5 Questions for Crossword Constructor and Wordplay Blogger Deb Amlen

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!

It’s all about exploring the vast and intriguing puzzle community by talking to those who make puzzles and those who enjoy them! (Click here to check out previous editions of 5 Questions!)

And we’re excited to welcome Deb Amlen as our latest 5 Questions interviewee!

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[Deb in the center, flanked by her fellow Musketeers.]

Deb is a talented crossword constructor, but these days, it’s more likely you know her for her role as the head writer and senior editor of Wordplay, the crossword blog and educational/humor column associated with The New York Times crossword puzzle.

One of the most public faces associated with the crossword, Deb entertains and informs across both the blog and its associated Twitter account, as well as hosting a live-solving show on YouTube with fellow constructor Sam Ezersky and celebrity guests!

Deb was gracious enough to take some time out to talk to us, so without further ado, let’s get to the interview!


5 Questions for Deb Amlen

1. How did you get started with puzzles?

Word games like “Ghost” were always my favorite things to play when I was a child, but I didn’t really get into puzzles until I was a young adult. I watched my father solve the New York Times crossword when I was really young, but I didn’t start solving on my own until I bought myself a subscription to New York Magazine after college and discovered Maura Jacobson’s puzzles.

I started constructing crosswords when my own kids were young because, as a stay-at-home mom, I desperately needed a creative outlet that didn’t involve Pokémon or Elmo. I read everything I could about puzzle making and learned how to make crosswords from Nancy Salomon. Nancy has mentored hundreds of constructors to publication.

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2. As the flagbearer for crosswords in the public eye, The New York Times crossword is often the most scrutinized when it comes to cultural sensitivity regarding entries and clues, and more than once, that has depicted the Times puzzle in an unflattering light.

As a very public figure for the brand — not to mention the de facto social media gatekeeper — this puts you in the unenviable position of being between the audience and the editorial team. How do you handle these situations, and as an enthusiastic solver yourself, how do you think the Times is doing in this arena?

The crossword does get a lot of flack, doesn’t it? Honestly, some of it is warranted, some of it is not.

There is definitely a need to bring the flagship puzzle into the 21st century in terms of diversity and representation. Like most large companies, however, sometimes change happens slowly at The New York Times.

A lot of work is being done by the company and the puzzle editors behind the scenes, though, to increase diversity on their team and to be more aware of content that is inflammatory, and I think the recent puzzles reflect that. They have a ways to go, but the conversation is active and ongoing, and I’m very optimistic about the future of the crossword.

As far as social media goes, people tend to conflate “the Wordplay Twitter account” with “Everything The New York Times Does With Regard to Puzzles and Games.” So, since I run the Wordplay account and the puzzle editors are not really on social media, I tend to be the target of people’s complaints, which is hilarious because I’m just the columnist. Luckily, The Times has allowed me to expense a thick skin, so I’m doing OK. When I’m not, I take a break from social media, which I highly recommend and think everyone should do.

On the other hand, most people are well-wishers and are a lot of fun. They tweet their solving victories to me and I give them a gold medal emoji, which people really respond to. It’s very satisfying to be able to lift people up and encourage them, especially on social media, which can be very negative.

3. For the 75th anniversary of the New York Times crossword, constructors and celebrity guest puzzlers collaborated on numerous puzzles. Which celebrity constructors surprised you the most with their work, and who would you like to see as guest constructors in the future?

I’m not sure I was surprised by this, but I believe that Rachel Maddow’s crossword was one of the most popular, most downloaded puzzles we’ve ever had. Neil Patrick Harris’s puzzle had a very cool trick to it. And I can’t leave out the one I did with Natasha Lyonne, who was just brilliant to work with.

[Author’s note: When asked about her puzzle, Natasha said, “Working with Deb Amlen to create this puzzle has quite literally been a lifetime highlight for me.”]

4. What’s next for Deb Amlen?

Dinner, probably.

5. If you could give the readers, writers, aspiring constructors, and puzzle fans in the audience one piece of advice, what would it be?

