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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