Published On: Sun, Dec 3rd, 2023

A conversation with Dec. 3 crossword creator Robyn Weintraub

A conversation with Dec. 3 crossword creator Robyn Weintraub
A conversation with Dec. 3 crossword creator Robyn Weintraub


We recently spoke with Robyn Weintraub, who is among the crossword constructors filling in for Evan Birnholz until his return from paternity leave in January. The solution to her Sunday puzzle is posted below. Scroll down for our discussion, which has been edited for length and clarity.

Q: Welcome! Introduce yourself!

A: Hi! My name is Robyn Weintraub, and I live in Westchester County, New York. My puzzles appear regularly in the New York Times, the New Yorker and People magazine.

Q: How did you first get into crossword construction?

A: My mother was a huge crossword solver; she even attended various tournaments over the years. But I was a Games magazine/Scrabble/Boggle kid and largely ignored the crossword. I didn’t begin solving regularly until just before my 40th birthday, but it was a quick transition from solving to constructing.

Q: Which part of the process is the most challenging?

A: Writing the first draft of the clues is the part I dread the most. But my process was inspired by author Anne Lamott and what she terms “s—ty first drafts.” I write a bunch of garbage just to get something on the page and then do many rounds of edits.

Q: Do you have a favorite clue you’ve written, whether in this puzzle or a different one, that immediately comes to mind?

Here are a few off the top of my head:

[Game you can’t stand to win?] MUSICAL CHAIRS

[Hamburger or Frankfurter topping?] ROBE

[Exchange rings?] PLAY PHONE TAG

[Gift your friends are guaranteed to flip over?] SNOW GLOBE

Q: You’re well-known among crossword solvers for building fun themeless crosswords with smooth grids. What drew you to themeless puzzles?

A: I started, like most constructors, making themed puzzles. It was a slow process, and months would go by before I had a solid theme ready to go. I much prefer constructing grids to the process of coming up with themes. One day it occurred to me that if I switched to themeless puzzles, I could just skip the theme brainstorming and go directly to constructing! It seems obvious now, but back then it felt like a really big leap for a novice constructor.

Q: When you write a puzzle, do you have a particular set of interests that you aim to include in the answers or clues?

A: In my puzzles you’re likely to see references to musical theater, kid-friendly characters, Shakespeare, food/cooking and Gen X trivia. What you will not find — at least when I can help it — are any references to sports.

Q: There have been a few times where you’ve constructed a themeless puzzle for a special occasion and had to write more than one set of clues with different difficulty levels. How do you approach this sort of multi-difficulty project?

A: I assemble a spreadsheet with three columns for Easy, Medium and Hard and then just start brainstorming. Sometimes clues get shifted between columns as I edit.

I do have the distinct honor of making both difficult(ish) themeless puzzles for the New York Times — typically my puzzles there run on Fridays, but I have had a few Saturdays as well — and a regular gig at the New Yorker where I make “beginner-friendly” themeless puzzles.

I’d burn out pretty quickly if all my puzzles fell into the same difficulty level. I enjoy writing the clues for both hard and easy themelesses, but it really is a different process. For the hard ones, it’s much more about finding clever misdirection, which can be a thrill, but also mentally exhausting. For the easy ones, I try to include a fun fact or trivia in the clues to keep them from feeling one-dimensional.

Q: Are there other puzzle activities or projects that you’d like to promote?

A: I have a book of hard midi (9×9) puzzles, which is part of a series entitled Sit and Solve (yes, it’s that “Sit”; the cover art is shaped like a roll of toilet paper). It’s available at the website of your favorite book retailer. This summer the BBC did a podcast episode about me, recorded while I constructed a New York Times puzzle; I think solvers will find it interesting to hear how a constructor makes a puzzle from start to finish, including all the joys and frustrations of the creative process.


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