Enjoy yourself. This is not like sitting down to take the SAT; it’s a game. And games should be fun. Life is too short to sweat the crossword.


A huge thank you to Deb for her time. You can follow her on Twitter for updates on her puzzly and creative endeavors, and be sure to check out her work on the Wordplay blog and her very entertaining live-solving videos on YouTube. We can’t wait to see what she cooks up next.

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ACPT 2018 Wrap-Up!

The 41st annual American Crossword Puzzle Tournament was this weekend, and puzzlers descended on the Stamford Marriott Hotel once again to put their puzzly skills to the test in what is lovingly known as “the Nerd Olympics.”

The tournament takes place over two days, with six puzzles to solve on Saturday, followed by one on Sunday. Then the top three finishers in the A, B, and C brackets solve the championship puzzle on whiteboards in front of the audience.

On Friday and Saturday night, there are often puzzle events, demonstrations, and panels by top puzzlers and figures in the puzzle world as well.

I made the journey down to Stamford myself Saturday morning, arriving with plenty of time to spare to prep our spot in the puzzle marketplace and say hello to friends and puzzly acquaintances. This year, I was joined at the Penny Dell Puzzles booth once again by my friend and partner-in-promotion Stacey Scarso.

The Penny Dell crew had a terrific setup as always, with a metric buttload of magazines to give away, including copies of The Crosswords Club and several flavors of Tournament Variety, Master’s Variety, and Dell Sunday Crosswords. They were also running a kickass promotion offering half-price on a year’s subscription to Crosswords Club, which is a great deal.

Plus we had a terrific sample puzzle for the Daily POP Crosswords app, constructed by the marvelous Angela Halsted! You can click this link for the answer grid AND a bonus offer for anyone who missed our ACPT tournament puzzle!

PLUS we held a contest to win a bundle of PDP puzzle swag, including a mug, a tote bag, an umbrella, and a bunch of puzzle magazines! All you had to do was solve a marvelous crossword variant puzzle cooked up by the folks at Penny Dell. (Though I did have a hand in writing some of the clues.)

And, yes, in their downtime between tournament puzzles, many competitors DO solve other puzzles.

At 9 AM, the tournament was two hours away, but the marketplace was up and running. There were puzzle magazines galore from the Village Bookstore (as well as a table of Merl Reagle’s puzzle books), a booth loaded with Nathan Curtis’s various puzzly projects, and ACPT-themed jewelry, key chains, teddy bears, magnets, and other items from All of the Things.

As competitors readied themselves for the day’s solving, I had plenty of time to see friends of the blog like Crosswords Club editor Patti Varol, crossword gentleman Doug Peterson, constructor Joanne Sullivan, and Penny Press variety editor Keith Yarbrough!

Perhaps the best part of attending the tournament is getting to chat with so many members of the puzzle community in one place. There were first-time attendees and enthusiastic rookies; apparently, contestants ranged in age from 17 to 92(!), and there was a 90-year-old rookie competing this year!

There were long-time puzzle fans who have been competing at ACPT for years, if not decades, many of whom were decked out in puzzle shirts, puzzle scarves, and other grid-heavy accoutrements.

One of the attendees even offered to buy the Crossword Puzzle Junkie shirt off my back! I assured him that that would work for him and literally no one else in attendance.

But I digress.

Many of the top constructors in the business were there, names like David Steinberg, Evan Birnholz, Joon Pahk, Peter Gordon, and more, along with former champions and first-rate competitors like Dan Feyer, Tyler Hinman, Howard Barkin, Ellen Ripstein, and Stella Zawistowski.

Getting to connect faces and personalities with names I know from tournaments like the Indie 500 is a real treat, and so many of the people in the puzzle world are genuinely nice, funny individuals. Not only that, but I also got to meet several fellow trivia fiends from the Learned League community!

The two hours before showtime passed quickly, and soon, the marketplace emptied and the ballroom filled as competitors took their seats for Puzzle 1.

Attendance jumped again this year, which meant not only was the main ballroom absolutely jam-packed with competitors, but an overflow room was needed to accommodate the nearly 700 solvers in Stamford!

