"So why are you still single?"
It arrives somewhere in the first week, usually when things are going well, and it stops a lot of men dead. It sounds like a compliment and a challenge at the same time, and there is no obvious right answer to it.
Most men then do the worst available thing, which is take it seriously.
What she is actually checking
She is not running a background check. She is checking your temperature.
Every woman on an app has talked to a man who answered this question with a monologue. Sometimes it is bitterness about women. Sometimes it is a long account of a relationship that ended two years ago and is clearly not finished. Sometimes it is a list of his own flaws, offered up like evidence.
All three tell her the same thing: this is going to be heavy, and she will end up managing it.
So the question is really "is there anything unpleasant waiting behind this conversation?" Your answer is mostly tone. Light and unbothered passes. Anything with weight on it does not.
The four answers that cost you
The confession. "Honestly I've had a rough couple of years and my confidence took a hit." It is true and it is brave and it is far too early. She has not met you. She cannot hold that yet.
The bitterness, even a small amount of it. "Dating apps are a nightmare these days." "Most women on here don't want anything real." She is a woman on here. You just told her what you think of her.
The ex tour. Any answer that includes what your last girlfriend did, how long it lasted, or how it ended. She asked one question and got a file.
The self roast. "Ha, good question, probably my terrible personality." Jokes at your own expense are fine in small doses, but not as an answer to this one. It reads as a man fishing to be told otherwise, and she will feel obliged to reassure you.
The shape that works
Short. Light. No defence. Then move.
The whole answer is one or two sentences, delivered like it is not a big question, because it is not.
"Was in a long one, it ended, took a bit of time out, and now I'm here being interrogated by a stranger."
"Busy couple of years and I wasn't dating properly. I am now."
"No good story, I'm afraid. I just haven't met the right person yet and I'd rather be single than nearly right."
None of those explain anything. That is the point. An explanation implies the situation needs one.
Three honest positions, said lightly
If you came out of something long, say it in a clause and keep walking. "Long relationship, ended a while back, and I took my time before getting back into this." One sentence is enough. If she wants more she will ask, and then you answer that question rather than volunteering it.
If you have been dating and nothing stuck, own it with no apology. "I've met some good people, none of them were quite it. I'd rather keep looking than settle in somewhere comfortable." Confident, not defensive, and it quietly says you have standards.
If you genuinely have not been trying, just say so. "Work got busy and I let it slide for a while. Sorting that out now." Men are terrified of this answer and women barely blink at it.
Do not audit yourself out loud
The instinct under this question is to be honest in a way that helps her decide. So you tell her about the shyness, or the divorce, or the year you barely left the house.
None of that is dishonest. It is just wildly out of order. Those things come out over a few dates, once she knows you, in a version where she can see you are fine now.
Answered in week one over text, the same material reads as a warning. Same facts, completely different meaning, purely because of when it arrives.
Send it back without mirroring
You can turn it around, but not as a bounce. Firing back "what about you?" with nothing attached is transparently a dodge.
Answer first, then ask, and make it playful rather than symmetrical. "That's my version. Now you, and I want the real answer, not the polite one."
You get the same information she was after, and it keeps the exchange even.
Then take it somewhere
This question is a good moment to make a plan, because it means she is curious about you rather than about your profile.
"Anyway, this is the sort of thing that goes better over a drink than over text. There's a bar near me I like. Thursday or Saturday?"
Answering well and then sitting there waiting is how a good exchange turns into a week of texting. The answer is not the win. What you do in the next message is.
When the answers keep landing heavy
If conversations tend to cool right around here, it is usually not the words you chose. It is the weight underneath them, which is close to impossible to hear in your own writing.
Someone reading your last few conversations will spot it fast. An hour on a call with a coach, going through what you actually sent, is the shortest route to knowing why a good exchange keeps flattening out at the same place.
Written by Matthew Stevens, Co-Founder & Head Coach. More than half a decade coaching men across the US and worldwide.
Everything here comes out of real coaching work: the approaches, dates, texts and profiles we go through with the men we coach.
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