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.

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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.

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[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.

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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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Have you checked out our special summer deals yet? You can find them on the Home Screen for Daily POP Crosswords and Daily POP Word Search! Check them out!

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5 Questions for Crossword Constructing Duo May Huang and Kevin Trickey!

Welcome to 5 Questions, our recurring interview series where we reach out to puzzle constructors, game designers, writers, filmmakers, musicians, artists, and puzzle enthusiasts from all walks of life!

This feature is all about exploring the vast and intriguing puzzle community by talking to those who make puzzles and those who enjoy them.

And this marks the fourth edition of a new series of interviews where we turn our eyes to the future of crosswords. Instead of interviewing established talents in the field, I’ve been reaching out to new and up-and-coming constructors and asking them to share their experiences as a nascent cruciverbalist.

And we’re excited to welcome May Huang and Kevin Trickey as our latest 5 Questions interviewees (and our first duo interview)!

Kevin and May - crossword background

For many modern constructors, making crosswords isn’t simply about building grids or writing clues. It’s also about contributing to the greater crossword community in a meaningful way.

And you’d be hard-pressed to find two people making bigger strides in that direction than constructor May Huang and programmer Kevin Trickey. They have launched their own free puzzle site, Crossworthy, to share a new puzzle every week, and May’s puzzles have found their way into outlets like The Inkubator.

But they’ve gone above and beyond by creating a free-to-use crossword construction tool, Crossworthy Construct. With the price of quality crossword-constructing software often proving a major hindrance to new puzzlers, Crossworthy Construct is an amazing resource for any aspiring cruciverbalist to try out.

May and Kevin were gracious enough to take some time out to talk to us, so without further ado, let’s get to the interview!


5 Questions for May Huang and Kevin Trickey

1. How did you get started with puzzles?

In the early months of quarantine, May started playing the NYT minis and eventually began making her own minis that she would send out to friends and family throughout the month (her newsletter was called “May’s Minis”). As Kevin watched May iterate through fills on Microsoft Word, he started writing an algorithm that could churn out larger grids more quickly. In June, we started Crossworthy, a website for publishing our algorithm-generated and hand-made grids.

Unlike some constructors we know, we didn’t start out as avid crossword players before starting to make our own puzzles. But the creative and technical challenges of crossword construction align with our mutual interests — May is a literary translator who enjoys wordplay, while Kevin is a casual programmer who fancied a challenge. Now, of course, we love both playing crosswords as well!

2. You have your own puzzle website (and editing software!), in addition to publishing through outlets like The Inkubator. As you start to interact with the puzzle community at large, what have you learned along the way? What has been the most surprising part of the process for you?

When we first started making puzzles, we didn’t expect this hobby to really take off, but it really has! We went from constructing puzzles using Microsoft Word (a good learning experience, but not sustainable) to developing our own software that streamlines our construction process.

Along the way, however, we were surprised to see how many resources already exist — tools and communities we wish we had known about sooner! We sometimes tweet about our construction questions and we’re always heartened by how instantly helpful fellow constructors can be. The best thing we’ve learned is that the crossword community can be a very kind and welcoming place.

Crossworthy Construct page

[Crossworthy Construct, May and Kevin’s crossword custom editing
software. Click here to check it out for yourself.]

What, in your estimation, makes for a great puzzle? What do you most enjoy — or try hardest to avoid — when constructing your own?

A great puzzle, to us, is both personal and accessible; it should have words and clues that really resonate with the constructor, as well as elements that will speak to any player. Because we have different interests, however, we often clash over clues.

For example, most of May’s pop culture clues fly over Kevin’s head, whereas the biology terms Kevin tends to include are equally obscure to her. In this way, we keep each other in check, and try to produce well-balanced puzzles. Nonetheless, we’re still rookies in the field: we’re still learning about what makes a theme set stand out and which words make for sparkly fill.

3. Do you have any favorite crossword themes or clues, either your own or those crafted by others? Who inspires you as a constructor?

Recent puzzles we’ve really enjoyed include Paolo Pasco’s “Busting Moves” puzzle (January 3rd, 2021) as well as Matthew Stock’s “Karaoke Bars” (February 21, 2021). Malaika Handa’s daily 7×7 project is fantastic, and Evan Birnholz’s meta puzzle “5×5” in the Washington Post was super eye-opening. We’re inspired by too many constructors to name — Barbara Lin, Caitlin Reid, Natan Last, Ross Trudeau, Kam Austin Collins…the list goes on!

