Getting Started with Crosswords

We spend a lot of time talking about crosswords here on PuzzleNation Blog, and rightfully so.

For more than a century now, crosswords have been the standard-bearer for paper-and-pencil puzzles. From your local paper to The New York Times crossword, from online solving to puzzle apps like our very own Penny Dell Crosswords App, crosswords sit comfortably at the apex of the proverbial puzzle mountain, atop worthy also-rans like word searches, cryptograms, and Sudoku.

[Apparently Puzzle Mountain is actually a place. Who knew?]

But in talking about crosswords, it’s easy to forget that not everyone solves them. In fact, plenty of people find them intimidating, given the mix of trivia, wordplay, and tricky cluing that typify many crosswords these days, particularly in outlets like The New York Times, The LA Times, The Guardian, and more.

So today, I thought I’d offer some helpful resources to solvers just getting started with crosswords.

First off, if you need help filling in troublesome letter patterns, Onelook is an excellent resource. Not only can you search for words that fit various patterns, but you can narrow your searches according to cluing, look up definitions and synonyms, and even hunt down phrases and partial phrases.

Along the same lines, there are websites like Crossword Tracker that offer informal cluing help culled from online databases. For something more formal, there’s XWordInfo, an online database of entries and cluing that also serves as an archive of NYT puzzles you can search for a small fee.

The NYT Wordplay Blog chronicles each day’s puzzle, including insights into the theme, key entries, and more, plus they’ve begun amassing helpful articles about crossword solving. Not only are there sample puzzles to download and solve to get you started, but there are lists of opera terms, rivers, and sports names to know to make you a stronger solver.

And if British-style or cryptic crosswords are your puzzle of choice, look no further than The Guardian‘s Crossword Blog, which frequently posts about various cluing tricks employed by crafting cryptic puzzle setters. Their “Cryptic Crosswords for Beginners” series of posts has discussed all sorts of linguistic trickery, covering everything from the NATO alphabet to elementary chemistry.

For other variety puzzles, our friends at Penny Dell Puzzles offer sample puzzles and helpful solving tips for many of the puzzles in their magazines. For example, you can find a sample Kakuro or Cross Sums puzzle on the page for their Dell Collector’s Series Cross Sums puzzle book, as well as a How to Solve PDF.

Is there a particular puzzle that troubles you, or one you find too intimidating to tackle, fellow puzzlers? If so, let us know! We can either point you toward a solving resource or tackle the puzzle ourselves in a future post to provide helpful solving tips!

Thanks for visiting PuzzleNation Blog today! Be sure to sign up for our newsletter to stay up-to-date on everything PuzzleNation!

You can also share your pictures with us on Instagram, friend us on Facebook, check us out on TwitterPinterest, and Tumblr, and explore the always-expanding library of PuzzleNation apps and games on our website!

A crossword like you’ve never seen before

When someone sends me a link, claiming they’ve uncovered the most difficult crossword they’ve ever seen, I’m usually skeptical.

I mean, I’ve seen some diabolical crosswords in my day. From puzzle 5 at the American Crossword Puzzle Tournament and the meta-puzzles lurking in Matt Gaffney‘s Weekly Crossword Contests to the Diagramless and Double Trouble crosswords offered by our friends at Penny Dell Puzzles, it’s hardly tough to find challenging crosswords these days.

But this puzzle, originally created for the 2013 MIT Mystery Puzzle Hunt and made solvable (and rotatable!) online by Greg Grothaus, might just take the cake:

As you can see, there are clues across three sides of the hexagonal grid: the across clues, the down-to-the-left clues, and the up-to-the-left clues.

But these clues are unlike anything I’ve seen before.

It turns out that these are regexps, or regular expressions, sequences of characters and symbols that represent search commands in computer science.

Now, anyone who has used graphing features in Excel or crossword-solving aids on websites like XWordInfo, Crossword Tracker, or OneLook is probably familiar with simple versions of regexp. For instance, if you search C?S?B?, you’ll probably end up with CASABA as the likely top answer.

Of course, the ones in this puzzle are far more complicated, but the overlapping clues in three directions make this something of a logic puzzle as well, since you’ll be able to disregard certain answers because they won’t fit the other clues (as you do in crosswords with the across and down crossings in the grid).

But if, like me, you don’t know much about reading regexp, well then, you’ve got yourself a grid full of Naticks.

If anyone out there is savvy with regexp, let me know how taxing this puzzle is. Because, for me right now, it’s like doing a crossword in a foreign language.

But I’m not the only one who feels this way. When I first checked out the post on Gizmodo, they titled it “Can You Solve This Beautifully Nerdy Crossword Puzzle?” and I laughed out loud when the very first comment simply read “Nope.”

Glad to see I’m not alone here.

Thanks for visiting PuzzleNation Blog today! Be sure to sign up for our newsletter to stay up-to-date on everything PuzzleNation!

You can also share your pictures with us on Instagram, friend us on Facebook, check us out on TwitterPinterest, and Tumblr, and explore the always-expanding library of PuzzleNation apps and games on our website!

Let’s make our own crosswords!

