Curiouser and Curiouser: More Wordplay in Puzzling Times

Ben Zimmer
Beyond Wordplay
Published in
6 min readAug 24, 2020

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Back in June, I wrote here about how wordplay could “make our shared predicaments a bit less puzzling.” At the time, we were already well into the pandemic, and wordplay enthusiasts were trying to navigate the new social terrain, finding ways to connect virtually when social distancing is keeping us apart. Since then, the Summer of 2020 has seen an explosion of online activities that have ably filled the gap left by the cancellations of in-person tournaments, conventions, puzzle hunts, and the like.

The biggest virtual gatherings have been at crossword tournaments. While the American Crossword Puzzle Tournament was canceled this year, other competitions have moved online with great success. In my June post I talked about the first such venture, the Crossword Tournament From Your Couch in March, which attracted more than 1,800 solvers. (The lack of a registration fee certainly boosted those numbers.) Since then, two other tournaments have followed suit: Boswords on July 26th and Lollapuzzoola on Aug. 15th. These are events normally held in Boston and New York City, respectively, but without the need to travel, far more competitors joined in than they normally would have.

For Boswords, tournament directors Andrew Kingsley and John Lieb worked with AmuseLabs, the creators of the PuzzleMe solving platform, to create a smooth interface for more than 500 competitors. On Twitch, Andrew and John ran broadcasts for the dress rehearsals and the tournament itself, peppered with constructor interviews. In the finals, Paolo Pasco blazed past Erik Agard and David Plotkin to win the championship. You can still purchase the excellent puzzles from this year (as well as previous tournaments) from the Boswords website.

Lollapuzzoola, overseen by Brian Cimmet and Patrick Blindauer, was an even bigger enterprise, with more than 1,200 solvers registering to compete. Drawing on the same tech wizardry that Kevin Der developed for Crossword Tournament From Your Couch, Lollapuzzoola’s first virtual outing was a rousing success. As with Boswords, the Lollapuzzoola crowd congregated on a Twitch stream that featured interviews and lots of other fun and games between the tournament puzzles (which you can still order here).

Francis Heaney and Lorinne Lampert host a word game in between rounds at Lollapuzzoola.

When it came time for the Lollapuzzoola finals, in which David Plotkin triumphed over Jeff Davidson and Jenna LaFleur in the Express Division, everyone who tuned in to the Twitch stream was able to watch these speedy competitors go head-to-head as they filled in the championship puzzle, with all three on the screen at once. No doubt future crossword tournaments will seek to emulate this technical marvel with their own simulcasts.

The Lollapuzzoola finals on Twitch, featuring David Plotkin, Jeff Davidson, and Jenna LaFleur.

Beyond crossword tournaments, Twitch has emerged as a key medium in the social life of wordplay. You can easily fill your week with Twitch streams of collaborative puzzle solving, with hosts often sinking their teeth into tough variety cryptics rather than trying to speed-solve typical (American-style) crosswords. In my June post, I mentioned the entertaining Twitch stream of Brian Cimmet and Ryan Hecht from the “Fill Me In” crossword podcast. But there are many other enjoyable streams out there, including ones from Foggy Brume of P&A Magazine (solving insanely hard British cryptics) and Aaron Paulsen aka Scoots Baboo, who is an enthusiastic new member of the National Puzzlers League and has recently tried his hand solving the NPL’s word puzzles in verse, known as “flats.”

On Twitch, Scoots Baboo works through a variety puzzle from P&A Magazine.

Speaking of the NPL, with the group’s usual annual convention canceled, members have been organizing a series of “Conlines.” Though they’re not officially NPL events, Conlines have been dominated by the league’s intrepid puzzlers, known as “Krewe.” The first two Conlines, held over Zoom and Slack, were wonderful events, and a third one is planned for Oct. 17-18. Details are still to emerge, but if you become a member of the NPL you’ll be sure to hear about it via their mailing list and Facebook page.

Zoom lends itself well to smaller gatherings as well. Recently, crossword constructors Amanda Rafkin and Ross Trudeau held the first in a series of Zoom sessions that they call “Tipsy Puzzlers,” in which they walked through creating a puzzle with input from those in the chat (which happened to include some crossword luminaries). The rapport between Amanda and Ross made the event lots of fun, and their explanation of how to make puzzles using software (like Crossfire for the Mac) was inspiring for anyone looking to get their feet wet in crossword construction. (Ross has also been providing other public services, like handy videos explaining crossword terminology.)

The first “Tipsy Puzzlers” event on Zoom with Amanda Rafkin and Ross Trudeau.

Remember live entertainment? One of the last shows of any kind I saw in the Before Times was when Zach Sherwin brought his “Crossword Show” to New York in early March. “The Crossword Show” is a live comedy performance in which Zach leads a panel of fellow funny people through a puzzle custom-made for the show, with wonderful digressions into pop culture, trivia, and rap. With his “Crossword Show” gigs postponed, Zach is now releasing bite-sized videos with material drawn from past shows, which he calls “Crossword Show Solos.” (Did you notice the name is univocalic?)

Be sure to check out all the “Solos” so far on Zach’s YouTube channel.

Another bit of wordplay-related live entertainment that has been shelved during the pandemic is David Kwong’s show “The Enigmatist,” a unique and delightful blend of puzzles and prestidigitation. “The Enigmatist” had completed a sold-out run at New York’s High Line Hotel, and David had planned on bringing it to the Geffen Playhouse in Los Angeles in May. While we await the show’s return, David has teamed up with puzzlemaster Dave Shukan on a Kickstarter-funded project, ENIGMAS, a puzzle hunt in the form of a beautifully designed pack of playing cards. As a good measure of how much appetite there is for high-quality puzzling content, the Kickstarter was funded in 24 hours and went on to raise more than $100,000 from about 2,500 backers.

Museums have been hit hard by the pandemic as well, and that’s true for one of particular interest to the wordplay community: Planet Word, a museum devoted to inspiring the love of language, which was set to open in Washington D.C. this past spring. I serve on Planet Word’s advisory committee, and I can vouch for the terrific displays and other wordy content in the works for when the museum can finally open its doors. In the meantime, Planet Word has been sponsoring online classes, which have thus far featured Russell Ginns on “How to Create and Master Word Puzzles,” Kasha Patel on “How to Tell a Joke,” and Stefan Fatsis on “How to Win at Scrabble.” More wordplay-related goodness is definitely in the pipeline!

As I discussed in June, constructors of word puzzles have been raising money for various charities during the pandemic. Puzzlemaker extraordinaire Eric Berlin offers “The Social Distancing Puzzles,” “a suite of puzzles to solve with a partner, via Zoom or in the same room,” to anyone who donates to Feeding America. Since the launch, Eric has managed to raise more than $15,000 for the cause. Meanwhile, the team of Kid Beyond, Alison Muratore, Mike Selinker, and Sandor Weisz have been raising money for social-justice charities with puzzle suites released on Mother’s Day (Puzzle Bouquet) and Father’s Day (Puzzle Pop!), both available here.

Finally, there’s Grids for Good, a collection of 42 original crosswords and other word puzzles from an impressive array of top-flight constructors, raising money for organizations that provide coronavirus relief and fight against institutional racism. In the first ten days after launch in July, Grids for Good raised more than $50,000. As organizer Evan Birnholz tweeted when reporting on the achievement, “Puzzle folk are the best.” We couldn’t agree more.

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