How to Make a Crossword Puzzle
wordplay
How to Make a Crossword Puzzle
In Part 3 of the series, Kevin Der and Paolo Pasco pull back the curtain on the work that goes into filling a crossword with fun and interesting entries.
DEB AMLEN: We’re making great progress on our team-built crossword puzzle. In Part 1 of the series, the constructors Ben Tausig and Finn Vigeland developed the theme, and the constructors David Steinberg and Natan Last set that theme in the grid and placed the black squares in Part 2.
In Part 3 of “How to Make a Crossword Puzzle,” our constructors, Kevin Der and Paolo Pasco, tackle filling the crossword puzzle, perhaps the most detailed effort in the process. Successfully achieving all-over interlock with words and phrases, as is required in American-style crossword puzzles, is not for the faint of heart. In addition, making sure that those entries are interesting and fun for solvers requires the strength not to fall in love with the words the constructor finds, because many of the entries may need to be replaced along the way if a section does not work.
Filling a crossword is like a dance: one step forward, two steps backward and maybe a few steps to either side. Let’s watch Mr. Der and Mr. Pasco dance the grid-filling tango.
KEVIN DER: Now that we’ve chosen our theme entries and designed a grid, it’s time to actually fill the thing. This is probably the most time-consuming part of making a crossword, so our part will be a bit longer.
PAOLO PASCO: But it’s also the most fun part! It might seem hard at first, but with enough time and practice, filling a grid can be a great opportunity to show your personality as a constructor.
DER: That resonates with me, and I’ll go one step further. Millions of people will eventually see any given New York Times crossword, so the constructors have an opportunity to carefully consider which words and ideas they want to put into the public consciousness. Ultimately, the constructors have the entire palette of language at their disposal. In an HBO interview, Will Shortz described the crossword editor as “an arbiter of what’s significant.” If the editor is the curator, then the constructor is the artist.
I’ve Got a Little List
PASCO: Very well put! We should talk about one of the main tools for controlling that palette: the humble word list. Software programs like Crossfire or Crossword Compiler allow you to create and manage word lists, which are basically dictionaries for the programs. If a word is in your word list, the program recognizes it as fair game for a crossword. Both programs give you basic word lists to start with, but you can find more refined lists (typically at a cost) from other sources. Cruciverb.com has a nice starter list for premium members, for example.
DER: My word list originally started as a few English dictionaries combined with words that had previously appeared in crossword puzzles. Since then, I’ve probably added many thousands of words by hand. I try to pay attention to interesting words and phrases that come up in everyday life and I’ll add those to a list on my phone using the Notes app. I’ll check that list first when I’m filling a grid, whether that’s a themed puzzle or a themeless.
PASCO: I have a basic word list, which I haven’t maintained a lot. The only real changes I make are when I add new, fresh words that I want to include in a crossword. I can go into the program and manually give those words high scores in my list, so they get priority when I’m filling grids. I also fill manually — I use Crossfire, but I don’t use the Autofill feature. It takes longer, but guiding the whole fill process by hand makes me feel more in touch with the crossword. It really helps me get a sense of what letter patterns work in a grid and which ones don’t.
DER: If you rely on Autofill, that guarantees you won’t have the opportunity to introduce something new that isn’t in your word list, so we discourage it. I prefer a semi-supervised approach — using software to verify the fill you have so far still works, and suggesting words that you might want to put into the grid next, while you select words by hand. During that process, I often think of words that would also work, but weren’t in my list.
PASCO: One good resource for finding words outside your word list is Onelook.com. If you have an answer like ??RK??A?, you can look it up on the site and get a list of words that match that pattern. This has bailed me out so many times when filling a grid — sometimes, all it takes is one entry you hadn’t thought of to hold together an entire section.
Quality Is Never an Accident
PASCO: In terms of the words themselves, my fill philosophy is “clean fill above everything else.” Filling by hand guarantees that every part of the grid gets my attention, so junk words are less likely to slip in.
DER: I’ll second that. How you fill the grid doesn’t matter as much as ensuring that every word in your grid is high quality. Ideally, it should seem like you purposely chose every word to be in your crossword. This is especially true for themeless puzzles, where you begin with no constraints. Most constructors try to inject fresh words and phrases, often from current events or pop culture, that have never appeared before in a crossword. Other than that, we strive for liveliness, which is ultimately a judgment that can vary among constructors and editors. Conversational phrases like “WAIT, WHAT?” or “DON’T ASK” are always fun to include in a crossword. It’s hard to describe objectively, but most constructors would agree that ESCAPE ROOM and SUBTWEET (which Paolo debuted) are more lively than, say, the unremarkable ESSENCES or, ALAN-A-DALE, which is dreaded for its overuse.
