New York Times, Thursday, May 29, 2014

In the past nine months I've worked as Will Shortz's assistant. One of the job's perks is getting to discuss theme ideas with Will, often over lunch. Will sanctioned this puzzle — whose theme is a pun on a symbol (#), as opposed to a word — in February.

I still construct by hand, so this 72-word grid took many late nights to fill cleanly. So many nights, actually, that I may finally be convinced to construct using software. It's a long time coming: when I learned in January that Bernice Gordon, the Times' only centenarian cruciverbalist, uses software, my graph paper and pencil technique seemed not so much retro as retrograde.

Ultimately, though, I'm happy with this puzzle's fill (with the exception of a couple unfortunate partial phrases). The only word that gave Will real pause was SHTUP, which he and I debated at length. I suggested that if Rachel Maddow can say it on msnbc, and my dad can say it at Passover, it had evolved beyond its crude Yiddish origins (from the German stopfen "to stuff"). Here's hoping most solvers agree.

I so regret leaving Will next month, but I'm giddy to start graduate school in English and film studies in the fall. It's been a total joy working with him — from fact-checking to cluing to debating the vulgarity of SHTUP. #dreamjob #thanksWill

Thursday brings trickery at the NYT, and Anna nicely plays on the pound sign. #1 doesn't mean "number one" at all, rather it describes the puzzle's first #, a TIC TAC TOE BOARD. Neat idea. TWITTER HASHTAG is a great entry as well, and POUND SIGN is what will come to mind first for most. SPACE MARK was a little bit of a head-scratcher, but it is definitely used by editors for that purpose. I'd almost prefer to see just three themers today (without SPACE MARK), but then again, that might have made the puzzle feel too thin.

I really enjoyed meeting Anna at the ACPT and a couple of us got to chatting about co-constructing. I find it so fun to work with other people. She and I exchanged some emails afterward, and I suggested trying to make the grid look like a pound sign as an added bonus. Not an easy task, and the end results looked sort of pound sign-ish. (Emphasis on the "ish".)

In the end, Anna chose to go a different direction, and I like that it gives the solver a more crunchy, themeless-vibed puzzle, a 72-worder. Quite impressive that she managed to pack in not just two long downs like many themed puzzles. Not just four, either. Or six. But eight? EIGHT? Not sure I'd attempt that myself, especially considering they're done in adjacent pairs. And dang, GAY ANTHEM next to WHERE ITS AT surely is the definition of WHERE ITS AT. With so much long fill, you'd expect much of it to be blah words full of E's and S's, but PANT SUITS / BUBBLE WRAP / NEIL SIMON makes for some EPICNESS. Very well done!

Such constraints will almost always come with some compromises, though. And we do see some subpar entries, mostly running through those long down pairs. TREN. AH SO. TELEO. ISAO. NEUE. Some constructors choose the safe path, little quality fill and little glue entries, Anna choose to go big or go home.

Speaking of which... SHTUP. Take that, Gray Lady! Not often that I giggle nervously due to a five-letter entry. Curious to see how much mail Will's going to get for that one. Not adding that one to my word list quite yet, but I sure got a hoot out of uncovering it.

Overall, a fun experience. I also appreciated how this puzzle has a modern feel to it, what with OPRAH's new Starbucks beverage and a reference to ESPN buying Nate Silver's 538 site. During our chats, I found out that Anna was still using grid paper / Excel to construct. If this is what she can do by hand, I can't wait to see what she can produce with the assistance of software. Looking forward to more!

ADDED NOTE: Great interview with Anna!