First Date Questions to Ask a Woman

Ask the question that fits what you want to find out. That might be what she gets excited about, how she treats people, what she wants from her life, or whether the two of you click. Use one at a time, answer it yourself, and follow whatever she says instead of reading from a list. A question is only as good as the story it gets back.

Most men grab a list and read down it. That is how a date turns into an interview. Pick the question by what you want to learn, then ask the one that fits the moment.

To see what lights her up

Ask about something she does, not what she does for a living. People talk better about what they love than about their job.

• "What do you do when you have a completely free Saturday?"
• "What is something you could talk about for an hour without noticing?"
• "What is the best thing you have made, cooked or fixed lately?"

Watch her face when she answers. My advice on hobbies is that a list of facts leads to friendship, while the feeling behind the hobby builds connection. If she lights up, ask what she likes about it, not how long she has done it.

To see how she treats people

You learn this from stories about others, not from a direct question.

• "Who is the person in your life you would drop everything for?"
• "Tell me about a friend who makes you laugh."
• "What is the nicest thing someone did for you this year?"

Notice whether she talks about people with warmth and whether the stories always have a villain.

To see what she wants

This is what coach calls qualifying, and his point is that you should walk in knowing what you are looking for. Does she want adventure or calm, a career or a quiet life, kids someday or not? You do not interrogate her. You ask lightly and listen.

• "Where do you want to be living in five years?"
• "What would make this year a great one for you?"
• "What does an ideal week look like for you?"

If her answers and yours point in different directions, that is useful to know early, and no one has done anything wrong.

To flirt a little and keep it playful

These are the ones that make it a date and not an audition.

• "What is your most useless talent?"
• "What is the best surprise you have ever had on a night out?"
• "What would you order if nobody was judging you?"

Tease her answers a little. A small push, like "You say you hate small talk, and you have used the weather twice," keeps it light.

My rule is that the question should carry some insight or personality of its own. "What do you do?" asks her to supply everything. "You seem like someone who would hate a desk job, so what do you actually do?" gives her something to react to, and it shows you were looking at her.

Better still, answer it first, or turn it into a guess: "You look like you grew up near the water. Am I close?" Then she is correcting you, not filling in your form.

His other warning is about count. One boring question is fine, two is tiring, three in a row usually ends it. Follow each answer with a comment or a story before you ask anything else.

Start with the playful ones, because she is still deciding how relaxed to be. Once she is laughing, move to what lights her up. Save the wants questions for the middle of the date, when she trusts you a little. Leave the last ten minutes for the two of you, not for questions: tease her, say what you liked, and make a plan.

• Anything about her ex, her number of partners, or why she is single. coach says past relationships are risky ground, and they make her feel evaluated.
• Questions that show you have already decided, like "so are you looking for something serious?" in the first ten minutes.
• Heavy politics or religion. coach keeps both off dates.
• Her salary, her age, or her family's money.

A good question is half the job. The other half is what you do with the answer. Repeat one word she used, ask what happened next, or tell a short story of your own that matches. If she mentions something she wants, remember it. A line like "You said you wanted to try that ramen place" is the strongest reason to ask her for a second date.