I started doing crossword puzzles sometime in 2019. After learning the basics of American crossword puzzles, the best way to improve is to solve daily.

As a budding cruciverbalist you develop a few key skills. The NYTimes website has an excellent guide on the basics of solving. Beyond the basics (which I’m just barely beyond), there are a few other pieces of information you’ll learn along the way.

The New York Times digital crossword subscription is currently $19.97/yr. If you’re a print subscriber (I subscribe for Sundays only) they throw in a digital subscription with crossword puzzle access for free. Prior to subscribing for the Sunday print edition I used to use my local library’s digital access for free from home—which was nice for not only crosswords but also the paywalled NYTimes Cooking section.

In 2015 I bought a Brother HL-L2340DW black and white laser printer for $100 and I highly recommend it to everyone. I use it to print the crossword and work on it over dinner with my partner which I find more relaxing than staring at my computer or phone.

Although I do the print version of the crossword, the NYTimes website has a number of nice features if you solve using their interface. You can track your solve times daily along with rudimentary descriptive statistics about your solve. There is also a leaderboard so that you can share your solve times with your friends and coworkers.

If you prefer offline digital solving there are .puz files available from the NYTimes that you can use along with a locally installed crossword application. The NYTimes recommends “Across Lite”, which I’ve never used. I’ve played with “cursewords” which is an ncurses interface for .puz files that is pretty usable depending on your terminal environment.

The New York Times crossword puzzle ramps up in difficulty throughout the week. Monday is the easiest puzzle to solve. Saturday is the most difficult. Sunday is roughly mid-week difficulty but bigger (Sunday is 21x21 with 140 words max vs 15x15 with 72–78 word max for other days – 72 words if the puzzle has no theme).

When you’re just getting started it’s best to start with the Monday puzzle and see where you get stuck. For the new solver I’d wager you’ll slow down by Thursday. If you keep pushing through week-after-week, you’ll get faster and your solve percentage will improve.

As a result of my proclivity for print I only have 14 solves in the NYTimes interface currently. My average Friday solve time is 55:13 and I don’t have any Saturday solves. I’m hoping this is not indicative of my current abilities, but it’s probably not too far off. I have slowly solved many a Saturday puzzle. Not every Saturday puzzle though.

The Monday through Thursday puzzles tend to have themes. Most of them punny. Many of the clues are question mark clues indicating a high-likelihood of being groan inducing. Cracking the puzzle requires a keenly developed sense of the type of jokes that appeal to people who do crosswords for fun. When you first start solving, the clue, “They often come out at night?” does not evince the answer, “FALSETEETH”. Bravery in the face of bad puns is a distinguishing characteristic of a crossword puzzle solver. The Friday and Saturday puzzles (and sometimes Thursday puzzles) tend not to have themes and focus on difficulty. I personally find themeless puzzles less fun than themers – the groan-factor of cracking a themer becomes an addiction.

What it means to solve a puzzle is pretty flexible. Is it OK to lookup the spelling of SCHWARZENEGGER? What if two proper names cross each other – did you solve the puzzle if you had to look one up (names in crosswords are controversial – they have the same problems as Wikipedia’s Notability Criteria – including all the issues of diversity, equity, and inclusion).

Only you can say whether or not you solved a puzzle. And (even though puzzles are getting easier than ever) I still cheat even by my own standards. There are useful websites for cheating: onelook.com and xwordinfo.com for example. I also use the Linux dictionary with grep to cheat on occasion – for example say I had the clue “kind of sauce” and I had _AR_A_, I could use grep -iP '^.ar.a.$' /usr/share/dict/words to find TARTAR.

The key skill that makes you look smart to the uninitiated really comes down to a familiarity with common crosswordese. Crosswordese describes words that appear more frequently in crosswords than they do in real life. As a player of the crossword you know that MOUNT ETNA is the Sicilian eruption in the Aeneid by Virgil; that ESAU is one of the twin sons of Isaac; and that Brian ENO (who I think as a generative ambient musician) is the glam rocker from Roxy Music. Lots of vowels and unique vowel/letter arrangement make a good candidate for crosswordese. I’ve recently noticed that Gal GADOT is a rising star in the world of crosswordese, seemingly outpacing many other contemporary superheroes.

Once I’ve “solved” a puzzle (for my self-defined and highly flexible value of “solved”), I immediately go to Rex Parker Does the NYTimes Crossword Puzzle. I do this for many reasons:

1. To learn more about the puzzle and its constructors
2. To see if there are any theme elements I hadn’t considered – Rex does a great job of deep-diving on themes
3. Often I go there to find out if anyone was mad about the clue I was mad about
4. Just as often I’m there to be flabbergasted that Rex hated a puzzle I loved

All this is to say that while I often completely disagree with Rex Parker and Rex Parker’s comment section it remains my little crossword community and by lurking there I get an extra dimension of enjoyment out of the puzzle thanks to his blog.

Finally, while the NYTimes crossword is the marquee crossword, there are many smaller crossword sites on the internet that are worth your time:

• The American Values Club crossword – focuses on inclusion and feels more geared towards my small sliver of the world’s Overton window
• The Inkubator – crossword puzzles by women
• Glutton for Pun (Erik Agard’s site) – a really fabulous constructor whose clues are often sooo groan-inducing that it’s magic