Stumped on what to get the puzzle lover in your household? Well, if didn’t find anything in our Holiday Puzzly Gift Guide, why not make a special crossword just for them?

It’s the perfect do-it-yourself gift, and I’m happy to show you how! Welcome to PuzzleNation Blog’s How to Make a Crossword!

1.) The theme

The most important part of a crossword is choosing a theme. If you’re constructing with ambitions of submitting to the New York Times or the Los Angeles Times, you’ll need something inventive and tricky up your sleeve. 

But if you’re constructing for a friend or loved one, the theme is easy: make it about them!

Come up with your theme entries. For a gift puzzle, these could be hobbies, nicknames, favorite sports teams or TV shows, anything about them, really! Be sure to come up with several pairs of the same number of letters. (It’s a necessity when it comes to crossword symmetry.)

Choosing theme entries is often something done in tandem with choosing a grid, since word placement is a crucial part of building any grid.

For my example puzzle, I’m using a list of celebrity names.

2.) The grid

Constructing a grid from scratch can be tough, so I’d recommend first-time constructors check out sample grids. You can browse the newspapers until you find one that suits your needs, or you can let the Internet do the work for you! has a selection to choose from, for instance. If you’re using a construction program like Crossword Compiler, you can browse options for grids as well.

If you’re looking to start regularly constructing crosswords, I’d suggest building up a library of grids with various theme-entry lengths. (My personal grid library is organized by theme layouts, so if I have two 11-letter entries and two 10-letter entries, I can flip to a 10-10-11-11 in my folder.)

Here’s the grid I’ve chosen for today’s puzzle because it fit the theme entries I wanted. (Ignore the red box. That’s simply Compiler’s cursor.)

Now, I know all that white space to fill can seem intimidating, but placing the theme entries not only helps to guide the fill (the process of completing the grid), but breaks up that white space into manageable sections.

Here is the same grid with the theme entries placed:

3.) The fill

Filling a grid by hand is time-consuming but worthwhile, because you can be creative with using pop culture references, proper nouns, phrases, abbreviations, and whatever else the grid demands.

Since I was using a demo version of Compiler, I opted to try out its Autofill feature to see what my options were. As you can see, I ended up swapping the locations of SILVERSTONE and CHAMBERLAIN to improve my chances of a successful fill.

After settling on the fill for the center section (spreading from bottom left to top right), I started working on the fill for the top left portion.

Here’s the best fill the program could offer:

But I wasn’t satisfied with it, so I began tinkering on my own.

That’s probably the most daunting part of making your own crossword, but there are numerous resources available to the aspiring puzzle creator.

Not only are there Autofill programs like the one employed by Compiler, but there are also websites where you can input letter patterns and see what your options are. Both and are terrific resources.

Here’s the result of my own tinkering:

There would be further gridwork throughout the editing process, as I eliminated abbreviations, vocabulary I gauged as too difficult, and grievous examples of crosswordese.

Don’t get discouraged! I had to try lots of different word combinations to make it come together. All of which was time well spent in my opinion.

Here’s my completed grid:

As you can see, including phrases and pop culture references definitely helped out, especially at middle left where JAWAS was a handy inclusion, as well as bottom center where IFI and AFOOL are crossing.

Which brings us to the grand finale.

4.) The cluing

Now, cluing takes on an entirely different dimension if you’re hoping to publish your crossword, versus the cluing style you’d use for a homemade puzzle for a friend or loved one. When it comes to published puzzles, your clues need to be interesting, engaging, and more than a little crafty.

(Note: It’s true that the theme is often what sells your puzzle to editors like Will Shortz, but a reputation for clever cluing is always a good bonus.) 

For instance, a puzzle of celebrity names could prove a bit boring when it comes to cluing, but I chose the entries I did intentionally, because I already knew the clues I wanted to write for them. (These clues were based on a series of outstanding puns a friend of mine made on Twitter.)

My theme is Celebrity Groupings, and the clues reflect that.

17 Across: A ____ of tuxedo belts
8 Down: A ____ of discarded Old English words
53 Across: A ____ of shriveled utensils

In this instance, the clues make all the difference.

Of course, if you’re making a crossword as a gift, the above still applies. Cluing makes all the difference. You can tailor the clues specifically to the intended recipient. Inside jokes and references should run rampant, even for the words used in the fill.

For 37 Across, you could say “What Uncle Rob does for at least three days longer than necessary.”
For 39 Down, you could clue it as “General Kittybuns’s sign of pleasure.”

Have fun with it! If you can make them laugh or say “Oh yeah!” and remember a fun moment while they’re solving, it makes the gift even more special.

And if you do try constructing your own, let us know how you did! We’d love to see what our fellow puzzlers and PuzzleNationers come up with!

[Stay tuned, aspiring constructors! On Thursday, I’ll be posting part 2 of today’s How To, featuring advice from published constructors and puzzlemakers!]

Thanks for visiting the PuzzleNation blog today! You can like us on Facebook, follow us on Twitter, cruise our boards on Pinterest, check out our Classic Word Search iBook (recently featured by Apple in the Made for iBooks category!), play our games at, or contact us here at the blog!