Dearly Diary
Questions to Ask a Friend to Deepen the Friendship
For the people you already have — and the conversations you keep not quite having.
8 minute read · Conversation & Connection
There is a particular friendship that has lasted a decade and rarely leaves the surface. You know their job, their partner, the state of their kitchen renovation. You could not say what they are frightened of, or what they would do differently.
Nothing is wrong. You simply fell into a groove early on — logistics, updates, the news — and grooves are hard to climb out of without seeming to make a thing of it.
Questions are the way out, though not the kind you would ask a stranger. With a new acquaintance, a good question is an introduction. With an old friend, it is an invitation to go somewhere you have both been circling for years.
If you are at the other end of the process — someone new rather than someone old — the 36 Questions are built for that, and this collection is not.
How to Ask Without Interrogating
Ask one, not a list
The fastest way to make a friend uncomfortable is to move through questions like a form. Ask one, then stay in it. Most of the value is in the third answer, not the first.
Answer it yourself too
A question you would not answer is an interrogation. Going first — or straight after — makes it a conversation and tells them how deep you actually meant.
Choose the right container
Side by side beats face to face. Walks, drives, washing up, the last hour of a long evening. Difficult things get said far more easily when nobody is required to hold eye contact.
Let a pause be a pause
A real question needs thinking time. If you fill the silence with a second question, you have just taken back the offer.
Take no for an answer, warmly
“I don’t know” and a change of subject are both complete replies. Accept them without comment and the door stays open for another day.
The Questions, by What They Are For
When you want more than “fine, busy”
- What has been taking up most of your head lately — not your time, your head?
- What is something good that happened this month that you have not told anyone about?
- What are you quietly dreading?
- Is there anything you have been putting off telling me?
- How are you, actually — the long version?
- What has been harder than you expected this year?
Looking back together
- What do you remember about the first time we met?
- What were you like at nineteen, and what would you say to them now?
- Which version of yourself do you miss?
- What is a decision you made years ago that you are still glad about?
- Who shaped you the most, and do they know it?
- What is a story from your childhood I have never heard?
What they are moving toward
- What would you like the next five years to feel like — not look like?
- What is something you want that you feel slightly silly wanting?
- If money and logistics were solved, what would you do with a year?
- What would you like to be better at by this time next year?
- What are you hoping somebody asks you about?
About the friendship itself
- What do you need from your friends that you rarely ask for?
- Am I easy to reach when things are bad?
- Is there anything you wish we did more of?
- What is something I have said or done that stayed with you?
- How do you like to be looked after when you are struggling?
- What do you think I am wrong about?
Lighter, and still revealing
- What is the best thing you have eaten this year?
- What have you changed your mind about recently?
- What is your most irrational loyalty?
- What would your ideal ordinary Saturday be, start to finish?
- What is something you are secretly very good at?
- What is the last thing that made you laugh until you could not speak?
When they are having a hard year
- What would actually help this week — company, distraction, or nothing?
- Do you want me to listen or to help you think it through?
- What are you tired of explaining to people?
- Who else knows about this?
- What would you like me to remember to ask you about next month?
Asking in Writing
Some questions are easier to receive on paper. A letter gives your friend a week to answer, in private, without their face doing anything in the meantime — and people say things in ink that they would talk their way around in a kitchen.
It also removes the awkward machinery of the ask. You are not turning the evening serious; you are simply writing, and a question sitting in the middle of a letter is easy to answer or easy to leave.
If you write to someone this month, put one real question in. Not six. Ask it plainly, tell them something true first so the exchange is even, and then wait — which is the whole pleasure of letters anyway.
If the page tends to go blank on you, the Diary has a guide to what to write in a letter — and one on keeping a far-away friendship alive.
Somebody Has to Ask
You do not need a deck of cards or a special occasion. You need one question, asked by someone who genuinely wants the answer, and the patience to sit through the silence before it arrives.
Most long friendships are not waiting for more time together. They are waiting for somebody to ask.
A gift from the Diary
36 Questions Worth Asking Someone You Want to Know Better
A free guide from Dearly, made to keep close. For first letters, long drives, old friends, and the conversations you wish lasted longer.
Wish you had someone to write to?
Dearly thoughtfully pairs people for handwritten correspondence, and carries the letters between them — no addresses exchanged.