She said yes to a drink. You wrote back "where do you fancy?" and the conversation has been sitting there for two days.
It did not die because she went off you. It died because you handed her homework.
You pick, and it is not close
For a first date from an app, you choose the place, you choose two times, and you send both in one message. That is the whole answer, and almost every problem in this article comes from not doing it.
"There's a wine bar on Dean Street I like. Thursday or Saturday, whichever works better for you?"
That message takes her four seconds to answer. She either picks a day or she tells you neither works and offers another. Both of those are a live date. Compare it with "what are you up to this week and where do you want to go?", which takes her real thought at a moment she is probably on a bus.
What "wherever you like" actually asks her to do
Men think they are being easy going. What she receives is a list of tasks.
She has to think of somewhere. She has to guess your budget, because if she names somewhere expensive she looks like she is taking advantage and if she names a chain pub she looks like she is not bothered. She has to guess how much effort you want the evening to be. She has to work out which area is fair for both of you. Then she has to send all of that to a man she has never met, who might read it wrong.
That is four decisions she never asked for, all of them with a small social risk attached, for a night out she is maybe sixty per cent sure about. Quite often she just does not reply, and you spend the rest of the week trying to work out what you said.
There is a second thing it signals, and this is the one that actually costs you. A man who cannot pick a bar has told her, before they have met, that every plan for the next month is going to be her job.
Pick somewhere near her, not near you
This is the part men get backwards.
Picking the place is yours. Picking the area is mostly hers, and you should do that work for her without making her ask. If she lives in one part of town and you live in another, choose somewhere on her side, or a genuine halfway point.
The reason is simple. A date that is fifteen minutes from her flat is a small yes. A date that is an hour away on a Wednesday is a big yes, and big yeses get cancelled on Wednesday afternoon. You are not being chivalrous, you are removing the excuse that kills the booking.
If the distance is real in both directions, say so out loud and split it. "You're east, I'm west, so let's meet in the middle. There's a place by the station, Tuesday or Thursday?"
What to actually pick
A bar, a decent pub, a wine bar, a cocktail place. Somewhere you have been before, so you know where the door is, whether there are seats at seven, and what you are going to order.
Keep it to drinks. Not dinner, not an activity, not anything that runs three hours or costs seventy pounds. A drink can turn into dinner if the evening is good, and it can end cleanly at eight if it is not. Dinner cannot do either.
Somewhere you have been also solves the small disasters. If the place is rammed, you already know the other bar around the corner, and moving there without breaking stride is worth more than the perfect venue.
Two options, not twenty
Send one place and two times. That is it.
Three venues and a week of availability is not generosity, it is the same homework problem in a different shape. Every extra option is another small decision you have handed her, and each one is a chance for the conversation to stall while she works out which answer is right.
If she cannot do either time, she will say so. That is not a rejection, it is a reschedule, and it takes one more message.
Where men take this too far
The other end of this is worse than asking, because it is harder to recover from.
There is a version of "I'll pick" that is really "I have decided and you are coming". A man books a restaurant without checking, names a single evening with no alternative, or brushes past the one thing she actually said she wanted. Decisiveness is attractive. Being managed is not, and she cannot tell those two apart until she is already out with you.
The difference is a single clause. "There's a place on Dean Street I like, Thursday or Saturday?" is a plan with a door in it. "I've booked us in for Thursday at eight" is a summons.
And when she does have a preference, take it. If she says she does not drink, or she cannot do that side of town, or she would rather do a coffee first, move without making a thing of it. The point of picking was to save her effort, not to win the choice.
When the venue was never what went wrong
Sometimes you do all of this properly and the date still never gets booked. That is worth knowing about, because the answer is usually a few messages earlier than the venue.
The ask lands badly when the conversation had gone flat, or when it comes twelve messages too late, or when it is phrased so carefully that she cannot tell whether you are asking her out or making small talk. You cannot see any of that in your own messages, because you knew what you meant when you typed them.
An hour on a call with a coach, with your last few conversations open in front of him, is usually enough to name the thing you keep doing. Not a rewrite of one message, but the habit underneath it, and how to send the ask so that picking a bar is the only decision left.
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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