What to Ask on a First Date From a Dating App

Start from something she already told you, then ask about choices rather than facts. The questions that work get her talking about a decision she made, take a sentence to answer, and come back with something of yours attached. Job, hometown and siblings are not questions. They are a form, and she has filled it in twice this month.

You are not meeting a stranger. You are meeting a woman you have already exchanged a few dozen lines with, and the worst thing you can do in the first five minutes is pretend otherwise.

Pick one thing she mentioned and open on it. She was dreading a work trip: ask how it went. She claimed the place near her apartment does the best coffee in the city: tell her you checked and you have a rival candidate. It signals you were paying attention, and it skips the awkward reset where two people who have been talking for a week start again at "so, what do you do".

If you cannot remember anything she said, read back through before you leave the house. Two minutes, and it changes the first ten.

A fact question asks her to report. A choice question asks her to explain something she decided, and people are far more alive when they are explaining a decision.

"What do you do" is a fact. "What would you keep about the job if the money were the same either way" is a choice.

"Do you travel much" is a fact. "Where have you been that you would go back to tomorrow" is a choice.

"Where did you grow up" is a fact. "What did you like about growing up there that people who did not grow up there never get" is a choice.

The second version in each pair gets you a story, an opinion, and something to disagree with. The first gets you a word.

The single easiest way to stop a date feeling like an interview.

Ask, then give your own answer before she has to ask for it. "Worst job you ever had. Mine was six months in a call center selling boilers to people who already had boilers." You have set the size of the answer, shown her the level of honesty on offer, and given her something to react to whether or not she answers the question at all.

Men skip this because they think the date is about learning about her. It is not. It is about finding out whether the two of you are good company, and that requires both of you to be in the room.

A guess is a question with personality attached, and it changes the temperature of a table fast.

"You strike me as the youngest of three." "I am guessing you are the friend who books everything and then complains about organizing it." "You have absolutely moved cities at least twice."

If you are right, she tells you how you knew. If you are wrong, she corrects you, and a correction is a longer and warmer reply than a right guess gets. Either way she is talking about herself without being questioned about herself, which is the whole trick.

Keep the guesses to habits and circumstances. Confident guesses about her character land badly when they miss.

Silences happen and they are not a verdict. What matters is what you reach for.

Do not reach for another fact question, because that restarts the interview. Reach for something present instead. What she thinks of the place you are in. Which of the two things on the menu she would pick for you. The couple at the next table who have clearly had this argument before.

Asking about now beats asking about her history, because now is shared and her history is homework.

Some questions are fine later and expensive on a first evening.

Why are you single. What happened with your last relationship. How long were you together. What are you looking for on here. Each of those turns the table into an assessment, and assessments are not attractive, whichever direction they run.

The same goes for the ladder of logistics: how far is your place, do you live alone, are you seeing anyone else. Those get answered by the evening itself if the evening goes well.

Listen for two things and you will know what to do at the end.

The first is whether she gives you more than the question asked. A woman who is enjoying herself over-answers. She adds the detail nobody requested, and that is the clearest signal on the table.

The second is anything you can build a second date on. She mentions a restaurant she has never got round to, a band coming through in April, a thing she has always meant to try. That is your next invitation, and you will only catch it if you stopped planning your next question long enough to hear it.