PASCO: Thanks for the shout out, Kevin! By “debuted,” we mean that it appeared in The New York Times Crossword for the first time. Constructors like debuting words, since it usually means that they’re fresh or new.
It’s tricky, because liveliness can change over time. An entry that would have been fresh a few years ago (like CRAY CRAY or SQUAD GOALS) might seem dated if it ran today. It’s not a huge deal breaker, but it’s something to keep in mind. There are worse offenses to commit when filling a grid.
DER: Made-up words are the most obvious to avoid, but so are obscurities that might be unreasonable for a typical person to know, like the names of foreign villages or minor league baseball players. I also personally avoid partial phrases and most abbreviations, especially all the midcentury government programs from history class.
But What About ‘Crosswordese’?
PASCO: Yep, T.V.A., W.P.A., REA, and all the acronyms that I tricked my U.S. history teacher into believing I’d learned. That touches on the issue of “crosswordese”: short words that appear a lot in crosswords, but are rarely seen anywhere else.
We’re talking ETUI (needle case), APSE (section of a church) and OLEO (a type of margarine), which is not to be confused with OLIO (a miscellaneous collection). I’d avoid these whenever possible. They might be needed to hold a tricky corner together, but you definitely don’t feel good about yourself when you use them. If you ever feel as if you’re forced to use an obscure word, try filling the corner again. I encourage you to not settle for crosswordese, and shoot for including familiar words.
DER: The last thing we need to mention about bad fill is the “Sunday Morning Breakfast Test,” which means that every entry in a crossword should be sufficiently family-friendly. The first New York Times crossword editor, Margaret Farrar, went further and once wrote that crosswords should avoid “death, disease, war and taxes.” To me, words strongly associated with most topics like that should never appear either in the grid or the clues.
PASCO: Absolutely. The current New York Times editor, Will Shortz, has a different take, though. When we asked him about words that should or shouldn’t be in a crossword, he wrote: “If a word or term is used in the columns of The Times, or in cultured society in general, I think it’s probably O.K. for a crossword, even if it’s touchy or slightly unpleasant. I strive to have crosswords reflect real life as much as possible. … I don’t believe in banning words, except for the very worst. And I’d be happy to abolish the term ‘breakfast test’ completely.” So, his is a pretty laissez-faire policy.
Even so, the line is still drawn at vulgarity or themes on death or disease, and for good reason. It’s important to remember that, above all, crosswords are a form of entertainment. It takes zero effort to downgrade bummer words in your word list (URINE, TUMOR, either of IDI AMIN’s names), but your puzzles will be more fun to solve as a result. Also, this should go without saying, but offensive terms should on no occasion appear anywhere in a crossword. Even if you think you can clue it in an inoffensive way, just don’t.
Start With the Most Constraints, Not the Least
DER: I think that’s a pretty comprehensive intro! Should we get started with the grid?
PASCO: Absolutely! What’s nice about this grid is that the chunks of black squares around the edges divide the grid into multiple sections, which we can fill pretty independently. We generally want to start with the section of the grid that has the most constraints. Otherwise, we’ll be adding more constraints from filling the rest of the grid, and it might just be too difficult to fill that section well, or even at all. Once the hardest section is filled, then we move to the next most constrained section, and so on until the grid is done.
PASCO: In this case, the most constrained part of the grid looks like the lower left. That’s because of the two long Down entries combined with the Z’s, which have fewer possibilities for valid words compared with other letters.
DER: Agreed. I’ve tried some sample fills, but the constraints make it tough to get both of the 10-letter Down entries to be good. I’m seeing some possibilities like COAGULATE and STIMULANTS, but those are dull. The best I’m seeing is the pair OUTMUSCLES / BRONZE COIN and neither seems that strong.
Polish That Fill Until It Shines Like the Top of the Chrysler Building
PASCO: What makes this so hard is that with long entries, there’s pressure to make them as interesting as possible. Fresh phrases generally make crosswords more interesting than long single words — that’s why Natan Last called long entries “bonus words” in Part 2 of this series. With ????Z?????, for example, I feel that an entry like SNOOZEFEST or LIL UZI VERT would be better than BREEZIEST. That’s what I mean by “personality” — the long entries you choose often reflect your vibe or style as a constructor, whether it’s academic, classical or modern.
DER: Right. And, it’s important to remember your audience when you’re filling a crossword. LIL UZI VERT might be a fun entry in a more pop-culture-y outlet like the A.V.C.X. crossword, but the general New York Times audience might not be too familiar with the name.
