Bringing People Back to Puzzles After a Bad Solving Experience

About a month ago, we discussed crossword difficulty and how it can be daunting to get started in puzzles.

In that post, we shared Lloyd Morgan’s crossword difficulty matrix, a cart that allows new and unfamiliar solvers to seek out different venues based on their difficulty, ensuring they can ease into crosswords and not immediately get discouraged by a puzzle tougher than they’re ready for.

I mentioned the post to a friend of mine who isn’t terribly puzzle-savvy, and he asked, “But what about people who have already had bad experiences with crosswords and might be gun-shy about attempting them again, no matter what difficulty level is promised?”

And that’s a very fair question. How many folks do you know who try something once, and then never again after an unpleasant first encounter? I know several people who won’t touch logic problems because the grid is intimidating and they weren’t eased into the solving style. Cryptograms, Kakuro, puzzle hunts… all of them can be tainted for someone with one bad solving experience.


You might think that crisscross-style puzzles (like the one above) would be less intimidating, since they don’t have the same dense grid surrounded by clues that crosswords have, but I’ve found that folks don’t warm to those quickly. No matter how well-constructed the crisscross, it tends to remind people of activity books for kids, and no one wants to feel patronized when trying out a new hobby or giving it another go.

I do have a suggestion, though. I’ve tried this with several friends and acquaintances who had sworn off crosswords entirely, and it not only introduced them to a new puzzle they didn’t know, but opened their eyes to the possibility of more puzzle-solving in the future.

My solution was: Fill-Ins.

fillin sample

[A sample puzzle from our friends at Penny Dell Puzzles. Check out their fill-in library here!]

For the uninitiated, fill-ins utilize the same general grid style as a crossword. But instead of answering numbered clues to place the words in the grid, you’re already given the answer words, organized by word length. Your task is to place them all into the grid, using other words and letters in the grid to guide you.

Solving fill-ins helps remove the intimidation factor of crosswords in three ways.

1. No trivia or outside knowledge is required, which removes a huge burden from a solver who has probably felt overwhelmed by crossword cluing in the past.

2. It makes empty crossword grids less intimidating. Do you ever have those moments where you read three or four crossword clues in a row and you don’t immediately conjure up answers? And then you look at all those empty spaces in the grid and feel dumb? It happens. But fill-ins often have a set word to get you started, and once you start placing letters, recognizing useful crossings, and filling the grid, all that goes away.

3. Fill-ins help strengthen another skill valuable in crossword solving: letter-blank recognition. If you see B _ U _ , a regular solver instantly starts listing off possibilities: BOUT, BLUE, BLUR, BAUD, etc. But a new solver can look over at the four-letter words, scan the list, and see what fits, helping to build that mental lexicon for future solving.


After solving a handful of fill-ins, word placement goes quicker, confidence in filling in those letter blanks increases, and empty grids become fields of potential puzzle fun, not stark empty spaces.

And honestly, it’s a pretty cool feeling to make puzzles enjoyable again for someone. When I get a phone call a month or so after introducing them to fill-ins, and they ask what other puzzles are out there, or where a good place to start with crosswords might be, that’s a win.

Then, of course, I direct them to Daily POP Crosswords. Because we’re the best. (And also to other puzzle outlets like our friends at Penny Press, of course.)

Do you have any suggestions for helping restore a love of puzzles to those previously burned, spurned, or disappointed, fellow puzzlers and PuzzleNationers? Share them in the comments section below! We’d love to hear from you.


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Need Crosswords Sorted by Difficulty? Look No Further!

A quick reminder before today’s blog post:

ThinkFun’s Cold Case: A Story to Die For is available for preorder today on Amazon and the ThinkFun website!

Click here to check out our spoiler-free review!

Getting into crosswords can be daunting for new puzzlers. Maybe you’ve solved the syndicated puzzle in your local paper, or you’ve downloaded one of those fabulous apps like Daily POP Crosswords, and you’ve enjoyed, but you’re looking to expand your solving horizons.

The New York Times crossword is well-known, for sure, but has an intimidating reputation as the flagship brand. You know other companies and newspapers have crosswords, but you’re just not sure where to start.

We’ve got good news for you on that front.

A constructor and crossword enthusiast named Lloyd Morgan has assembled what he calls the crossword difficulty matrix, and it’s a thoroughly impressive launchpad for new and inexperienced crossword fans to explore a lot of terrific puzzles and crossword venues.

[Click here for a larger version!]

He originally launched a version of the crossword difficulty matrix on Reddit, and then expanded and adapted it based on feedback from fellow solvers. His goal was to create a guide for new solvers that would help them find the right puzzles and difficulty rankings for their puzzly comfort level.

Not only does he cover major outlets like The New York Times, LA Times, Wall Street Journal, USA Today, and Universal, but he also looped in Kings syndicated constructors like Joseph and Sheffer, plus some other outlets casual solvers might not even be aware of!

I haven’t really seen anything like this made available for enthusiastic solvers before, and I think he did a terrific job.

Then again, I’m not the savviest crossword solver around.

[Me, watching faster and more clever solvers posting their solve times.]

But I do know some pretty savvy cruciverbalists, so I reached out to some topnotch and experienced constructors and solvers and asked for their thoughts on the crossword difficulty matrix.

Wordplay blogger and brilliant crossword lady Deb Amlen thought it was a totally fair breakdown of puzzle difficulty, though she noted, “I still believe that if you asked 10 solvers about the difficulty of a puzzle, you will get 10 different answers.” TRUTH.

David Steinberg, editor of the Universal Crossword, thought the matrix was pretty accurate as well, though he suggested a few tweaks regarding “Universal (which has no increase in difficulty during the week for 15x15s, though the Sunday 21×21 is a bit more challenging) and maybe the Wall Street Journal (which I would consider a little easier in the early week).”

Looks like Deb’s prediction is already coming true.

I also reached out to constructor Doug Peterson, one of the most knowledgeable puzzlers in the game today, was also kind enough to offer his thoughts:

I don’t really know the Joseph & Sheffer puzzles, but I believe they’re easy, unthemed 13x13s, so light-green makes sense for those. And I think New York Magazine is Matt Gaffney, so that seems about right too. Yeah, this is well-done. I might tick up the Thursday NY Times a notch, but it varies from week to week.

He had some suggestions for other venues to include as well:

If folks are looking for something else at the Very Difficult/dark-red end of the scale, Fireball [Crosswords] sometimes gets there. They’re definitely a “red” venue. The Inkubator I’d put in that middle yellow/Wednesday area for their themed stuff. And AV Club is literally the entire range above “Very Easy.”

I did ask one or two other puzzlers, but they hadn’t had the chance to reply by press time, so we’ll probably revisit this topic in the future (especially if Lloyd offers an updated version).

But in the meantime, I want to give some well-deserved kudos to Lloyd for this marvelous resource for new solvers. Not only does it include a lot of terrific outlets, but it offers a terrific stepladder of difficulty for them to find ever-increasing challenges whenever they’d like!

Thank you to Lloyd, as well as the marvelous constructors and puzzly folks who offered their thoughts. You’re all part of a brilliant, vibrant, and welcoming crossword community.

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