Ask fewer questions than feels natural, and make each one specific enough that she could only be answering you. The good ones come off something she put on her page, take a line to answer, and ask about a choice rather than a fact. Then you answer your own question, so she is talking with a man instead of filling in a form.
Why most questions get a one-word answer
Look at what you usually send. What do you do. Where are you from. How was your weekend. Any plans for the summer.
Every one of those has a correct answer that takes four words, and once she has given it the ball is back with you and nothing has happened. You have learned a fact you could have guessed and she has learned nothing at all about what talking to you is like.
There is a second cost, and it is the bigger one. A run of questions puts her in charge of the whole exchange. She answers, you react. She stops answering, it dies. You handed her the steering wheel and then wondered why you were not driving.
Start from something she actually put up
The easiest fix costs nothing. Before you type anything, find one specific thing on her page and build off that.
Not her face. Every man sent that. The photo taken somewhere odd, the line about her terrible sense of direction, the dish she claims to make better than her mother. One of those is a door, and walking through a door she opened herself is far easier than knocking on a wall.
The difference in what comes back is not subtle. "How's your week going" gets a polite nothing. "That is the second Wednesday-night bouldering photo I have seen today, is the gym in the old warehouse" gets an actual answer, because she has something she wants to say about it.
Ask about choices, not categories
A question about a category asks her to file herself. A question about a choice asks her to tell you about a decision she made, and people enjoy that far more than they enjoy being classified.
Category: what kind of music do you like. Choice: what was the last show you went to that was actually worth the queue.
Category: do you travel much. Choice: where did you go that you would happily go back to tomorrow.
Category: what do you do. Choice: what part of it would you keep if the money were identical either way.
The second version in each pair gets a story rather than a label, and a story gives you five things to respond to instead of one.
Answer your own question in the same message
This one move stops the interview feeling on its own, and hardly anybody does it.
Ask, then answer. "Best thing you have eaten this month. Mine was a mediocre kebab at 2am that I would defend in court." Now she knows something about you, she has a benchmark to beat, and you have shown her the size of answer you are after.
It also stops the exchange going flat when she is busy. A line that carries your own answer is worth reading even if she never replies to the question, so it earns something either way.
The questions to stop asking
Some questions are so worn that sending one is a small tell about how much thought went in.
How's your day. What are you up to this weekend. Hey, how are you. Any of those on their own is survivable. As an opener it is a coin flip she has no reason to call.
Then there is the second group, the ones that are too much too early. Why are you single. What happened with your last relationship. What are you looking for on here. Each of those is a fair question three exchanges before a date and a strange one from a stranger on day one.
Guess instead of asking
A guess does everything a question does and carries a bit of personality with it.
Instead of asking where she grew up, say she reads like somebody who grew up somewhere with weather. Instead of asking whether she cooks, say the kitchen in her photo looks like it either gets used every day or has never been touched. If you are right she will tell you. If you are wrong she will correct you, which is a better reply than a right guess gets.
Keep the guesses light and keep them about choices rather than character. A playful wrong guess about her hometown is fun. A confident wrong guess about who she is as a person is not.
Use what she gives you to set up the invitation
Every question has a second job, which is to hand you a reason to ask her out.
She mentions the bouldering gym. She mentions she has never found a decent Thai place on that side of the river. She mentions the exhibition she keeps meaning to see. Each of those is a specific evening you can propose without inventing anything, and a specific evening is much easier to say yes to than "we should grab a drink sometime".
So after a few good exchanges, stop asking and start suggesting. The questions were never the point. They were how you found the thing to invite her to.
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.