PASCO: You’re right — as much as I love name-dropping rappers in crosswords, LIL UZI VERT might be too much for some people. (That means SWIZZ BEATZ is out, too.)
DER: When you’re choosing two long entries to abut or stack against each other, a good rule of thumb is to leave as many possibilities as you can for the crossing entries. That’s why alternating consonants and vowels as much as possible is useful.
In the example below, notice how the grid on the right leaves a lot more possibilities than the one on the left. More words start with SO- and AM- than start with AE- and LL-.
DER: You want to avoid consecutive letters that rarely appear together, like -VK- or -PG-. There might be some entries that have that combination, but your options will be extremely limited. It’s best to leave yourself with friendly letter combinations, like -TH-, -CR- and the like. This is the part that especially comes with experience — the more crosswords you construct, the more you get a sense for which letter combinations work best.
Am I Allowed to Change Things Around to Get the Best Fill? Sure You Are.
PASCO: Great points! Another tip: If I’m not getting any good fill, I sometimes try moving black squares around to see if that helps. What if we try putting a black square under the U and take away the one under the second Z?
DER: Great idea, let’s try that. Hmm, two long entries going through Z’s is tough. Is WALTZ MUSIC a legitimate entry? Seems kind of iffy to me.
PASCO: It sounds like a thing, but I can’t find anything good to go in the nine-letter slot next to it.
DER: We could try something extreme, like flipping the grid horizontally. That way the U and Z’s would be in a less wide-open area. But I think that’s probably too different from the grid we were given.
PASCO: It feels like our problem area is the middle-left section. Going back to the grid Natan Last and David Steinberg sent us: What if we moved the black square from under the first P in PUZZLE PIECE to over that P, to break that section up?
DER: The only downside is that it creates more 3-letter words (which generally detract from the flow of words in the grid and have less potential for sparkle), but in this case the area is wide-open enough that it doesn’t bother me too much. I found a great pair that works for that: OIL FUTURES / SLEAZEBALL.
PASCO: Those are both great! PANCHO and GLO work there as Downs to finish that corner. On the other side, ???ZO could be MATZO, GONZO or BONZO. Let’s leave that open until we fill the northwest corner, so we can keep those as possibilities.
DER: O.K., now let’s move to the center. That long entry, ??ET?C??, probably doesn’t have too many choices.
PASCO: I’m seeing TIE TACKS, POETICAL and EYE TUCKS. What is that?
DER: I think an eye tuck has to do with plastic surgery.
PASCO: O.K., of those three, I like POETICAL the most. For the rest of that center, how about INCH UP / EURASIA / ROSTER / EARPIECE?
The Dreaded Duplication
DER: Hang on, EARPIECE dupes the PIECE in PUZZLE PIECE, so we probably can’t use that.
PASCO: For the people at home, why is that?
DER: Generally speaking, a word is not permitted to appear multiple times in the grid. The exceptions are prepositions and very common words as part of larger phrases. For example, our guess is that most editors would not regard HOME RUN DERBY and RUNAWAY BRIDE as a dupe. Ultimately, it’s a judgment call that depends on the liveliness of the phrases and how common the word is. PIECE, however, doesn’t seem common enough, and duplicating a word in a theme entry is especially bad.
PASCO: Oh yeah, I’m glad we caught that before filling the whole grid with that duplication. We could change that slightly to be ANTE UP / EURASIA / ROTTE?.
DER: O.K., then that long down entry could be a bunch of things. PARAPETS … how about DURSLEYS or HARD LENS?
PASCO: I like HARD LENS more, but both are good.
DER: Let’s go with HARD LENS. It’s probably better known and easier to clue in an interesting way.
PASCO: The top right has friendlier letters than the bottom left, since the constraints are easier — instead of having Down entries crossing Z’s, we have them crossing the relatively-common A and C. So, we’ll have a lot more flexibility. We should be able to put in a really flashy entry. I’m going to look through the “high priority” section of my word list: RON SWANSON … “REAL MATURE” … BRIE LARSON … trying those.
DER: Wow, I’ve really slacked off on maintaining my word list. You have some great ones there.
PASCO: Not seeing anything good for the second, adjacent long entry, though. I’m looking for something with a lot of vowels; vowel-heavy entries are generally easier to work with.
[After a while …]
DER: Maybe we can try a different actress. How about OLIVIA MUNN? I found a good entry that goes next to that, DANA SCULLY, which is topical because of the “X-Files” reboot.
PASCO: Sounds good! SPACEK can go next to that and the last three-letter entry in the corner could be MSG, PCT, PCP or MSN. We do have a lot of proper nouns next to one another, though — is that all right?
