This month, we speak with lawyer, theater enthusiast, and not-the-reality-TV-star Maddy Ziegler (she/her). Maddy lives in Madison, Wisconsin with her cat, Fred.
Maddy! Thanks for saying yes to this Constructor Spotlight feature. Tell us how you got into crosswords.
I always solved puzzles casually, and eventually worked my way up to being able to solve harder puzzles. I can’t remember what inspired me, but I did give constructing a brief try in 2019. I couldn’t really get anything going, and the construction software quickly joined crochet hooks, embroidery kits, and scrapbooking supplies as a failed hobby expense.
Then, at the beginning of 2024, I decided to start the year by getting a New York Times crossword streak going. A couple weeks into the year, I was bowled over when a constructor byline was someone I knew (Hemant Mehta, a professional acquaintance). That got me thinking about constructing again, and I think there were just better free resources available this time around – spread the word(list) in particular. I was up and running really quickly and haven’t stopped!
What do you like about crosswords?
The word that comes to mind when I think about crosswords is “satisfying.” It’s a satisfying accomplishment to finish solving a puzzle, but also on a smaller level, it’s satisfying to finally figure out a hard clue or catch on to a theme. I’ve also been finding it satisfying to speed-solve and go for a new personal best or make the daily Puzzmo leaderboard.
Constructing is basically solving a puzzle, too, and getting to that last section and finding fill that works is the ultimate satisfaction!
I also love going to crossword tournaments; I’ve met so many great people. I just attended my first Lollapuzzoola and had a great time! And I’m very excited to be going back to the Midwest tournament in October after having to miss it last year.
Woohoo, see you there! 🙌
Speaking of tournaments, I remember meeting you at ACPT in 2024. We ran into Patti Varol, who recognized your name because of a few emails she had received – apparently you (almost) share a name with a reality television star, and some LAT solvers thought that she was making the puzzles! I bet you have some stories…
People may be disappointed to learn that I have not been in even one Sia music video, unlike the talented dancer and actress Maddie Ziegler. I haven’t been harassed by anyone on Instagram wanting to turn the username @maddyziegler into a “Dance Moms” fan account lately, but that used to happen pretty regularly. The high point was when Elle magazine once tagged me in a tweet instead of her. I think she got famous enough that people mostly learned how to spell her name correctly, although there are a few NYT commenters (in addition to LAT solvers) who are under the impression she constructs crossword puzzles. (If she’d like to do so, I’d love to collab).
Yessss. I’ll keep my eye out for a Maddy Ziegler & Maddie Ziegler byline.
Where are you published?
I’ve been lucky enough to be pretty much everywhere! The New York Times, LA Times, USA Today, Universal, AVCX, Apple News+, Defector, and The Atlantic.
Themed or themeless?
I’m primarily a themeless constructor. This is largely because I am not very good at coming up with themes. But I do generally just enjoy themelesses more. I’ve found I like uncovering a fun colorful phrase or unraveling a great tricky clue more than working out a theme (although of course the best themed puzzles allow you to do those things, too).
How do you come up with your constructing ideas?
Luckily, I developed puzzle-brain soon after starting constructing, and now something pings in my head when I come across a phrase that might make good a themeless seed or theme revealer. I keep lists of both on my phone that I go to when I start constructing because coming up with something in the moment never works for me!
Please share some of your greatest hits with us.
Looking over my published puzzles, some favorites are:
(All themelesses!)
I know you love theater, tell us more about that. Do you have a favorite show?
I do love theater and I attend a lot of shows. I go to New York at least once a year to see a bunch of shows. There’s just nothing like the energy of a live performance – being in the same room with a talented group of people pulling off something amazing live, right in front of you.
My favorite show is “Natasha, Pierre, and the Great Comet of 1812.” Unfortunately, I wasn’t able to see it in New York, but I was lucky enough to see it near home. One of the very first regional productions was in Madison! Finally getting to experience the show live after dying to see it for years was really special.
What advice would you give to newer constructors?
If you can find the patience for a whole lot of trial and error, you can do pretty much anything!
Any favorite crossword resources to shout out?
Aside from the usual suspects, my secret is that Wiktionary’s “derived terms” sections are the best places to mine question-mark clues.
Tell us more about your day job. Did you always want to be a lawyer? What was law school like? (How accurate is “Legally Blonde”?)
I am not one of those people who always wanted to be a lawyer. I went to law school because I didn’t know what I wanted to do for a job after college, but I was good at school, so I thought I might as well just go to school some more. I don’t recommend this! I got very lucky that I found the organization I work for during law school and had an internship turn into a nontraditional job that suits me very well.
I work on our non-litigation legal advocacy, attempting to resolve violations of the separation of church and state that people from all over the country report to us. I get to help people get a pretty immediate resolution to a problem, which is really fulfilling.
Oh, and “Legally Blonde” is 100% accurate.
I knew it. Lastly, tell us about Fred (great name, btw).
Freddy is named after Captain Frederick Wentworth in “Persuasion,” my favorite book (also, I think human names for pets are funny). He turned nine on August 25 but still has kitten energy. He is a giant weirdo who enjoys embarrassing me by licking walls when I have guests over and sitting on things I’d rather he didn’t, such as my warm laptop keyboard, which has not yet produced any useable crossword fill.
Rapid-Fire Round:
Constructing or solving?
Constructing
Higher or lower word count themelesses?
Higher
Musicals or plays?
Musicals
Board games or bar trivia?
Board games
Favorite clue you’ve written?
[Kickstarter program?] – KARATE LESSONS
Memorable clue you’ve come across when solving?
I think about [someone who’s unmatched on bumble?] for OAF from this great Kelsey/Erik collab all the time.
Any upcoming projects?
I occasionally post pop-culture-heavy puzzles to my blog, Poppy Puzzles!
Go-to emoji?
👀 (I love to be intrigued. I love to be going “ooh.”)
Three words your friends would use to describe you.
Obsessive, adventurous, sincere
A Midwest interview wouldn’t be complete without talking about the weather. Favorite season?
Fall!
👀👀👀👀👀👀👀👀👀👀👀👀👀👀👀👀👀👀👀👀👀
This interview has been edited and condensed.
Jess Rucks is a crossword constructor and children’s therapist. She loves combining her curiosity about people with her passion for crosswords in DCL’s Constructor Spotlight.