Staring at those blank white squares is a special kind of torture. You’ve got the "across" answers mostly filled in, but that one stubborn down clue is mocking you. It says "win over." Five letters. Or maybe four. Or six. You start cycling through every possible synonym in your head. Is it "persuade"? No, too long. "Charm"? Maybe. But it doesn't fit the "R" you got from that weird 1950s actress clue.
Crossword puzzles are basically a battle of wits between you and an editor like Will Shortz or Patti Varol. They love words with double meanings. "Win over" is one of those frustratingly flexible phrases. It can mean to defeat someone in a game, or it can mean to convince someone to join your side. Honestly, that’s where most people trip up. They stick to one definition and refuse to let go.
The "win over" crossword clue is a classic "chameleon" clue. It changes colors based on the grid’s needs. If you're stuck on a New York Times Monday, it’s probably something simple. If it's a Saturday LA Times puzzle, prepare for some linguistic gymnastics. Let’s break down why this specific clue is such a headache and how to actually solve it.
The Most Likely Answers for Win Over
When you see "win over" in a puzzle, your brain should immediately jump to ENDEAR. This is the heavyweight champion of "win over" answers. If you endear yourself to someone, you’ve won them over. It shows up constantly because those vowels (E, A, E) are gold for crossword constructors trying to bridge difficult sections of the map.
But wait. What if it’s four letters? Then you’re likely looking at COAX or SWAY. To sway someone is to win them over to your point of view. It’s elegant, short, and fits into tight corners. If the vibe of the clue feels a bit more aggressive, like winning someone over in a competition, you might be looking at BEAT or BEST. Though, let’s be real, "best" as a verb is a bit "old-timey" for most casual conversations, yet it’s a crossword staple.
Another big one? CONVINCE. This is the literalist’s choice. If the grid allows for eight letters, this is a high-probability candidate. Then there is ENTICE. This carries a bit more of a "temptation" flavor. You aren't just winning them over; you’re dangling a carrot. Crossword solvers often miss this because they think too much about logic and not enough about seduction.
Why Crossword Constructors Love This Clue
Constructors are basically architects who have to build a house using only specific blocks. They love "win over" because it’s a "transitive verb phrase." That sounds fancy, but it just means it needs an object. This gives them flexibility. They can use it to lead you toward words that end in "ED" or "ING" if they need to fill a specific suffix.
Take the word ADOPT. Sometimes "win over" is used in the context of winning someone over to a cause, leading them to adopt a new stance. Or consider GET. It’s so simple it’s almost offensive. "I finally got him to see my way." In a three-letter slot, "GET" is a nightmare because it’s so vague. You’re looking for something complex, and the answer is just three letters long.
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The New York Times crossword often uses "Win over" to lead to CARRY. Think about an election. A candidate wins over a state; they "carry" that state. If you aren't thinking about politics, you'll never find that answer. You'll be sitting there wondering how "carrying" a box has anything to do with winning. Context is everything.
Nuance and the Art of the Near-Synonym
Sometimes the clue isn't "win over" but something slightly shifted, like "Won over." That "ED" at the end is a massive hint. Your answer almost certainly ends in "ED." CAJOLED is a favorite here. It’s a fun word to say, and it’s a fun word to type. It implies a bit of flattery or light teasing to get your way.
If the answer is WOOED, you’re looking at a three or four-letter situation. "Woo" is very old-school. It’s what people did before dating apps. But in the world of crosswords, people are still "wooing" and "suing" and "averring" all over the place. You have to step out of 2026 and into a world where people use fountain pens and wear hats.
Then there is PREVAIL. This is a bit of a stretch for "win over" in a social sense, but in a competitive sense, it’s perfect. If you prevail over an opponent, you’ve won. However, "prevail" usually requires the word "over" to follow it, whereas "win over" is the clue itself. This is a subtle distinction that seasoned solvers use to rule out certain words. If the clue is "Win over," and the answer is PREVAIL, the constructor is being a bit cheeky by using part of the answer's natural phrasing in the clue itself.
