It happens to the best of us. You’re sitting there with your coffee, the New York Times app open, and you hit a wall. One specific clue stops you cold: "Like someone you shouldn't trust." You start counting the squares. Four? Five? Six?
Suddenly, your brain goes into overdrive trying to categorize every shady person you’ve ever met. Is it "liar"? No, too simple. "Shifty"? Maybe. "Sleazy"? Possibly, but the NYT usually keeps things a bit more sophisticated than that, even on a Saturday. Honestly, the beauty of a Will Shortz-edited puzzle (or the newer era under Joel Fagliano) is that the answer is rarely the first thing you think of. It’s always a bit sideways.
The Psychology of the NYT Wordplay
Crossword constructors love "like someone you shouldn't trust" because it’s a goldmine for adjectives. They aren't just looking for a synonym; they’re looking for a vibe. If you’re staring at a five-letter space, the answer is almost certainly SHADY.
Why? Because it’s evocative.
It fits the "Friday/Saturday" difficulty curve where the clue is technically accurate but intentionally vague. If the answer is SLY, it’s usually a Monday or Tuesday. If it’s FISHTY, well, that’s just a typo in your head—you’re thinking of FISHY.
When the Answer is SHADY
In the world of the New York Times Crossword, "shady" is the king of distrust. It’s been used dozens of times over the last decade. But here’s the thing: the clue often shifts slightly. Sometimes it’s "Like a suspicious character" or "Hardly reliable."
Think about the last time you actually used that word in real life. You probably weren't talking about a tree. You were talking about that guy on Facebook Marketplace trying to sell a "slightly used" parachute. That’s exactly the energy the NYT editors are tapping into.
Other Common Answers You’ll See
If SHADY isn't fitting the crosses, you’ve got to pivot. The English language is surprisingly rich with ways to describe people we don't like.
- SLICK: This is a favorite for four-letter slots. It implies someone who is a bit too smooth, a bit too practiced. A "slick" operator is someone you shouldn't trust because they’ve already sold you the Brooklyn Bridge before you’ve finished your latte.
- DODGY: This one pops up more often when the constructor has a bit of a British flair or is looking to fill a five-letter gap with a 'Y' at the end.
- OILY: Gross, right? But it’s a classic crossword staple. It describes that sycophantic, untrustworthy vibe that makes your skin crawl.
- TWO-FACED: If you’re looking at a long, hyphenated mess in a Sunday puzzle, this is your winner. It’s the ultimate description for a betrayer.
Why These Clues Trend on Google
You aren't alone in searching for this. Thousands of people hit Google every morning because they’re stuck on the same word. The NYT Crossword is a communal experience. When a clue like "like someone you shouldn't trust" appears, it creates a micro-moment of collective frustration.
The search intent here is simple: you want the answer, but you also want to know why that’s the answer.
Crosswords are basically a battle of wits between you and the constructor. When the constructor uses a phrase like "Like someone you shouldn't trust," they are purposely using a "non-specific descriptor." This is a tactic to prevent you from getting the "gimme" answers. They want you to work for it. They want you to look at the intersecting words—the "crosses"—to narrow it down.
Understanding the "Crosswordese" Factor
There’s a concept called Crosswordese. These are words that show up in puzzles way more often than they do in real life. Think of words like "ERIE," "ALEE," or "ETUI."
While "shady" or "sly" aren't strictly crosswordese, the way they are clued is. The NYT has a specific "voice." It’s literate, slightly smug, and deeply obsessed with puns.
If the clue has a question mark at the end—"Like someone you shouldn't trust?"—everything changes. The question mark is a universal signal in crosswords that a pun is involved. In that case, the answer might not be an adjective for a person at all. It could be something like UNSTEADY (someone you literally shouldn't trust to hold something) or something even more lateral.
Real Talk: How to Solve it Without Googling
I know, you're already here, so you've kind of "cheated" (no judgment, we all do it). But if you want to get better at the NYT puzzle, you have to learn to anticipate the "Trust" clues.
- Check the vowel count. If you have an 'A' and a 'Y', it’s SHADY.
- Look for the 'I'. If there's an 'I' in the middle, it’s likely OILY or SLICK.
- Read the tone. Is the puzzle a Monday or a Saturday? Monday wants BAD. Saturday wants DISTRUSTFUL.
The New York Times doesn't just want to test your vocabulary. They want to test your ability to think like a person who enjoys being slightly annoyed by wordplay.
The Evolution of Trust-Based Clues
If you look back at puzzles from the 1990s, the clues were much more straightforward. "Untrustworthy" might just lead to "FALSE." But the modern era of the NYT Crossword, especially under the influence of indie constructors who have moved into the mainstream, prefers "personality" clues.
They want the puzzle to feel like a conversation. "Like someone you shouldn't trust" sounds like something a friend would say while whispering in a bar. It’s evocative. It creates a mental image.
That’s why the answer is so often SHADY. It’s a word that carries weight. It’s not just about lying; it’s about a lack of transparency. In an era of misinformation and digital "shadiness," the clue feels more relevant than ever.
Does the "NYT" Part Matter?
Yes. Each publication has a different "word list." The Los Angeles Times crossword is generally seen as more straightforward. The Wall Street Journal loves a good theme. The New Yorker is notoriously difficult on Mondays and gets easier throughout the week (the opposite of the NYT).
When you see "like someone you shouldn't trust" in an NYT puzzle, you have to prepare for the specific brand of cleverness that the Gray Lady is known for. They love words that function as both metaphors and literal descriptions.
Moving Beyond the Clue
So you’ve filled in the squares. You’ve realized it was SHADY or SLY or CREEPY. What now?
The best way to stop being stumped by these is to start noticing the patterns in how the NYT handles human character traits. They love adjectives ending in -Y. They love words that can be used for both people and physical objects (like "shady" trees or "slick" roads).
Next time you hit a "trust" clue, don't just think about villains. Think about the adjectives you'd use to describe a politician you don't like or a car salesman who seems a bit too eager. Usually, the answer is hiding right there in your everyday frustrations.
Practical Steps for Your Next Puzzle
- Scan for the "Question Mark": If it's there, think of a pun involving "trust" (like a bank trust or a physical trust).
- Fill the Crosses First: Never try to guess "Like someone you shouldn't trust" in a vacuum. You need at least two letters to be sure.
- Think in Synonyms of "Suspicious": If SHADY doesn't work, try FISHY, DODGY, or SUS (though the NYT only recently started using "SUS" as modern slang).
- Keep a Mental List of 4 and 5 Letter Adjectives: Most trust-related clues fall into these lengths.
Crosswords are a game of pattern recognition. The more you see "Like someone you shouldn't trust," the faster your brain will leap to the correct answer. You'll stop seeing it as a hurdle and start seeing it as an old friend—or, at least, an old, untrustworthy acquaintance.