New York Times, Monday, September 21, 2020

I had been thinking about starting a crossword club for a while. Then the pandemic struck. When I heard about the Wave Learning Festival, a student-run initiative whose stated goal is to combat the educational inequalities that the pandemic has only exacerbated.

I applied to teach a course on crossword construction. Fortunately, they specialize in offbeat topics that might be offered at universities, but rarely show up in a school classroom.

My class consisted of about a dozen people. We met online three times a week for three weeks. I tried to make it as interactive as possible, with students constructing word squares in the first class. We ended the course by constructing a whole puzzle together. It was rejected. The New York Times had already accepted a puzzle with the same theme.

I enjoyed the experience, so I decided to sign up to teach the class again. The second time went more smoothly. We solved quite a few puzzles together. That gives you an appreciation for what goes into a good crossword. It was extended to ten classes, giving us time to cover all the fundamentals. We were thrilled when the editorial team accepted our puzzle.

Our theme started with a discussion of Mexican food. We were thinking about the ingredients of nachos and noticed that chips and dips rhymed. That got us thinking about rhyming phrases. We needed another wrinkle and thought that if the phrases themselves rhymed with each other, that would be pretty cool.

We needed to start with a word that had as many rhymes as possible. NIGHTLIGHT led us to try "-ite", which also has an unusually large number of 1-syllable rhymes. Even so, it was unclear whether there were enough such phrases to make a crossword.

There was a fairly intense debate about the final selection of our theme answers. Was it a problem that we had both "night" and "knight"? We could have gone for a different set of theme answers that would have instead included KITEFIGHT and LIGHTBITE. Ultimately, we liked the overall quality of this set enough that we were willing to overlook the whole night/knight situation.

This was a great experience for me, and I hope the class feels similarly!

A couple of years ago, a crossword-solving friend of mine who's a "10x engineer" at Google innocently mused that most of crossword-making should be automatable.

"Ah, young padawan," I said in a terrible Yoda accent. "But a theme how about? A novel idea, AI cannot generate, hmm?"

"It can't be that hard," he said. "How about ... KING KONG, PING PONG, DING DONG …" He cleared his throat. "MING MONG? Is TING TONG a thing?"

"SING SONG," I added. "But would you have fun solving such a simple rhyming puzzle?"

Andrew paused. "Maybe it is that hard."

I had one of those Andrew moments today, scoffing. This is easy! How about ... HEIGHT FRIGHT? (Acrophobia?) SPRITE MIGHT? Elves are powerful, after all. DWIGHT BLIGHT, that's so apt for "The Office"!

Okay, maybe it is that hard.

Although rhyming themes mostly don't pass editorial muster these days, this one is fantastically tight (no other possible phrases that work). It's also interesting that Daniel and class found four solid phrases all composed of words from a rhyming set. Not an easy task.

The gridwork is unusual for a Monday. Few constructors would leave such big corners wide-open in the upper-left and lower-right — most would break up long entries like IM NOT HERE and TASTE TEST. This makes more sense when you consider Daniel's heavily themeless-based experience. If you can fill big corners, it can lead to more interesting results.

I favor a more traditional layout of black squares, though. Grid flow isn't great in today's NW and SE corners, and dabs of OLIVA, BREE, DAT, ERG, ESS in a Monday puzzle can be off-putting to newer solvers. Redistributing the black squares — fewer in the center, more toward the perimeter — would result in a smoother product.

There is something to be said about a different approach, though, especially when it enables such goodies like MARDI GRAS, TASTE TEST, BUBBLE TEA. And most importantly, it's wonderful to see Daniel take it upon himself to help shepherd along a new generation of crossword makers.