Crossword puzzles, like Jeopardy! or pub trivia, are a quintessentially knowledge-nerdy fascination. They combine both high-brow and low-brow knowledge, ranging in diverse fields from sports, music, and movies to ancient history and books of the Bible. Throw in tricky clues laced with puns and an interlacing grid where one answer can unlock a whole section that was nebulous just moments before, and it is no wonder why some of us geek out on them.

I haven’t always been into crosswords, though. I’ve enjoyed doing the occasional one in the back of an airline magazine when I ran out of things to read, but I’ve never been someone who goes straight for the page in the newspaper…or really been someone who has had paper newspapers as an adult. But about three and a half years ago, I downloaded the New York Times Crossword app and signed up for a subscription.

The New York Times Crossword has been around since 1942 and is consider the gold standard in crosswording. It runs one puzzle a day, starting with the easiest on Monday and increasing in difficulty until Saturday. (The Sunday puzzle is about a Wednesday or Thursday difficulty, but is a larger 21×21 grid instead of the usual 15×15.) Originally when I started, I could barely finish a Monday without needing to check my answers, but as I solved more, I began to get a little better. Still, having a one week streak seemed far, far away. But with a lot of practice, and over 1,000 puzzles solved, I recently hit 365 consecutive solving days.

As I write this, I’ve kept that streak going into the 400s. I am far from a great solver, but I’ve learned a lot, and so I thought I would take this post to list out some things that have helped me along the way.

Start with Mondays and do a lot

Since Mondays are the easiest, you’ll get a lot more experience, and have more success, if you start by just doing lots of Monday puzzles. If using the app, you have access to the archive of past puzzles, so you can go back and solve Monday puzzles from each week back to November 1993, meaning there are more than 1000.

Use lots of passes

Start by going through all the across and down clues, looking for the easy ‘gimme’ ones that have only one correct answer, such as ‘fill-in-the-blanks’. Then take a second pass and see how the downs might now help you get more acrosses, etc.

Once you feel stuck, walk away. It is magic how you can have no idea what any of the remaining clues are, but if you walk away for an hour or so, when you come back there will be one or two that pop out that now help you knock over more dominos. Plus, your leg might be asleep from sitting on the toilet too long (just me?).

Learn ‘Crosswordese’

Part of being good at crossword puzzles is knowing bits of trivia and language, and part of it is knowing what crosswords like to do.

Know your common answers: Three letter musician? It’s either Brian ENO or Yoko ONO. Three letter fish? Sometimes AHI tuna, but almost always it is EEL. Other answers like OREO, ETSY, etc. probably come up once every other week.

Know your tenses, etc.: If the clue is plural, the answer is plural. If it is past tense, the answer is past tense. And if the clue has a foreign word or country name, then the answer will be a foreign word from that language.

Embrace the pun: Crossword puzzles love puns, especially if the clue ends in a question mark.

Don’t be afraid to ‘cheat’

Trying and getting frustrated, but never finishing, is a great way to give up crosswords. And while there is equally no fun in just looking up all the answers and copying them down, there is a gradient of ‘help’ in the middle that can give you just the push you need. Some options:

• Ask a friend
• Use the NYTimes accompanying hint article under the ‘i’ menu if using the app. (Also, a fun nerdy way to learn more about the people who made the grids themselves.)
• Looking up a word you don’t know in the dictionary

If you are a ‘purist’ who shuns anyone who uses anything other than a pen and piece of newspaper, I leave you this quote:

Let me say something that may be controversial, but it needs to be said: It’s O.K. to look something up when solving a crossword. Crosswords are ultimately learning tools, whether you’re learning some trivia or an interesting new word or phrase. When you look something up, you’re learning so you’ll know it for next time. Of course, some solvers may tell you that looking up the answer to a clue is “cheating,” but to us, that way lies frustration and a path to giving up. And that’s no fun. Crosswords are a game, and games are supposed to be fun. Still not sure looking things up is fair? Here is outright permission: “It’s your puzzle. Solve it any way you like.”

Will Weng, the second crosswords editor of The New York Times (1969 – 1977)

Conclusion

I view this a little like running. Sure, there are people who run races to see if they can be better than all of the other people. But for me, I’ll do a race and just try to do better than I did before. Or I’ll do something way out of my league of difficulty, like a Half Ironman on a single-speed bike, and just see if I can finish.

But most of the times these days, I just do it for the fun of it. For the quiet chuckle when I get a clever clue. Or for the tiny fist pump when I’ve correctly solved the grid. Then I’ll get up, flush, and wash my hands.

Additional Resources

Here are some additional resources that go into more detail on some of the Crosswordese techniques:

• The plan to solve at Saturday puzzle in 31 days from Max Deutsch, whose month-long challenge to improve his self-portrait skills inspired my own similar challenge a few years ago
• The crossword guide from the New York Times (although the page formatting is weird for me)

Bonus: A Wired Magazine piece with David Kwong on how to create a crossword puzzle where the video itself has secret clues for you to find