A List of Potential Candidates by Letter Count
- 3 Letters: GET, WOO
- 4 Letters: SWAY, COAX, BEAT, BEST
- 5 Letters: ADOPT, CARRY, ELECT
- 6 Letters: ENDEAR, INDUCE, ENTICE
- 7 Letters: PREVAIL, CONVERT, ATTRACT
- 8 Letters: CONVINCE, PERSUADE
The Psychology of the "Aha!" Moment
There’s a reason people do the Sunday crossword religiously. It’s the hit of dopamine you get when a word like PROSELYTIZE (if you’re dealing with a massive grid) finally clicks. But "win over" usually points to something more mundane. The frustration comes when you’re overthinking. You’re looking for a PhD-level word when the constructor just wanted EARN.
If you earn someone’s trust, you’ve won them over. It’s a clean, four-letter word that fits into almost any corner. Most people miss "EARN" because it feels too simple. We want the puzzle to be hard, so we ignore the obvious.
If you’re stuck, look at the crossing words. If the second letter of your "win over" answer is an "A," and the fourth is an "Y," it’s SWAY. Don't fight it. Don't try to make "STAY" work because you think the clue is about a legal injunction. Crosswords are about trust. You have to trust that the constructor isn't lying to you, even if they are being annoying.
Strategic Tips for Your Next Puzzle
Stop looking at the clue in isolation. If "win over" isn't making sense, ignore it. Fill in the letters around it. Crosswords are a game of intersection. If you get the "D" in ENDEAR from a different clue, the whole thing might just fall into place.
Also, pay attention to the punctuation. If "Win over?" has a question mark, it means the constructor is using a pun or a non-literal definition. Maybe it’s not about winning a person over, but about "winning" in a very specific, weird context—like a pun on "over" meaning "above." For instance, someone who "wins over" a high-jump bar might just be a LEAPER. That’s the kind of stuff that makes people want to throw their tablet across the room.
Check for tense. If the clue is "Wins over," the answer must end in an "S," like SWAYS or COAXES. If it's "Winning over," look for that "ING" ending, like 诱导 (just kidding, that's Chinese, I mean something like COAXING). Match the part of speech and the tense, and you’ll eliminate 70% of the wrong guesses instantly.
Real-World Examples from Major Puzzles
In a recent New York Times puzzle, "Win over" was the clue for ENDEAR. In a Wall Street Journal puzzle from a few months back, the same clue led to SWAY. The LA Times once used it for GET TO, which is a two-word answer that drives people crazy because they expect a single word.
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If you see "Win over" in a themed puzzle, look at the theme title. If the theme is "Political Science," the answer is almost certainly CONVERT or CARRY. If the theme is "Romance," you're looking at WOO or CHARM. The theme is your North Star. Use it.
Moving Beyond the Clue
Look, solving crosswords is a skill that develops over years. You start recognizing the "repeat offenders"—words like ETUI, ALEE, and OREO that appear because their letter combinations are convenient. "Win over" is a "tier-two" repeat offender. It’s not in every puzzle, but it’s in enough of them that you should have a mental list of candidates ready to go.
Don't be afraid to use a digital solver if you're truly stuck. There’s no "crossword police" coming to your house. Sites like Crossword Tracker or Rex Parker’s blog are great for seeing how these clues have been used in the past. It’s not cheating; it’s research. You’re building your vocabulary for the next battle.
When you finally fill in that last letter, take a second to look at the word. ENDEAR. It’s a nice word. It means you’ve made someone like you. In a world that feels increasingly divided, maybe we all need to spend a little more time trying to "win over" the people around us. Or at least, "win over" the Saturday puzzle before the coffee gets cold.
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Actionable Next Steps for Solvers:
- Maintain a "Cheat Sheet": Keep a small digital note of common synonyms for frequent clues like "win over," "area," and "edge."
- Verify the Tense: Always double-check if the clue is "win," "wins," "winning," or "won" before committed to an answer.
- Count the Squares: Don't even start brainstorming until you know the exact letter count; it narrows your options from hundreds to about five.
- Work the Crosses: If the synonym doesn't jump out in 10 seconds, move to the intersecting clues. The "Aha!" moment usually comes from a different direction.
- Study the Constructor: If you know you're playing a David Steinberg puzzle, expect more modern slang; if it's an older syndicated puzzle, think more formally.
- Embrace the Pun: If there's a question mark at the end of "Win over?", stop thinking about persuasion and start thinking about physical movement or wordplay.