We tend to like puzzles with themes that make us smile, and reveal an aspect of the constructor’s personality. Some of our own puzzles that fall into our category include “Valentine Poem,” whose theme words spell out a crossword-themed love poem, and “A President’s Ponderings,” a puzzle that includes presidential puns in its theme set.

crossworthy valentine

4. What’s next for May Huang and Kevin Trickey?

While we plan to continue publishing weekly puzzles on Crossworthy every Sunday, we also hope to start publishing more puzzles in other venues (May has a puzzle coming out from the Inkubator soon!).

We’re also spending a lot of time building out new features for Crossworthy Construct, our own free construction software. Our goal is to reduce the barriers to entry for new and aspiring constructors like us. Currently, anyone can use our site to construct their own puzzles, and we’d love to hear from as many people as possible about their ideal construction software.

5. What’s one piece of advice you would offer fellow solvers, aspiring constructors/setters, and puzzle enthusiasts?

Kevin’s advice: Find an angle that interests you the most. Like everything else in life, crossword constructing is the convergence of many disciplines, and you can choose to play to your strengths. For me, it was the technical challenge of coding that got me started, and it’s kept me invested a year later.

May’s advice: Don’t be discouraged if you have trouble solving the NYT puzzle; in fact, look beyond the NYT! There are so many more crossword publication venues and indie sites out there making great puzzles. There are many diverse voices in the crossworld and you can definitely be one of them.


A huge thank you to May and Kevin for their time. You can follow them on Twitter for all of their crossword endeavors, and be sure to check out their website Crossworthy to solve puzzles and try out their crossword constructing software! I cannot wait to see what they cook up next!

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The PN Blog 2020 Countdown!

It’s the final blog post of the year, so what do you say we revisit all of 2020 with a countdown of my ten favorite blog posts from the past year!


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#10 Farewell, Keith

I don’t mean to start off this countdown on a sad note by mentioning the loss of fellow puzzler and Penny Dell colleague Keith Yarbrough. Writing this post was incredibly difficult, but I am proud of how it turned out. It served as a valuable part of my healing process, allowing me to immerse myself in nothing but good memories of my friend. Giving other people the opportunity to know Keith like I did was a worthwhile experience.

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#9 Tap Code

Exploring the different ways puzzles have been involved in historical moments, either as anecdotes or key aspects, is one of my favorite parts of writing for PuzzleNation Blog. But it’s rare to have a historical story about puzzles that tugs on your heartstrings like this one. The way the Tap code served to keep the spirits of POWs high — and the way that codes and spycraft helped a husband and wife endure the hardships of separation — made this a post with a lot of depth and humanity.

#8 Holiday Puzzly Gift Guide

Every year, one of my favorite activities is putting together our Holiday Puzzly Gift Guide. I get to include the best products sent to me for review by top puzzle and game companies, mix in some of my own favorites, and draw attention to terrific constructors, game designers, and friends of the blog, all in the hopes of introducing solvers (and families of solvers) to quality puzzles and games.

#7 Crossword Commentary

There’s more to writing about crosswords than simply solving puzzles and unraveling clues, and that was especially true this year. The social and cultural aspect of crosswords came up several times, and it’s important to discuss these issues in an open, honest way, even if that means calling out a toxic presence like Timothy Parker, or even questioning the choices of the biggest crossword in the world to hold them accountable.

Whether it was exploring representation in crossword entries and cluing or continuing to debate cultural sensitivity in crossword answers in the major outlets, we took up the torch more than once this year because it was the right thing to do.

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#6 Best Puzzle Solvers

Last year, we began a series of posts examining the best puzzle solvers in various realms of pop culture, and I very much enjoyed combing through the worlds of horror movies and television for the sharpest minds and most clever problem solvers.

This series continued in 2020, as we delved into literature (for adult readers, young adult readers, AND younger readers, respectively), as well as compiling a list of the worst puzzle solvers in pop culture. We even graded the skills of different fictional crossword constructors to see who was representing the best and worst in puzzle construction in media!

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#5 Crossword Bingo

One of the most clever deconstructions of the medium of crosswords I came across this year was a bingo card a solver made, highlighting words and tropes that frequently appear in modern crosswords. It was a smartly visual way of discussing repetition and pet peeves, but also a sly bit of commentary. So naturally, we couldn’t resist making our own Crossword Bingo card and getting in on the fun.

