You’re staring at your phone or the folded back page of the Styles section, and there it is. Four letters. A cryptic hint. You think you have the rhythm of the puzzle down, but then Will Shortz or the current editing team throws a curveball that feels less like a clue and more like a personal attack. This is the "bold choice perhaps NYT" phenomenon. It’s that specific moment where a clue feels slightly off-center, maybe a bit too experimental, or relies on a pun so strained you can practically hear the grid groaning.
Crossword puzzles are basically a contract between the constructor and the solver. You provide the logic; they provide the witty framework. But when the New York Times crossword makes a "bold choice," it’s often a linguistic gamble.
Sometimes it’s a rebus—those annoying but brilliant squares where you have to cram an entire word like "HEART" or "DIAMOND" into a single box. Other times, it’s a bit of slang that feels like your uncle trying to use TikTok lingo. It’s polarizing. Honestly, it’s what keeps the community talking on forums like Wordplay or Rex Parker’s blog.
The Anatomy of a Bold Choice in the NYT Crossword
What makes a clue "bold"? In the world of elite puzzling, boldness usually involves breaking the "unwritten rules." For decades, the NYT was the gold standard of formal, slightly academic trivia. Then things changed. They started including brand names, modern slang, and pop culture references that your grandmother definitely wouldn't know.
Take the word "DARING." If the clue is "Bold choice, perhaps," and the answer is "DARING," it's a straightforward synonym. Boring. But the NYT doesn't stay in that lane. They might use "ERA" or "STANCE" or "REB" to signify something much more complex.
The shift toward "New Wave" puzzles means constructors like Kameron Austin Collins or Brooke Husic are pushing the boundaries of what belongs in a grid. They use stacks of 15-letter words that shouldn't fit together but somehow do. That’s a bold choice. It’s risky because if one crossing word is too obscure, the whole corner of the puzzle becomes "Natick"—a term coined by Rex Parker to describe a crossing of two obscure proper nouns that makes a square unguessable.
Why the NYT Crossword Editor Takes These Risks
Will Shortz has been at the helm since 1993, but the editorial staff, including people like Sam Ezersky and Wyna Liu (who also handles the viral "Connections" game), have a specific goal. They have to keep the puzzle relevant. If the crossword stayed stuck in the 1950s with clues about "ETUI" (a small needle case) or "ERNE" (a sea eagle), the readership would literally die off.
So, they go bold.
They include clues about Beyoncé’s latest album or niche internet acronyms. This creates a friction point. Older solvers get frustrated because they don't know who "SZA" is, while younger solvers get annoyed when the puzzle relies on 1940s cinema stars. The "bold choice" is the editorial attempt to bridge that gap, even if it results in a few angry emails to the Times' public editor.
When Boldness Backfires: The Controversy of Modern Grids
Not every experiment works. You’ve probably seen the Twitter threads. A clue that uses a "slang" term that was actually out of date three years ago makes the NYT look like it’s "trying too hard." Or worse, a "bold choice" in a theme can make a puzzle nearly impossible to solve without a revealers.
The NYT has faced actual backlash for certain entries. There have been instances where words with insensitive historical connotations made it past the desk because they were viewed through a "purely linguistic" lens. These aren't just bold choices; they're editorial lapses. The community is vocal about this. Sites like XWord Info track every single word used in the history of the puzzle, so there is nowhere to hide. If a constructor uses a "bold" entry that leans into a trope or a microaggression, the data shows it, and the solvers call it out.
The Evolution of the "Tricky" Thursday
Thursday is the traditional day for the NYT to make its most "bold choice" regarding mechanics. If you’re solving on a Thursday, you should basically throw the rulebook out the window.
- Mirror Symmetry: Sometimes the grid is a literal mirror image.
- Themed Shapes: The black squares might form a picture of a bird or a skyscraper.
- Outside the Box: Some clues require you to literally write letters outside the grid.
These aren't just puzzles; they’re architectural feats. But for a casual solver looking for a quick hit of dopamine on their lunch break, these bold choices can be infuriating. You're not just testing your vocabulary; you're trying to read the constructor's mind.
How to Handle a Bold Choice Perhaps NYT Throws Your Way
If you’re stuck on a clue that feels like a "bold choice," you need to shift your perspective. Stop looking for synonyms. Start looking for puns. The NYT loves "question mark clues." If a clue ends in a question mark, like "Green house?," the answer isn't "BUNGALOW." It’s "IGLOO" (because it’s made of "frozen" water, and sometimes they get... okay, maybe "ECOHOME" is a better example).
Wait, no. Let's look at a real one. "Lead singer?" with a question mark often refers to a "CANTOR" or even "PENCIL" (because of the lead). That is the quintessential bold choice. It's a pun that plays on the literal versus the figurative.
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- Check the crossings. If the "bold" word is weird, the words crossing it are usually very solid. This is "fair" construction.
- Say the clue out loud. Sometimes the sound of the words reveals a pun you can't see on the screen.
- Think about the day of the week. A bold choice on a Monday is usually just a slightly clever pun. A bold choice on a Saturday is meant to end your winning streak.
The Cultural Impact of the NYT Crossword’s Boldness
We live in an era of "Connections" and "Wordle," but the Crossword remains the prestigious big brother. Because it’s the most famous puzzle in the world, its "bold choices" actually influence the English language. When a new word enters the NYT crossword, it’s a sign it has "arrived" in the cultural lexicon.
Whether it’s "ADULTING" or "BIPOC" or "CHILLAX," these entries validate modern usage. But it’s a double-edged sword. The "bold choice" to include these words often sparks a debate about what constitutes "real" English. It’s a fascinating look at how we communicate. The grid is a 15x15 snapshot of what we value, what we remember, and what we’re currently obsessed with.
Actionable Steps for Mastering the NYT Style
If you want to stop being tripped up by these bold editorial decisions, you have to train like an athlete. Seriously.
- Study the "Shortz Era" vocabulary. There are certain "glue" words (like OREO, ALOE, and ARIA) that appear constantly to help the bold choices fit into the grid. Learn them.
- Follow the constructors. Search for names like David Kwong or Elizabeth Gorski. They each have a "voice." Once you understand a constructor's style, their bold choices become predictable.
- Use a solver's app for practice, but don't rely on it. Apps like "Crossword Tracker" can help you see how a specific clue has been used in the past. If "Bold choice, perhaps" has appeared before, it’s likely a play on the word "FONT" (like Bold or Italic).
- Read the Wordplay blog daily. The official NYT crossword blog explains the logic behind the "bold" themes every single day. It’s the best way to learn why a certain choice was made.
The next time you encounter a "bold choice perhaps NYT" style clue, don't get frustrated. See it as a challenge to your cognitive flexibility. The puzzle isn't just a test of what you know; it's a test of how you think. If you can anticipate the "boldness," you're not just a solver—you're a master of the game.
To truly improve, start by going back through the archives of Monday puzzles from five years ago. Compare them to Mondays from this year. You’ll see the shift in real-time. The clues are punchier, the references are fresher, and the "bold choices" are becoming the new standard. Embrace the weirdness of the grid, and you’ll find that the most frustrating clues often lead to the most satisfying "Aha!" moments.