You're staring at the grid, the cursor is blinking, and the clue says "Pretty, pretty please." It’s five letters. Or maybe it’s four. You think it’s easy because you say it all the time, but the pretty pretty please NYT crossword clue is a classic example of how Will Shortz and his team of editors turn simple conversational English into a mental trap.
Crosswords aren't just about vocabulary. They’re about vibes.
👉 See also: How to Master I Fought the Law GTA 5 Without Losing Your Mind
When a clue uses a phrase like "pretty, pretty please," it’s signaling a specific register of speech. It's childish. It’s pleading. It’s something a toddler says when they want an extra cookie, or something a partner says when they’re trying to be playfully manipulative. In the world of the New York Times crossword, the answer almost always reflects that exact tone.
The Most Common Answers for Pretty Pretty Please
If you’re stuck right now, let’s get to the point. Most of the time, the answer is CHERRY. Why? Think about the phrase "Pretty please with a cherry on top." The crossword loves a "clue by association." It isn't asking for a synonym; it’s asking for the completion of a common idiom.
But it’s not always that simple. Depending on the day of the week—and we know the NYT gets progressively harder from Monday to Saturday—the answer could be BEG. Or even I BEG.
When the Answer is CHERRY
This usually shows up on Mondays or Tuesdays. It’s straightforward. The clue is acting as a "fill in the blank" without actually giving you the blank. If you see five letters and the cross-references (the "down" clues) involve fruit or desserts, you can bet your Sunday subscription it’s CHERRY.
When the Answer is BEG or I BEG
If the grid requires three or four letters, the editor is looking for the verb. "Pretty please" is an act of begging. Sometimes the clue is written as "Pretty please?" with a question mark. In "crosswordese," that question mark is a flashing neon sign that says, "I’m being punny or literal in a way you don't expect."
The Outliers: DO or AM
Occasionally, the clue is part of a larger theme. If the answer is DO, it might be part of a phrase like "DO TELL." If it's AM, it might be a weird grammatical play. But honestly? These are rare. Stick to the "pleading" synonyms or the "cherry" idiom first.
Understanding the "Vibe" of the NYT Clue
Crossword construction is an art form. People like Joel Fagliano or Sam Ezersky don't just pick words out of a hat. They look for "collocations"—words that naturally sit next to each other in the English language.
👉 See also: Frame Rate for Xbox One: What Most People Get Wrong
"Pretty please" is a high-frequency collocation.
When you see a clue repeated in quotes, like "Pretty, pretty please!", it almost always means the answer is a direct quote or a synonym for the act of saying that phrase. If there are no quotes, it might be a description of the word itself. This is a subtle distinction that separates the casual solvers from the people who finish the Saturday puzzle in ten minutes while drinking lukewarm espresso.
Why the NYT Crossword Uses Redundancy
Why "pretty, pretty" and not just "pretty"?
The repetition indicates emphasis and a specific "cuteness" factor. This narrows the field of possible answers. You wouldn't answer PRAY to "pretty, pretty please" because "pray" is too formal, even though it technically means the same thing in an archaic sense. You need something that matches the "sugar-coated" energy of the clue.
📖 Related: Playing AI Minecraft: How to Get Started with Intelligent NPCs and Agents
- SUGAR (Occasionally used if the clue refers to the "on top" part).
- PLEASE (Rarely, because the word is in the clue, but it happens in "meta" puzzles).
- TEASE (If the clue is a rhyming play).
The Psychology of the Solve
There’s a specific frustration when you know the answer is right in front of you. You’ve said these words a thousand times. But the pretty pretty please NYT crossword clue works because it forces you to deconstruct your own speech patterns.
Most people overthink it. They start looking for Latin roots or obscure 18th-century poets. Don't do that. The NYT has shifted in recent years to be more "New York" and more "Modern." It reflects how we talk now. It reflects pop culture. If the clue sounds like something a character in a sitcom would say, the answer is probably a sitcom-level word.
Real Examples from Past Puzzles
Let's look at some actual data from the NYT archives. In a 2018 puzzle, the clue "Pretty please?" led directly to I BEG YOU. In a 2021 Wednesday puzzle, "Pretty please with a cherry on top" was shortened significantly, and the answer was simply TREAT.
You see the pattern? The length of the entry is your best friend.
- 3 Letters: BEG
- 4 Letters: I BEG
- 5 Letters: CHERRY
- 6 Letters: BEGGED
How to Get Better at These Clues
If you want to stop getting stumped by the pretty pretty please NYT crossword variants, you have to start thinking in "blocks."
Look at the surrounding letters. If you have a _ H _ _ R _, it’s CHERRY. If you have a _ E _, it’s BEG. Don't try to solve the clue in a vacuum. The crossword is a grid for a reason; the words support each other. If you’re struggling with the "across," solve all the "downs" that intersect it.
Honestly, the "pretty please" clue is often a "gimme." It's designed to give you a foothold in a difficult section of the puzzle. If you’re seeing it on a Friday or Saturday, though, watch out. It might be a trick. It might be referring to someone named "Pretty" or a very specific, obscure piece of slang.
Actionable Tips for Your Next Puzzle
Stop treats clues as definitions. Treat them as riddles.
- Check the punctuation. A question mark means a pun. Quotes mean a spoken phrase. No punctuation means a direct definition.
- Say it out loud. Sometimes hearing the phrase "pretty, pretty please" helps you remember the next word that naturally follows it.
- Look for the "on top." If the clue implies a request, the answer is often the thing being requested or the manner of the request.
- Fill in the vowels. Most of the common answers for this clue (CHERRY, BEG, SUGAR) have very predictable vowel placements.
The New York Times crossword is a conversation between you and the constructor. They want you to solve it, but they want you to work for it. Next time you see "pretty, pretty please," don't panic. Just think about what you’d say if you really, really wanted that last slice of pizza. You’d beg. Or you’d promise a cherry on top.
Start with CHERRY or BEG. If those don't fit, look at the letters you've already filled in from the vertical clues. Usually, the answer is hiding in plain sight, disguised by how simple it actually is.
Get back into the grid and try those letters. Most of the time, your first instinct—the simplest one—is the one that will let you move on to the rest of the puzzle.