
I’ve been a crossword junkie since I was a kid. I come by it honestly, though. My mom has always been into puzzles. Most girls get into their mother’s make-up; I got into her monthly World of Puzzles magazine.
I started my crossword journey with the weekday puzzles and those $3 booklets from the supermarket magazine aisle. It did not take long to dominate those puzzles, and now those Easy & Fun crosswords are an insult to my mad word skills.
With more puzzles under their belt, crossword aficionados quickly learn that clues follow strict rules and often reappear in puzzles (a.k.a crosswordese). Frequent puzzle solvers are well aware that “eft” is a 3-letter term for salamander, a “nene” is a Hawaiian goose (and state bird), and an “amah” is an Asian nanny.
We expect the answer to mirror the clue. For example, if the clue is is plural, then the answer is plural. If the clue is abbreviated, some or all of the answer is abbreviated. If it’s an adverb or superlative, then so is the answer, and so on…
When I attempted the New York Times Sunday Puzzle in my younger years, I would get owned. I’d be lucky to fill in a corner. The answers I thought were correct were not. People I know who do crosswords regularly get stumped at the Sunday Puzzle. It is a truly humbling experience to come before editor Will Shortz’s epic word grids, even as a veteran solver.
Some puzzle enthusiasts hit a wall and content themselves with easier puzzles. They wonder how they deftly complete the “hard” crossword in the airline magazine, but cannot fill in more than a few squares of the Sunday Puzzle. Why? Because the Sunday Puzzle takes all the rules you know about solving crosswords and says F*** YOU!
Tried and true crossword tips, along with a full head of trivia and decent vocabulary, only get you so far. Below I unpack 3 riddles to help you on your way. The Sphinx himself offers similar insight into tackling these puzzles.
To fill in the box, think outside of the box.
I have seen puzzles where letters are replaced with symbols (e.g. the symbol for pi, the letter X for “cross”), and others where the answer is not simply across or down. Often, the puzzle theme provides some clue of what to expect, and you may have to fill in a clue somewhere in the puzzle to get a better sense (e.g. the clue states something like “Like the answers in this puzzle” and the answer is “climbing” means that you may need to look in a different direction for the answer).
If you find part of your answers seems right, but not quite fitting the boxes, you could be dealing with a puzzle of this type. In my opinion, these are the most difficult puzzles.
Be hesitant with your pen, but daring with your thoughts.

Attempting this puzzle in straight pen is like having unprotected sex on a one-night stand. You might get lucky and the answer is correct, but you’ll likely end up with a hot mess. A scratchy, scribbled mess…
You can get the app, but I am old school and prefer solving in print so don’t fry my eyes with screen-glare when cross-referencing.
As someone who believes pencils are for drawing, I get you, fellow pen-lover. I actually use a ballpoint pen and write very lightly what I think the answer is. I also check it with the perpendicular clue to make sure the answers line up.
However, to solve this puzzle, you have to put down a clue and see what happens, even when unsure of the answer. Write something and see what happens. For short answers, visually imagine the letters on the grid before writing it down to see if it lines up with the respective across or down answers. If you are shut down, you have not put down any wrong letters.
A clue has many meanings, but only one answer.
A crossword clue ending in a question implies the answer is a play on words. The harder the puzzle, the more these clues appear. But for the Sunday Puzzle, don’t assume a non-question clue is straightforward. Any clue can have an indirect answer. Exceptions are Proper Names / Fill-in-the-Blanks (i.e. straight facts you either know or don’t).. For any level of crossword, I recommend beginning the puzzles with these.
For the Sunday Puzzle, you can’t get too cocky. You could get a clue “Capital of Massachusetts.” Obviously, the answer is Boston, but it could be an alternate name for the city, like “Beantown.” So when the answer is 8 letters rather than 6, get over that WTF moment and think of what else that answer is called. The clue will not always indicate whether the answer is straightforward, a slang term, etc.
Sometimes the “know-it-or-you-don’t” clues are outside your knowledge base. Even seasoned cruciverbalists encounter this. A 4-letter word for excrement happens…
I suppose one positive side of aging is knowing more. As a younger solver, I felt many clues were before my time. However, I have seen crosswords with very current references and “text-speak” clues younger generations would know. I envision “bae” or “boo” joining the crosswordese ranks for clues such as “dear one” or “main squeeze”.
Also, since 8+ letter answers appear more frequently in this puzzle, don’t assume the solution is only one word. Particularly for plural clues.The probability a plural clue will end in an “S” is still more than 50%, but less of a guarantee.
Enter if you dare…
Solving the Sunday Puzzle is a rewarding experience. It is a great way to pass the time while stretching your mind. Especially over a cup of coffee.
A word of caution: once you start solving these regularly, you will find the easier puzzles offer the mental stimulation of watching paint peel. I recommend crossword booklets that contain many Sunday Puzzles. For the cost of a movie ticket, I get 50+ hours of mind-bliss.
Happy solving!