DER: Those names are pretty well known, so I think it’s worth it as long as there aren’t any obscure words crossing them. Having an obscurity cross a proper noun can be very frustrating to solvers who might not know either entry.
PASCO: So, in the ??NL? slot going across, we’d want something like MANLY instead of MENLO. That way, there’s less of a chance that solvers will be stuck where two proper names cross.
PASCO: Let’s fill the bottom right next. The corner is deceptively hard to fill, because a couple of those down entries intersect with two theme entries, so two letters in each word are already predetermined.
DER: Natan and David had suggested MEETUPS going down at the end of PUZZLE PIECE. I actually like that entry.
Fussy About Fill
PASCO: I do too! The problem is, I’m not getting a totally clean fill with it. The best I can do is ARRET / A TOAST / PEETA / SIT-IN. The “Hunger Games” character might be tough for some solvers, and ARRET is a French word that isn’t completely well known.
DER: We could try adding a cheater square — an extra black square that doesn’t change the word count — to make filling that corner a little bit easier.
PASCO: Let’s try putting one where the S is in MEETUPS. I can get a fill that’s a little better — ARMED / O’TOOLE / PEONS / SEAT.
DER: I like that better. New York Times solvers have seen Peter O’TOOLE in the puzzle more times than they have seen PEETA, and we’ve gotten rid of both the French word and SETI. Unfortunately, we now have LENA, a somewhat uncommon first name, and ERST, which is dull.
PASCO: Ultimately, the second one is cleaner, so let’s go with that. I think the cheater square is worth it — I never mind adding extra black squares, as long as they provide a cleaner fill. Think about it this way: An average solver won’t care if there’s one or two more black squares. The solver will care if a crossword is filled with unnecessary obscurities.
PASCO: ERST going down isn’t ideal, but sometimes you have to make sacrifices to fill a grid. In this case, ERST was better than the alternative (ARRET, SETI and TRAN in one corner).
Into the Homestretch
PASCO: Anyway, we should fill that top left corner next. ???AE is a rare pattern, so hopefully we’ll find something that works for that.
DER: AURAE is the only reasonable thing I can find that works there.
PASCO: I’m actually O.K. with that. If we make OGRE the Down entry in the O??E slot, and DONUTS in the ?O??T? slot, we can make the six-letter across entry a word ending in -ING. That’s great, since common word endings leave a lot of possibilities.
[A few minutes pass]
PASCO: I’ve got CELT / AVOID / INKING. That’s pretty good.
DER: It could also be CENT / NOCK instead of CELT / LOCK.
PASCO: I don’t know, NOCK feels less common. It’s good that we have possibilities, though.
DER: O.K., finishing up here. The top middle has a lot of possibilities. I like EACH / ELLA / PDF. On the left side, EOS / FILMS / FLEA is the only reasonable option I can find.
PASCO: For the bottom middle, I was kind of hoping to put LIN in there, as in “Hamilton” writer/“Mary Poppins Returns” star/all-around good boy Lin-Manuel Miranda. That works with LYNX, which includes the uncommon, high-value letter X. With unconstrained small sections like this, you’re free to add words that are as interesting as possible. Scrabbly letters like X are good ways to make corners more interesting, but they’re by no means the only way. Anyway, GIG / ARIA / LYNX should finish off the section.
DER: I’m pretty happy with the overall grid. All our long entries are good ones and there are only a few short entries that aren’t totally ideal.
PASCO: And I love the female representation in the northeast corner. Crosswords (and the names referenced in them) generally skew very male, so having three female names next to one another feels like it’s counteracting that gender disparity. Just my quick tangent, though — excellent work, Kevin!
DER: You too, Paolo! This was super fun. So there you have it, we’ve filled our grid and now we’ll hand it off to Brad Wilber and Robyn Weintraub to finish our puzzle by writing the clues.
Join us for Part 4 on July 11, when our final pair of constructors will write the clues.
Kevin G. Der has written crosswords for The New York Times since 2007. His puzzles have also appeared in other venues such as the American Crossword Puzzle Tournament, Lollapuzzoola, the MIT Mystery Hunt, and the National Puzzlers’ League convention. Follow him on Twitter @kgder.
Paolo Pasco has written puzzles for outlets like The New York Times, The Wall Street Journal, and his mom for her birthday. Recently, he became a regular contributor to the American Values Club Crossword. He also publishes crosswords whenever he can at his website, Grids These Days. Follow him on Twitter @gpaolopasco.
Top illustration by Elena Xausa.
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