How to Get Started Solving The New York Times Crossword Puzzle (Published 2017) (2024)

This is probably a beginning solver’s most common mistake.

You know what it’s like: You have some downtime on a Saturday and you look around for something to pass the time. Your officemate keeps bragging about his ability to finish The New York Times Crossword. You hate your officemate.

So, not to be outdone, you pick up the paper or download our app and turn to the Saturday puzzle. How hard could it be?

Fun Fact: The Saturday crossword is actually the hardest puzzle of the week. Contrary to popular belief, the Sunday puzzles are midweek difficulty, not the hardest. Mondays have the most straightforward clues and Saturday clues are the most vague or involve the most wordplay. Some later-week puzzle clues may require specialized knowledge.

Just to drive the point home, let’s take a look at the difference between a Monday clue and a late-week clue for a popular crossword entry. OREO cookies (answers in puzzles are generally written in all capital letters) are such a popular entry in crosswords that they have been dubbed by some as the “official” cookie of the crossword. A typical Monday clue for OREO will be very straightforward and drive you almost directly to the answer.

“Nabisco cookie”
“Cookie with creme filling”
“‘Twist, Lick, Dunk’ cookie”

And here are some late-week clues, which might require more specialized knowledge about these delicious treats:

“Snack since 1912”
“It has 12 flowers on each side”
“Sandwich often given a twist”

We weren’t kidding you. There is a big difference between a Monday puzzle and a Saturday puzzle.

That doesn’t mean that you can’t work your way toward solving a late-week puzzle – and we recommend that you do, because they’re fun – but it takes experience and patience.

If you’re just getting started, though, make your life easy and solve as many Monday puzzles as you can. Eventually, you’ll be ready for more of a challenge, and that’s when you move on to Tuesday puzzles.

Once you’ve learned an answer and how it’s clued, you can almost be sure you’ll see it again. The brain works in weird and wonderful ways, and when you start solving crosswords consistently, you’ll surprise yourself when you say, “Hey, I know that one!”

Let’s look at our friend the OREO cookie again. The entry OREO has appeared in The New York Times Crossword a total of 389 times since the puzzle began running in 1942. Of those, OREO has been clued in one form or another as the cookie a total of 278 times.

Fun fact: Before 1993, when the editor Will Shortz took over, OREO had been clued almost exclusively as the combining form or prefix of the word “Mountain.” Thanks, Will!

“Keep working the puzzle every day as best you can. For a solid month after I started regularly attempting The Times puzzle, I couldn’t even solve Tuesdays. But I gave it a shot every day anyway, and I’m willing to bet that the exposure helped me improve faster.” – Tyler Hinman, five-time winner of the American Crossword Puzzle Tournament, featured in 2006 documentary “Wordplay”

“Do more puzzles. Really, that’s the only advice I have. The more you solve, the better you’ll get. It’s also useful to read Wordplay and/or other puzzle blogs, which helped me internalize the tricks and tropes of crossword clues while I was learning the ropes.” – Dan Feyer, seven-time champion of the American Crossword Puzzle Tournament

Puzzle hack: Solving puzzles consistently helps builds up your skills, because many crossword answers appear repeatedly.

Source: XWordInfo.com

You already know more than you think you do. Scan the clue list for the things you already know, or “gimmes,” and write those in first.

To borrow a sports term, a puzzle or individual clue on topics that you know well is said to be “in your wheelhouse.” You’ll be able to find at least a few things in each puzzle that you know.

“Good crosswords connect to everything in life.” – Will Shortz

You can also pick out the clues that are meant to be easiest and tackle them first. Fill-in-the-blank clues, such as “___ of Arc,” for the answer JOAN, tend to be easier because your brain just loves filling in missing information.

Don’t believe us? Try these clues that are designed to be easy for most people:

1. “Leonardo daVinci’s ___ Lisa”

Even if art isn’t your thing, your brain knows the answer to this: It’s MONA, for MONA Lisa.

These easy clues don’t even have to be fill-in-the-blanks. Your brain will do it even when there is no blank.

2. “Hockey disk”

Not into sports? Not to worry. Surely you still know what a hockey PUCK is.

