MiddleSpot / Questions to ask your friends

Fifty questions to ask your friends

Most friendships run on the same ten topics. These are for the other conversations, the ones you would have if someone else asked first. Read one out at dinner, drop one in the group chat, or write your answer down and swap.

Easy warm-ups

For a table that has not quite settled yet.

What is the best meal you have eaten this year, and who was it with?
What is a small thing that always makes your day better?
Which skill would you give yourself overnight?
What is the most useless thing you are good at?
What did you want to be when you were ten?
What is the last thing that made you laugh until it hurt?
Which song do you play when you need to feel like yourself?
What is a smell that takes you straight back to somewhere?
Which book or film do you keep recommending to people?
What would you do with a completely free Tuesday?

Getting to know you

A little more personal, still easy to answer.

What is something you are quietly proud of?
What do you do when you cannot sleep?
What is something you changed your mind about this year?
Who taught you the most without meaning to?
What is a habit you picked up from your family?
What do you find hard to ask for?
When do you feel most like yourself?
What is something you pretend to understand?
What did you believe at twenty that you have quietly dropped?
What is a compliment you still remember?

Memories

Good for long evenings and long drives.

What is a place that feels like home to you?
What is your earliest memory?
Which year of your life would you go back to for a day?
What was the best advice you ignored?
What is a trip, a night or a meal you think about more than you expected to?
What is something you kept from childhood, and why?
Who is someone you lost touch with and still think about?
What was the first thing you bought with your own money?
When were you scared and glad you did it anyway?
Which moment of this past year do you want to keep?

What if

Hypotheticals, for when the real answer needs a way in.

If you could have dinner with anyone you have never met, who would be at the table?
If you woke up tomorrow in a different city, which one would you hope for?
If you had to teach a class on anything, what would you teach?
What would you do if you knew nobody would judge it?
If you could ask your future self one question, what would it be?
If your life were a book, what would this chapter be called?
Which rule would you change in the world, for one week only?
If money and time did not matter, what would you be working on?
Which object in your home would you grab if you had to leave quickly?
If you could unlearn one thing, what would it be?

For friends you have known for years

The ones that only work with someone who already knows you. Handle with care.

What is something you have been meaning to say to me?
What is your favorite memory of the two of us?
What is something I do that you would miss?
When did you last feel really understood, and by whom?
What is one thing you would like us to do more of?
What did you think of me when we first met?
What is something small I did that you never forgot?
What do you think we will be arguing about when we are eighty?
What is something you are worried about that you have not said out loud?
What is the best thing happening in your life right now that you have not told anyone?

Three ways to use them

Out loud. Read one, let it sit, and answer it yourself before anyone else does. Going first makes it easier for everyone after you.
In the group chat. Post one question a day. Short answers are fine. The best ones tend to arrive a few hours later.
In writing, then swap. Everyone writes their own answer first and nobody reads anyone else’s until all are in. People answer more honestly when they cannot see what the last person said.

Keep the swap going

MiddleSpot is built around the third way. A question arrives, everyone writes their own answer, and a page stays sealed until you have written yours. It also has decks of questions like these for when you are already sitting together. Your first shared journal is free.

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Questions about the questions

What are good questions to ask a friend you do not know well yet?

Start with the warm-ups: a favorite meal, a song, a place that feels like home. They are easy to answer and tell you more than they look. Save the harder sections for when someone has already shown they like talking.

How do I start a deep conversation without it feeling forced?

Answer the question yourself first, honestly and briefly. Asking something you are willing to answer is what keeps it from feeling like an interview.

What can I ask a friend who lives far away?

Anything here works in writing. The memory questions and the ones about the two of you do especially well when you cannot be in the same room. A shared journal sends one question every week or month, so it does not depend on remembering to ask.