was right around the corner from where we met. She informs me the party starts at 7:00 and that she hopes to see me there. "Can’t wait," I say.

Thursday morning of the following week I dress for work with extra care. So, I thought, what does one wear to meet the Crossword Puzzle Editor of The New York Times? A little black dress? Nah, too sexy. Jeans and a T-shirt? Uh-uh. Too informal, plus it hints of disrespect. Hmm. Something casual yet funky, but not too over the top. I settle on an olive suede tank top I bought at a flea market in New Zealand, a long flowy white skirt and a pair of open-toe sandals with a mini-wedge heel. I look at my clock and think, Cool, only 11 more hours till I meet the Puzzle Master himself.

Lest you are unaware, earning the title of New York Times crossword puzzle editor is no easy feat. You pretty much have to wait for the reigning one to die. Prior to Will Shortz there were only three other editors in the puzzle’s 51-year history. The first one was Margaret Farrar who started editing the puzzles by default. She was an executive secretary to one of the honchos at The New York Times and noticed that there was no formal editing process for the puzzles before they went to press. So without being asked, Ms. Farrar took on the additional task of filling them out to check for any inconsistencies or errors.

In 1969, more than a quarter-century later, Ms. Farrar left to edit The Los Angeles Times’s puzzle and Will Weng took over her editorship. Having been born in 1971, I had never done one of Will Weng’s puzzles during his nine-year tenure, although I have heard that Weng had a wry wit and his puzzles were void of references to popular culture. When Weng died in 1977, editor number three, Eugene T. Maleska, stepped up to the plate. Anyone who has done a Maleska puzzle knows how esoteric they were. He loved to infuse them with uncommon Latin words and phrases – i.e., they were ball busters. They left my palms perpetually sweaty and my teeth gnawing on pen caps. According to the Times’ website, Maleska was "a poet, educator, Latin expert and opera buff." Although I’ve never wished any dead person ill, I was pretty glad to have him out of the editing throne and hoped I would take more kindly to his successor.

The person responsible for finding Maleska’s replacement was Jack Rosenthal, the then editor-in-chief of The New York Times Magazine. And in making this decision, he set forth one criterion that was new to the position. He wanted someone who could connect with a younger generation. The search lasted two and a half months. For the millions of obsessed puzzlers across the land, those 10 weeks were fraught with fear and excitement. Who would it be? Would he make any profound changes to the current format? Would he be harder or easier than Maleska? Would he be a she? On November 21, 1993, the baton was handed over to Will Shortz, the editor of GAMES Magazine for more than 10 years.

Mr. Shortz had been on the job for less than a year when I came to meet Ms. Hovanec on the corner of Hudson and Morton. And in that short, soggy exchange, I was somehow dubbed the voice of my generation, an important responsibility that I wasn’t about to take lightly.

I show up at her spanking-new high-rise on Hudson Street. It was a medium-size red brick high-rise with gleaming windows trimmed in forest green. After her doorman buzzes me up, I ring Helen’s doorbell and am greeted with a big hug and kiss. The first thing I notice is that I’m overdressed. Helene is wearing shorts and a casual short-sleeved blouse. There’s another couple in their late 30s, early 40s, on the couch wearing shorts, T-shirts and walking sandals. And then there’s Will in a short-sleeved button-down shirt, khakis and brown oxfords. And that’s it. No one else.

"How many more people are you expecting," I ask.

"This is it," Helene says clapping her hands together to indicate finality.

"Cocktail party?" I think to myself. Is this what I have to look forward to as an adult? To me, this feels like having a few friends over to watch Seinfeld and order-in Chinese.

I settle in and Helene introduces me to Will and the other couple, a husband and wife from the Netherlands, who, apparently, were the crossword puzzle editors of Holland’s’ largest newspaper. I didn’t know what to make of it except that the puzzle community sure seemed tight-knit. I had never seen a picture of Will and didn’t really know what to expect. I guess you could say that he’s probably how you’d picture a man who makes his living creating and editing crossword puzzles. He isn’t particularly handsome, but he’s not ugly either. He has straight brown hair parted a bit to the side and a thick brown mustache. He is somewhat fair-skinned with brown eyes. His look is that of a geek who could care less that he’s characterized that way, as he’s too busy being the master of his own—if peculiar—domain.

Will is fairly enthusiastic about having a young person there to tell him how he’s faring with Generation X. Excitedly I tell him how my father calls me now for puzzle advice and how much I love that role reversal. I tell him that I can now get through Monday’s and Tuesday’s puzzles, but that Wednesdays and beyond are still a challenge. I tell him I like his puzzles a hundred times more than Maleska’s.

Eventually we get deep into conversation about puzzles and words. Puns and anagrams start flying about the room, each of us trying to outwit the one who quipped before. I want to appear clever to impress this room of puzzle aficionados, but too many letter combinations are ricocheting about my brain and I can’t seem to grab hold of any of them. Suddenly, Will picks up a cocktail napkin and starts writing.

"What are you doing," I ask.

He just smiles and keeps writing.

I pick it up and it reads: T. Eliot, top bard, notes putrid tang emanating. Is sad. I’d assign it a name: gnat-dirt upset on drab pot toilet.

"The world’s longest palindrome," says Will.
It’s worth mentioning that Will scribbles this completely from memory. Before I have a chance to bask in his nerdy, wordy brilliance, he picks up the pen and begins writing again.

This time he writes "Pneumonoultramicroscopisilikovolcanocoriosis," the longest word in the English language. Again, by rote. "It means miner’s black lung disease," Will says. And then, with a chuckle, he tells me that there are some words in existence that we’ll never have any use for, like, "ucalegon," which refers to the first person seen after a house is on fire.

I am wowed. In every way possible I am in awe of his easy brilliance, his passion for language, his encyclopedic knowledge of, well, just about everything. I too love words and the manipulation of them, and there I am sitting next to—conversing with!—one of the world’s masters.

Helene announces that dinner is ready and we all head over to her round kitchen table.

"I hope you don’t mind," she says, "but we’re using paper plates."

Next thing I know she puts a big bowl of ziti mixed with red tomato sauce in the middle of the table. "Dig in," she says.

I certainly learned a lot of new words that day. But I also learned a definition for a word I thought I already knew: cocktail party.

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