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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Publish More Women!

That was the message received loud and clear by attendees at the American Crossword Puzzle Tournament last year if they saw Erik Agard’s t-shirt. The future ACPT champion was amplifying a call that has resonated throughout the puzzle community for years now.

And yet, puzzles are often still regarded as a boys’ club.

Despite the fact that Margaret Farrar got the ball rolling. Despite the fact that Maura Jacobson contributed a puzzle to each of the first 34 ACPT tournaments and created over 1400 puzzles for New York Magazine. Despite a grand tradition of female innovators, tournament champions, and topnotch constructors that continues to this very day.

This topic once again took center stage recently when Will Shortz, gatekeeper for The New York Times crossword, posted his thoughts on the subject online:

Periodically I get asked, “Why aren’t more female constructors published in the New York Times?” And I always think, “Well, we don’t get a lot of submissions from women.” But until now I’ve never counted.

So this afternoon I counted. I looked through 260 recent submissions … and counted 33 by female constructors. That’s a little under 13%.

This figure is in line with the percentage of female constructors we publish. Last year, according to the stats at XwordInfo, 13% of the crosswords published in the Times were by women. So far this year the figure is slightly better — 15%.

Why this number is still so low, I don’t know.

In positive news, the number of new female constructors is significantly higher. In 2016, 31% of the 26 contributors who made their Times debut were female. In 2017, 19% were female. So far this year 27% have been female. XwordInfo lists all the names.

Our goal is to be inclusive. We want the Times crossword to reflect the lives, culture, and vocabulary of the people who do it, and having more female-made puzzles would provide better balance.

Still for us to publish more women constructors, we need to receive more puzzles by women. That’s the bottom line.

Our policy is open submissions. If you’re a woman who’d like to get into crossword constructing, we’d welcome your contributions, and we’ll be happy to work with you to get you published.

Reactions across the puzzle community have been mixed, but a number of people found Will’s response lacking. They asked what actual steps would be taken in order to encourage women and other underrepresented groups. Would there be additional support from the NYT for these sought-after constructors? Or would the status quo remain precisely that?

Those are questions worth asking. After all, the Times has been celebrating its 75th anniversary for the last year and a half with celebrity guest constructors. But how many of those celebrity collaborations have been with female constructors?

Three. That’s a project with huge visibility and mainstream media crossover potential, and the number is three.

And speaking of media crossover, it wasn’t that long ago — less than two years, actually — that the divisive clue “Decidedly non-feminist women’s group” for HAREM appeared in the NYT. Ruth Gordon wrote a brilliant piece in Slate highlighting how cluing standards at the Times could be exclusionary:

“Hateful” and “awful” may seem a bit harsh for what reads like a lame attempt at cheekiness. But the clue is certainly tone-deaf. And it’s not the first time a puzzle’s un-PC cluelessness has annoyed people. In 2012, the answer ILLEGAL was clued with: “One caught by the border patrol.” The offensive use of illegal as a noun set off a brouhaha that made its way to Univision.

And in November, Shortz issued a mea culpa for the clue “Exasperated comment from a feminist.” Answer: MEN — presumably with an invisible exclamation point and flying sweat out of a Cathy comic.

So, how has the NYT crossword been doing over the last two years?

We can turn again to the insightful Erik Agard for context. While guest-posting on Rex Parker’s puzzle blog, Erik took a moment to celebrate and spread the word about Women of Letters, the marvelous 18-puzzle charity project we also discussed a few weeks ago:

It’s also a lot of women! In fact, there are more woman-constructed crosswords in this collection than there have been published by the New York Times so far this year. Those who fail to see the urgency in closing the gender gaps in crossword constructing and editing often posit that ‘you can’t tell the difference between a crossword written by a woman and one written by a man’ (ergo, whether women are equally represented has little bearing on the end product, so why should we care).

The puzzles in Women of Letters disprove that thesis in a big way, through the dizzying array of less-traveled roads explored by themes, grids, and clues alike. From the juiciest marquee answers in the themelesses to the simplest choice of referencing a legendary actress by her accolades and not just [Bond girl], the collection never ceases to be a breath of fresh, inimitable air. (As the young people say: “Your fave could never.”)

That comment was posted on April 29th, and yes, as of April 29th, the New York Times crossword had published 17 puzzles from female constructors (including male/female collabs). That’s 17 out of 119 puzzles for the year, or 14.3%.

Erik helpfully provided some other statistics for the sake of comparison:

  • Crosswords With Friends: 33/119 = 27.7%
  • The Los Angeles Times: 31/119 = 26.1%
  • American Values Club Crossword: 3/18 = 16.7%
  • Chronicle for Higher Education: 2/16 = 12.5%
  • Wall Street Journal: 9/99 = 9.1%
  • Fireball Crosswords: 0/19 = 0%

It’s also worth pointing out that, as of April 29th, our Daily POP Crosswords app stood at 87/119, or 73.1%.

If you update the listings up through May 15th, Daily Pop Crosswords published 95 puzzles by women over 135 days. March alone featured 21 puzzles by women across 31 days. Heck, in February, only two puzzles the entire month were constructed by men. (Er, man, to be more specific. The same chap constructed both.)

But those aren’t the only numbers worth celebrating. Our friends at Penny/Dell Puzzles maintain an impressive publication rate for The Crosswords Club subscription service. They publish six puzzles a month, so from January to May, that’s 30 puzzles, and 16 were constructed by women (including three collabs). The January issue was all female constructors.

That’s no surprise, honestly, given the company. At Penny/Dell Puzzles, women constitute the majority of not only puzzle editors, but upper management as well.

So, forgive me if I come off as flippant, but when Will Shortz asks, “Why this number is still so low?”, I have to ask why as well.

Because the constructors are out there, right now, doing tremendous work.


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