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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