When Puzzle 1 arrived, most competitors found Tracy Gray’s puzzle to be quick and fair. One solver in particular, constructor Erik Agard, delivered an absolutely blistering time, solving the puzzle in under 2 minutes! (A feat not seen since Dan Feyer did so in 2015.) It immediately rocketed Erik to the top of the leaderboard in impressive fashion.

Puzzle 2, constructed by prolific puzzler Zhouqin Burnikel, surprised some solvers with its difficulty. Then again, Puzzle 2 has been on the tougher side for at least the last few years, but I think many solvers forget that, given how legendarily difficult Puzzle 5 is every year. It’s easy to forget other puzzles can offer quite a challenge along the way.

Puzzle 3 was constructed by Mike Shenk, and served as a well-received palate-cleanser before the lunch break. Solvers scattered to the four winds in order to grab a bite to eat before returning by 2:30 for Puzzle 4.

[Even empty, all the dividers make the room feel packed…]

And what a Puzzle 4 it was. Constructed by Damon Gulczynski, this puzzle had a visual element that tripped up several top competitors. (An unclear blurb “explanation” didn’t help matters, and several competitors told me they would’ve been better off with no blurb at all.)

The judges were forced to actually explain the puzzle before competitors began Puzzle 5. It was a disappointing way for the second half of the tournament day to kick off.

Not only that, but one solver was mistakenly given Puzzle 5 to solve INSTEAD of Puzzle 4. He managed to solve it in the shorter time allotted, but couldn’t fairly solve Puzzle 4 afterward because of the explanation. I haven’t been able to follow up and find out what exactly happened to his score.

Finally, after the unexpected drama of Puzzle 4, it was time for Puzzle 5. This year, constructor Joel Fagliano did the honors, and according to competitors, it was as challenging as expected, really putting the craftiness and keen wits of the solvers to the test. (Apparently, computer solving program Dr. Fill failed to complete puzzle 5, one of its few slip-ups in an otherwise impressive year for the program.)

After the diabolical Puzzle 5, competitors closed out the day with Puzzle 6, constructed by Lynn Lempel, and declared it both fun and fair. The competitors dispersed to rest their brains (or solve more puzzles). We packed up the Penny/Dell table and headed for home.

And although I wasn’t present for Sunday’s tournament finale, I continued to get updates from friends and fellow puzzlers.

Puzzle 7, constructed by Patrick Berry, was what you might expect from a constructor of his caliber: elegant fill, very little crosswordese, and great fun.

Erik Agard remained at the top of the leaderboard, having kept a great solving pace after his outstanding performance on Puzzle 1 — a nice redemption for him after a heartbreaker last year, when an error dropped him out of finals contention after a strong performance overall.

So the final three would be Erik, Dan Feyer (7-time champ), and David Plotkin (a familiar name in the top ten).

Thankfully, this year, there was no repeat of last year’s flub where the B-level finalists got the A-level clues or anything like that. And there were no distinct time advantages among the top solvers.

It was simply a match-up of some of the fastest, sharpest puzzlers. (Including 2 rookies in the C-level final!)

You can watch the final puzzle being solved below, courtesy of Ben Zimmer:

Erik Agard would complete the puzzle first, solving it in under 5 minutes. By comparison, huge swathes of Dan and David’s grids were still empty at this point. It was a stunning showing for a very well-liked member of the puzzle community!

Dan Feyer would wrap the puzzle up in 9 minutes, with David Plotkin following at around 13.

As he had done all tournament, Erik solved with incredible speed and precision, claiming his first tournament victory!

And it was a strong showing for many other familiar names! Doug Peterson placed 14th (up from 18th last year!), David Steinberg placed 23rd (up from 28th!), and Patti Varol placed 74th (up from 103 last year!) out of a field of almost 700 participants. (And even with one eye tied behind his back, Keith Yarbrough managed an impressive performance as well!)

[I wonder how many competitors this tweet applies to…]

It’s always great fun to spend time with fellow puzzlers and wordplay enthusiasts, immersing myself in the puzzle community and enjoying all the charm and camaraderie that comes with it.

We’ll see you next year!


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