How to make a crossword

Here’s a demanding but rewarding geeky gift idea you can steal: make a personalized crossword for a friend.

This isn’t for the faint of heart. It’s taken up a lot of my free time for the last week. But if you know someone very well, a few dozen crossword hints can stew together years of shared experience. And when you’ve finally laid out the finished product, it’s a sight to see: your hand-drawn black-on-white grid really pops off the page. Making a crossword gives you a sense of both intimacy and ritual, not unlike the joy of making a fancy meal for company.

Here are the lessons I learned.

First, decide how big your crossword will be. The gold-standard New York Times daily crossword is 15 boxes by 15; the Sunday version is 21×21. I went for 15 on a side, though that was coincidence.

Next, since this is a personalized crossword, sit down with a notebook and write out a bunch of words, names and phrases related to things both you and the recipient know about. It’s great fun, and you’ll need a lot of ideas, so do this for a while. But beware: not all your brilliant ideas are going to survive this journey with you. In the end, filling my puzzle took 77 phrases, many fairly impersonal and about two-thirds of them composed on the fly.

If you want, include some themed elements — between two and six long phrases that are somehow related to each other. Mine: BARTLET4AMERICA and YOUR2CENTSWORTH. You shouldn’t expect the recipient to fill these in right off the bat; they’re more of a reward for completing the first 80 percent or so of the puzzle. Make sure your grid will fit them.

Now it’s time to start filling in your dummy grid — on scratch paper, of course, and with a pencil. (Dear god, will you need a pencil.) Be bold! You’ve got a blank slate. Just play a little Scrabble for now, crisscrossing a few of the words on your list. You’ll be creating problems, but there’s simply no anticipating them now. Here’s a point that’s harder to remember than you might think: every phrase must be preceded and followed by either the edge of the puzzle or a dark cell.

As you do this, keep in mind a few rules of proper crosswords, most of which I circumvented once or twice:

  • The four corners of the crossword should all be lettered squares. No reason for this, but it seems to be the professional tradition.
  • Every lettered square should be part of exactly two phrases: one down, and one across. This is necessary so that completing the puzzle won’t depend on any single hint; there should always be two ways into a box. This means you can’t slip a phrase between two darkened cells, or between a dark cell and the grid’s edge. If you must leave a lettered square on its own, make sure the hint will be a fairly easy one.
  • Avoid two-letter words. They’re no fun to guess.
  • Avoid big blocks of text. Anything bigger than 4×4 is going to be a bitch to assemble. So try to slice up the puzzle with nice diagonal hedgerows of dark cells.

Today’s happy crosswordsmith has a free online tool that his forebears would have killed somebody for: WordNavigator. It’s mostly designed to help people finish crosswords, but it does the reverse job just as well. It searches a dictionary for words to your specification, with ? for a single wildcard character and * for an unlimited number of them. For example, searching for j??l turns up “jail,” “jell” and “jowl”; *yt would give me all five words that end in “yt.”

Unfortunately, WordNavigator’s database doesn’t include acronyms, proper names or multi-word phrases, and you won’t be able to do this without acronyms, proper names or multi-word phrases. That’s where AcronymFinder comes in. Most acronyms it’s collected are crap, but the best are atop each search. And it won’t accept wildcard characters, unfortunately.

If, as you compose hints, you’re looking for people who share a particular name, Wikipedia can help. Here’s the disambiguation page for “Glass.”

According to Sam Bellotto Jr., who has lots of good advice as to how to make a crossword for a general audience, about a third of your hints should be straightforward, a third should be somehow clever and the rest should be a mix of fill-in-the-blanks, famous-name completions and only-in-a-crossword words such as BAHT or ITEA. For a gift crossword, I’d go heavy on the pop culture and light on the ITEA.

Finally, there are all the hint conventions that crossword people are accustomed to:

  • Preserve the part of speech and plural status.
  • If the answer’s an abbreviation, use an abbreviation in your hint.
  • If the answer’s in a foreign language (shudder), hint using the language or a geographical cue.

And so on.

Okay, so you’ve penciled the last wonderful letter onto your scratch paper. Time to make the physical product. Choose a high-quality sheet of paper, something that’ll soak up the ink well, and mark off your grid with a ruler, making the boxes not much smaller than a centimeter on each side. Carefully … carefully … blacken the appropriate cells. Then, in the upper left-hand corner of every cell that will begins a word, enter a number. Progress as you would in a book, from left to right and top to bottom: your two lists of hints (“across” and “down,” always in that order) will skip numbers, but that’s okay as long as they fall in sequence. What you don’t want is any number to appear in more than one block.

Congratulations. You’ve created a great-looking and completely unique work of art. If it’s used right, it won’t last longer than a good Thanksgiving dinner, but that’s what’ll make it magical.


11 Responses to How to make a crossword

  1. Dana says:

    OMG. I cannot imagine making a crossword puzzle by hand. You are some sort of handmade geeky gift god.

    I used to use Puzzlemaker to make vocabulary crosswords for my ESL class, and it doesn’t even come close to that amount of attention to detail. It often gives you very abstract designs of ocassionally intersecting lines, which clearly violates the “every box should have two ways into it” rule. Then again, all their clues were definitions of words they were specifically supposed to have just learned, so I don’t feel so bad.

  2. B Barron says:

    Mike, this is SO INTERESTING! Now that I’ve read your blog, I would like to drop everything I’m doing right now, lock myself in a room with my laptop and Blackberry (for internet connection), parchment and appropriate tools (pencil, eraser, ruler), and a large bag of gummy bears, and not come out until I had completed one of these for my sister, my daughter, my best friends….

    The down side of such impetuous behavior would be that I’d lose my job, most of my teeth (from the gummy bears) and maybe my mind. But it could be worth it!

  3. Mark says:


    The teeth and your mind are both legitimate to worry about, but don’t you more or less work for yourself? Besides, gummy bears, in and of themselves, are almost always worth it.


    You rock my geeky little world. The interesting thing, to me, is that for such a totally cerebral gift, it’s almost shockingly intimate, if you make it that way. I can’t think of very many things that are able to so completely combine the two.

  4. Mike says:

    Hey, thanks, guys.

  5. Kevin says:

    I agree with all previous comments, Mike. I’d always wondered about how crosswords get made; now I could even make one for a birthday present for Jana! You rock! I am, as always, honored to know you, sir.

  6. akdmyers says:

    I’m with B Barron; you’ve totally blown my productivity for the rest of the day because all I want to do is start designing crosswords for everyone I know. Does it get any geekier than this? What an awesome awesome idea.

  7. Mike Molloy says:

    I’m curious about why you believe contains “crap”. The database is completely human-edited, and we only accept terms verified to be in common use. What might be “crap” to you could be extremely valuable to someone else. I would be interested to see examples of what you consider “crap”.

  8. Mike says:

    Thanks for the note, Mike. You might be misinterpreting my thrust: after all, I was recommending your site, because it does such a good job of ranking acronyms by usefulness. For example, here’s a search for “SDS.” The first entry would make a decent item in a crossword puzzle; everything below it would make a crappy one.

    I’ve used acronymfinder many times in more conventional ways, and I’m glad it includes the less-common acronyms, too. I hope you keep up the comprehensive work.

  9. Sonetka says:

    This is really fascinating. (Possible birthday present for someone? I’d have to have started last year sometime, I think :)).

  10. Dana says:

    I have found another guy after your own heart, Mike:

    Man proposes via Boston Globe crossword

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