MiddleSpot / First date questions

Twenty-five questions to ask on a first date

A first date goes better when you ask because you want to know, not because you need to fill the silence. These start easy and get a little more personal. Take the ones that suit the evening and leave the rest.

Easy openers

For the first twenty minutes.

What is the best thing you ate this week?
What are you looking forward to?
What did you want to be when you were ten?
Where could you spend a whole day?
What is the last thing you watched that you actually liked?
What does your ideal lazy Sunday look like?
What is the best trip you have taken, and who went?
What is something you are weirdly good at?

Past the CV

Once the job and the neighborhood are out of the way.

What do you do that does not feel like work?
What have you changed your mind about recently?
Who in your life would I most want to meet, and why?
What do you care about that people do not expect?
What was a turning point in the last few years?
What small thing makes a day better for you?
What are you trying to get better at?
What used to scare you?
What does a good friend do, in your book?

When it is going well

Only if the other person is leaning in.

What is the nicest thing someone has said to you this year?
What do you want more of in your life?
What do people get wrong about you at first?
What have you never been asked that you wish you were?
Which book, song or film is a kind of shorthand for you?
What does a good evening look like for you?
What are you curious about at the moment?
What would you like to do next time?

How to ask them

Answer your own question. Say your version first, briefly. It turns an interview into a conversation.
Listen for the follow-up. The second question, the one about what they just said, matters more than the first.
One in three. Mix these in with ordinary talk. A list read out in order feels like a form.

For when you are past the first date

If it goes well, MiddleSpot is a way to keep learning each other without it turning into constant texting. A question arrives, you each write your own answer, and the page opens when both are in. Your first shared journal is free.

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Questions about first dates

How many questions should I ask on a first date?

Fewer than you think. Two or three good ones, each followed up, beat ten asked in a row. Keep a few in your pocket for the lulls.

What should I not ask on a first date?

Anything that sounds like a screening: past relationships in detail, money, what they want in five years. Let those come up on their own.

What if the conversation goes quiet?

A pause is fine. Ask about what is in front of you, the food, the place, how they got here, then go to a question from the list.