You can confirm whether your answer is right by solving the entries that cross it.

Let’s look at an example of why it pays to work those crossings. You might not see this in a Monday puzzle, but say the clue is “Black Halloween animal,” and you have confidently written in “CAT.”

Then you look at the entry that crosses the first letter of CAT and the clue is “Honest ___ (presidential moniker).” The answer to that one is ABE, so CAT must be wrong.

Now what do you do?

“When you enter an answer, immediately check the crossing entries through it. Start with the least common letter and go from there: If you’ve written in the word JUICE, look at the clue that crosses the newly entered ‘J.’” – Joel fa*gliano, Mini Crossword writer and Digital Crosswords editor

The trick is to stay flexible and remember that a BAT is also a “black Halloween animal.” Tricky, but doable.

“The key to solving crosswords is mental flexibility. If one answer doesn’t seem to be working out, try something else.” –Will Shortz

Conversely, you can also work your way through an answer that you can’t get completely by solving the crossings. Once you have enough letters filled in, take your best guess based on the pattern of letters you’ve uncovered.

It’s much easier to solve a clue where the answer already has some letters filled in than to try to solve one that’s completely blank, so once you have that all-important foothold, go back to those areas and try to expand your solved territory.

Solving shorter words is helpful, too: A three-letter answer with a single letter filled in may be easier to solve than a longer answer with one letter filled in.

Some solvers will tell you that looking up the answer to a clue is “cheating,” but it’s not. When you look something up, you are learning so you’ll know it for next time.

Whether it’s trivia or an interesting new word or phrase, crosswords are ultimately teaching tools.

And, quoting the former New York Times crossword editor Will Weng, one of his predecessors, Will Shortz reminds us that “It’s your puzzle. Solve it any way you like.”

“Feel free to look up answers you don’t know and read about them – you’ll likely see those answers and clues again.” – Howard Barkin, 2016 winner of the American Crossword Puzzle Tournament

We’re big fans of the brain here, especially its incredible work ethic. But even brains get tired, so if you are stuck at some point in the puzzle, one of the best things you can do is put it down and take a break from it for a while.

We’re not sure how this works, but your brain will continue working on the clue in the background while you go about your day. When you come back to it, you might be surprised at the “Aha!” moment you experience when you thought you didn’t know the answer.

Your wheelhouse might be stuffed with sports trivia. Your BFF’s wheelhouse might be crammed to the rafters with a deep knowledge of opera. Vive la différence, right?

Solving with another person can work to your advantage. You know stuff your friend doesn’t know, and he or she knows stuff that you don’t know. That’s roughly twice as much stuff that you can solve, and it’s a good excuse to spend time together.

In fact, you never know when it could lead to something more.

“When we started dating, my wife and I would meet up on Sunday mornings to do The New York Times Crossword together. I was terrible at it, but solving with a friend quickly made me a better solver.” – Jeff Chen, New York Times Crossword constructor and assistant to the regional manager of XWordInfo.com.

Some clues end in question marks, and those question marks indicate that a clue is not to be taken literally. The answer might be some sort of pun, or you might have to think of alternate ways in which the words in the clue might be used.

For example, you might see a clue like “Job that might involve watching the kids?” The answer has to be BABY SITTER, right? But what if we told you that the answer is only eight letters long?

Here’s how to crack this clue: Think about what other kinds of “kids” you know. Aren’t baby goats called kids?

So a “job that might involve watching the kids” that has eight letters would be a GOAT HERD.

Trust us, you’ll learn to love this part of it. Playing with words is addictive.

Solving a New York Times crossword is not easy, but it should be satisfying. Even if you only get a few answers the first few times, keep on solving. It just gets easier – and better – from there.

But don’t limit yourself. Try to master the skills you need to get started, and then push yourself to go further into the week. That’s where all of that devious, delicious wordplay is tucked into the clues, and where the fun in solving crosswords lies.

And your officemate will eat his liver out.

Puzzle hack: Don’t forget to pat yourself on the back when you pick up a new solving skill.

Want to give your new skills a workout? We made some easy Mini crosswords for you. Try them now for free.