You’ve been there. You are staring at a grid, three letters deep into a five-letter word, and the clue just says "Pretty, pretty please." It feels like a layup. You think of every time you’ve begged for a favor or watched a cartoon character widen their eyes to the size of dinner plates. But in the world of crosswords—especially if you’re tackling the New York Times or the LA Times—what seems like a simple plea is usually a clever bit of linguistic misdirection.
The most common answer? BEG.
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But wait. It isn't always that simple. Depending on the day of the week or the deviousness of the constructor, that "pretty pretty please" crossword clue could be angling for something entirely different. It might be asking for a synonym of "sue," or perhaps it’s looking for the word PRAY. If the clue has a question mark at the end, all bets are off.
The Anatomy of the Beg: Why Construction Matters
Crossword constructors like Will Shortz or Joel Fagliano don't just throw words at a wall. They look for "resonance." When you see "pretty pretty please" as a clue, the repetition is the key. In English, we repeat words for emphasis, a process linguists call reduplication. In a crossword context, this often signals that the answer itself needs to be punchy, short, and evocative of an action.
BEG fits this perfectly. It’s a three-letter powerhouse.
However, you have to look at the grid. If you’re filling out a Friday puzzle, "Pretty, pretty please" might not be a verb at all. It could be an adjective phrase leading you toward SUGAR. Why? Because of the common idiom "Sugar on top?" which is the ultimate "pretty please" additive. This is where people get stuck. They get "tunnel vision" on the act of asking and forget the cultural baggage attached to the phrase.
Honestly, the hardest part of solving these is letting go of your first instinct. If BEG doesn't fit the "downs," stop trying to make it happen. It’s not going to happen.
Decoding the Developer’s Intent
Constructors use these "cute" clues to mask common words. Let’s be real: words like BEG, ASK, and PRAY are in almost every puzzle because they are "vowel-heavy" or contain high-frequency consonants. They are the glue that holds the harder, 15-letter entries together. To keep the puzzle from being boring, the creator has to dress up these "glue words" in fancy costumes.
"Pretty, pretty please" is just BEG wearing a tuxedo.
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Sometimes, the clue is even more literal. I’ve seen versions where the answer was ENTREAT or BESEECH. Those usually appear in Sunday puzzles where the word count is higher and the space for longer strings is available. If you see "Pretty, pretty please" and you have seven boxes, don't panic. Just start thinking of the more formal, almost Shakespearean ways to ask for something.
- Check the tense. Is it "pleased" or "pleading"?
- Look for the "crosses." If you have a 'G' at the end, it’s almost certainly BEG.
- Count the repetitions. Three "pleases" might mean a different word length than two.
The "Sugar" Variation and Other Outliers
One of the more frustrating instances of this clue appeared a few years back where the answer was CHERRY.
Wait, what?
"With a cherry on top."
It’s an indirect clue. These are the ones that make people throw their tablets across the room. The clue isn't a definition; it’s a completion of a social script. You say "Pretty please," the other person says "With a cherry on top?" It’s a bit of a stretch, but in the world of high-level puzzling, it’s fair game.
Then there is the I’M BEGGING YOU possibility. In larger grids, the entire phrase "pretty pretty please" acts as a quote. When a clue is in quotes, the answer is often a direct spoken-word equivalent. So, "Pretty, pretty please" (in quotes) = "DO I HAVE TO?" or "PLEASE?!"
Why We Get Stuck on Simple Clues
There’s a psychological phenomenon at play here. When we see a repetitive, "childlike" phrase like "pretty pretty please," our brains switch to a simpler mode of processing. We think of kids, ice cream, or puppies. We stop thinking about the mechanics of the English language.
Crossword experts like Deb Amlen have often noted that the "easiest" clues are frequently the ones with the highest failure rates for experienced solvers. Why? Because we overthink them. We assume there must be a trick. Sometimes, "pretty please" just means BEG.
But on a Saturday? On a Saturday, it’s never just BEG.
On a Saturday, the constructor might be looking for SUE. Not the name, but the legal action. To "sue" for peace is to "plead" for it. It’s a reach, sure, but that’s the beauty of the game. It forces your brain to bridge the gap between a toddler asking for a cookie and a diplomat asking for a ceasefire.
Strategy for Your Next Grid
Next time you see this clue, don't just ink in BEG. Take a breath. Look at the surrounding area. If the word above it is a heavy hitter like ZIGGURAT or QUETZAL, you know you're in a high-difficulty zone.
If you're stuck, try this:
- Say the clue out loud. Often, the inflection you use will trigger the right synonym.
- Look for a question mark. If it's "Pretty, pretty please?", the answer is likely a pun or a non-literal association like CHERRY or SUGAR.
- Check the word length immediately. If it's four letters, try PRAY. If it's three, it's BEG. If it's six, maybe ADJURE.
The "pretty pretty please" crossword clue is a classic for a reason. It’s versatile. It can be a filler or a focal point. It’s the kind of clue that reminds us that English is a weird, repetitive, and deeply contextual language.
Actionable Solving Tips
Stop viewing the clue in a vacuum. Crosswords are a conversation between you and the constructor. If they’ve been using a lot of puns throughout the puzzle, the "pretty please" clue is probably a pun too. If the rest of the puzzle is straightforward and "Monday-easy," just go with the most obvious verb.
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Your Next Steps:
- Audit your "downs": Before committing to BEG, ensure the 'B' and the 'G' don't ruin a more obvious long-form answer.
- Keep a mental list of "fillers": Start recognizing that BEG, ASK, and SUE are the triple-threat of three-letter pleading clues.
- Practice with different outlets: The Wall Street Journal puzzles handle this clue very differently than the Universal Crossword. Learn the "personality" of the puzzle you're solving.
Crosswords are won in the margins. It’s the three-letter words that provide the scaffolding for the 15-letter masterpieces. Master the "pretty pretty please" clues of the world, and you'll find the rest of the grid starts to fall into place much faster.