#4 Pitches for Crossword Mysteries

Hallmark’s Crossword Mysteries series was one of the most noteworthy crossovers between puzzles and popular media last year, and that continued into this year with the third Crossword Mysteries film, Abracadaver. But we couldn’t get the idea of a fourth film — still promised on IMDb and other outlets — out of our heads, so we ended up pitching our own ideas for the fourth installment in the franchise. Writing this, no joke, was one of my favorite silly brainstorming sessions of the entire year.

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#3 The World of Puzzles Adapts

Even in a post celebrating the best, the most satisfying, the most rewarding, and the most enjoyable entries from 2020, you cannot help but at least mention the prevailing circumstances that shaped the entire year. 2020 will forever be the pandemic year in our memories, but it will also be the year that I remember puzzlers and constructors adapting and creating some of the most memorable puzzle experiences I’ve ever had.

From the initial experiment of Crossword Tournament From Your Couch to the creation of the Boswords Fall Themeless League, from tournaments like Boswords and Lollapuzzoola going virtual to the crew at Club Drosselmeyer creating an interactive puzzly radio show for the ages, I was blown away by the wit, ambition, determination, and puzzle-fueled innovation brought to the fore this year.

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#2 Eyes Open

Earlier this year, we made a promise to all of the people standing up for underrepresented and mistreated groups to do our part in helping make the world better for women, for people of color, and for the LGBTQIA+ community. We launched Eyes Open, a puzzle series designed to better educate ourselves and our fellow solvers about important social topics. And that is a promise we will carry into 2021. We hope that, in some small way, we are contributing to a better, more inclusive world.

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#1 Fairness

Part of the prevailing mindset of PuzzleNation Blog is that puzzles can and should be for everyone. They should be fun. And they should be fair.

So this year, two posts stood out to me as epitomizing that spirit. The first was a discussion of intuitive vs non-intuitive puzzles, which I feel is very relevant these days, given the proliferation of different puzzle experiences like escape rooms out there.

The second, quite simply, was a response to a friend’s Facebook post where she felt guilty for looking up answers she didn’t know in a crossword, calling it “cheating.” I tried to reassure her there was no such thing as cheating in crosswords.

And since I couldn’t decide between these two posts for the top spot in our countdown, I’m putting them both here, because I feel like they represent a similar spirit. I hope you feel the same.


Thanks for spending 2020 with us, through brain teasers and big ideas, through Hallmark mysteries and Halloween puns, through puzzle launches and landmark moments. We’ll see you in 2021.

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Happy One Year Anniversary, Crossword Puzzle Collaboration Directory!

It’s funny how crosswords can seem like a solitary pursuit — and are often depicted as such in pop culture — and yet, there’s such a sense of camaraderie that comes with being a solver.

I talk a lot about the PuzzleNation community and my fellow PuzzleNationers, or about the puzzle community in general, because it’s one of my favorite aspects of being a puzzle guy.

Whether it’s engaging in a puzzly activity with friends (like an escape room or a D&D adventure), hanging out with fellow puzzlers at events like the American Crossword Puzzle Tournament (registration is open now!), or just teaming up with a pal to crack a particularly devious puzzle or brain teaser, those moments of shared experience are as encouraging as they are welcome.

So it’s very cool to see one of the newer parts of the puzzle community celebrating its one-year anniversary: The Crossword Puzzle Collaboration Directory.

This Facebook group is part gathering place for established and aspiring constructors and part resource for constructors of all skill levels.

Over the last year, people have posted and shared information about everything from grid construction, editing programs, and cluing advice to networking, test-solving, and encouraging feedback.

[Some constructors even offer visual aids when answering questions!]

Inexperienced and aspiring constructors meet and collaborate with established names. Obstacles, problems, and questions are handled with equal care and support. Heck, some constructors have even posted rejection notices they’ve received in order to share the valuable feedback it contains.

And some members of the group have greater ambitions for the Crossword Puzzle Collaboration Directory, hoping to encourage more constructors from underrepresented groups to construct and submit their puzzles, bringing a genuine level of equality and equal representation in the world of puzzles.

It’s a place to learn, to network, to grow, to celebrate one’s successes, and learn from one’s setbacks. One of the regular visitors of the group even managed to cross off one of her New Year’s resolutions last year by submitting a crossword to The New York Times, thanks in part to the resources and support provided by this marvelous group of people.

And that’s definitely something worth celebrating.


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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!