How to Enjoy Crossword Puzzles

In my every day normal routine in Las Vegas there are two events to which I look forward each day. The first is dinner at Chipotle. I still eat there virtually every day when it’s an option, and still delight in it every time. The second is when I get the notification at the top of my phone that tomorrow’s crossword is available.

For over a year I have done the NY Times crossword puzzle just about every single day. I may have missed one or two, but I went back and completed all of them. In fact, I’ve done somewhere around 2800 puzzles as I write this.

When I first started I could barely get through a Wednesday. Often I’d have to check the puzzle or reveal letters. Now I’m currently on a 250+ day streak and I believe that I’m at the level where it would be pretty surprising if I couldn’t fight my way through a puzzle. They’re still sometimes very hard (1 hour+ for saturdays on rare occasion but I can usually figure it out.

I very rarely recommend “fun” things on this blog, but I’m wholeheartedly recommending crossword puzzles.

Crossword puzzles are the perfect balance between fun and progress. They’re really engaging and fun in the same way that figuring out how to build something is fun. Not delightful, but satisfying. At the same time, you’re building a skill.

To be fair, I’m not sure exactly what that skill is. I feel like I think differently about words now than I used to. Crosswords force you to think about the different ways we use words, and all the things each one can mean. There’s also a lot of strategy. You don’t just run through and answer every question you can. That works for Mondays, but by the time you get to Saturday you need a lot more than that.

Of all leisure activities I do, crosswords seem most worthwhile, except for maybe good conversations with friends.

To start, download the NY Times app for your phone. You can also do it online. There’s usually a promotion for a free month or week.

Start with the Monday crosswords. Do the most recent one, and work backwards in time, doing all other Mondays. Mondays are easiest, Saturdays are hardest, Sundays are medium level difficulty but are huge. Thursdays are always “themed” puzzles so figuring out the theme can be a challenge.

Begin a puzzle by just browsing through and finding an answer that you know. On a Saturday I may not know one absolutely until halfway or more of the way through the clues. Many of the clues cannot possibly be solved without any letters revealed.

Once you find an answer, start working on the clues that intersect with that answer. Having even one letter revealed is a major advantage because it can rule out a lot of possible answers.

In general, try to solve the words that already have the most letters revealed. This limits your search space and also helps you check the words you’ve already put in.

When you get stuck… keep at it. On a hard puzzle I’ll sometimes be totally stuck for 10 minutes. Then go do something else for a while. When you come back you’ll have a different state of mind and some answers might be obvious.

If you get stuck, use “check puzzle” or “reveal square”. Try not to, but don’t feel bad about it. There are a lot of unwritten crossword rules that you only learn by seeing puzzles solved, so you’ll need to use them at first.

Once you can reliably solve Mondays with few or no cheats, move on to Tuesdays. Repeat for Wednesday.

Things get much more difficult going from Wednesday to Thursday. So even if you’re breezing through Wednesdays, you’ll probably have to cheat a lot when you start Thursdays.

I think of Monday-Wednesday as one group, Thursday-Saturday as another, and Sundays as their own. It’s always a big adjustment getting used to another group.

Once you can consistently do Saturdays with just a few hints, cut yourself off cold turkey and refuse to ever use hints. I relied on hints for too long, until I finally realized that the puzzles are so hard that sometimes you just have to sit with it, and that by using hints I would never build that skill. Now I never use them.

I skipped Sundays until I become really proficient at Saturdays, because then I wanted to start building a streak. Sundays seem to be about Thursday-Friday difficulty to me.

I generally hate paying for monthly subscriptions that aren’t necessary, but I love paying for the NY Times Crossword subscription. For me it’s the best possible entertainment value, and I can’t help but feel that it’s doing good things for my brain at the same time.


Photo is my friend Megumi whisking matcha at Higashi-ya in Tokyo. I couldn’t find any photo remotely crossword related.

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