On solving crosswords

One of my major hobbies is crosswords, and if you’re around me for a while you’ll hear me talk about them sooner or later.

I started doing crosswords in the New York Times on a regular basis probably back around 2013 or 2014, and now also subscribe to several other publishers. They are a fun new thing to look forward to every day. A well-constructed grid, a clever clue, or an inventive theme (many puzzles have a theme that threads its way through the clues) is a real pleasure to figure out.

The most rewarding thing has been to watch myself gradually improve. The NYT’s puzzles ascend in difficulty from Monday to Saturday, with the Sunday being a large puzzle at about a Thursday difficulty. At first I struggled to get through anything harder than the early-week puzzles. But gradually, and with some patience, I began to crack the occasional later-week puzzle, then started to do it more regularly, and finally got to the point where it was unusual to be unable to solve one. Similarly, the first time I saw a rebus puzzle I thought, “How could anyone ever solve this?” But again, after putting several of these under my belt, I found myself able to identify and conquer these too.

All the while, my times fell. When I started solving puzzles in under 10 minutes, the idea of getting to 7 minutes seemed impossible; where would that saved time come from? But I got to 7 and wondered how I could ever get to 5, then 4:30, etc. These days I usually clear the Monday puzzles in under 3, and I’m still hoping to solve one in under 2 someday! (My best is 2:05.) Each target that once seemed unreachable eventually fell.

This isn’t to brag (OK fine maybe just a little), but to encourage you to try them yourself. Regardless of natural talent, everyone can and does get better simply by doing lots of puzzles. There are patterns you recognize, words you see repeatedly, trivia you learn, and ways of “laterally thinking” about the phrasing of clues that you develop and strengthen like a muscle. No matter how fast you are overall, I think everyone can enjoy the rewarding experience of finally solving a puzzle for the first time and seeing the whole grid there on the page, then nailing a few harder ones, and watching those times drop.

Crosswords are also much less trivia than people realize, and much more about the ability to work with the shape and syntax of words. The way I’d put it is that someone who is good at Scrabble and terrible at Trivial Pursuit will be a better solver than someone who is the other way around. (Though being able to do either well would help.)

If you do find yourself sliding headlong into the world of crosswords, you can attend one of the tournaments. There’s typically no elimination except for the very final round; it’s more participatory, like a road race, where everyone does the same puzzles and you can see how you stack up against the strongest solvers out there. The American Crossword Puzzle Tournament (ACPT) is the big one and has been running for decades, normally in Stamford, CT in the spring. A few others I’ve attended are Lollapuzzoola (summer, NYC), the Indie 500 (spring, DC), and Boswords (summer, Boston).

Tournaments normally happen in person and on paper, with an at-home option where you can score yourself unofficially. But during COVID, some of them have switched to online formats with success. Lollapuzzoola and Boswords recently conducted their 2020 iterations online, and I thought they were both great fun; the technology worked well, there was good banter in the chats, and most importantly, many more people were able to participate than ever before. The crossword world is heavily Northeast-biased, and I feel for people who would love to participate but who can’t spend the time and money to fly out here. Even after this pandemic clears up, fingers crossed, I have a hunch that there will be a permanent shift towards online formats, perhaps with new online tournaments popping up alongside the old in-person ones.