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)!

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!

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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, 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.

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.

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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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