Questions to ask on a date.

To start with

Easy to answer, and hard to answer in one word. Good for a first letter.

1. What’s been on your mind this week? Small things count.
2. What are you a little obsessed with at the moment? It doesn’t have to be anything impressive.
3. Walk me through your perfect day off, hour by hour. The kind you’d really have, lie-in included.
4. What’s the last really good thing you read, watched or listened to? What made it so good?
5. What are the small, everyday things that make you happy? I’d love a list of ten.
6. Take me to a restaurant you love and order for me. What are we having?
7. Tell me about a petty victory you’re still enjoying.
8. What’s the most useless skill you have that you’re secretly proud of?
9. What did you believe as a child that turned out to be completely wrong? How old were you when you found out?
10. Make me a playlist of five songs for a long drive at night, in the right order.
11. What would twelve-year-old you make of your life now? What would they love, and what would horrify them?
12. What’s the smallest hill you’re willing to die on?

Once you’ve been writing for a while

These ask for a little more of you in the answer.

1. What does an ordinary good day look like for you?
2. What are you quietly proud of that probably wouldn’t impress anyone else?
3. What’s the last thing you really changed your mind about? What did it?
4. Is there a book, film or album you keep going back to? What do you get from it each time?
5. Is there somewhere you’ve never lived that you still feel homesick for? Why there?
6. You can invite any three people, living or dead, to dinner. Who comes, and who does the cooking?
7. If you had to open a little shop tomorrow, what would it sell, and what would you call it?
8. Plan a Saturday with nothing you have to do and no phone. How would you spend it?
9. Imagine a letter from yourself, ten years from now. What do you hope it says?
10. If you never had to worry about money again, what would you change in your life by the end of the week?
11. How would your oldest friend describe you, if they were being completely honest?
12. What about you hasn’t changed at all in the last ten years? Are you glad it hasn’t?

When you trust each other

These take some honesty. Only ask one you’d be willing to answer yourself.

1. When did you last feel really understood by someone? What did they do that made you feel that way?
2. What scares you, really? Tell me as much or as little as you like.
3. What’s been your hardest year so far, and what got you through it? Tell me only as much as you want to.
4. What’s the best decision you’ve ever made? Did you know it at the time, or only later?
5. When do you feel loneliest, and does having people around help?
6. What do you need to hear at the moment, and who would you want it from?
7. What’s one thing you know about loving someone that you’d want to pass on? Did you learn it the hard way?
8. What do you wish people understood about you without you having to explain?
9. What did you get from your family that you’re glad of? And is there anything you’re trying to unlearn?
10. What lesson do you keep having to learn over and over? Are you getting any better at it?
11. What do you hope the next five years hold for you? The specific things, if you can.
12. What are you like when you’re on your own? Are you different from the person your friends see?

Two things that make a question land

Answer it too. A question feels like an interview when only one of you has to answer. On Textrodate, whoever asks also answers, and answers last, so nobody asks what they wouldn’t answer themselves.

Let them skip it. Anybody can pass on any question, without saying why. That takes the pressure off the ones they do answer.