Questions to Ask in a Letter
Questions to put in a handwritten or emailed letter to a friend, a relative, or a pen pal, chosen because they reward a long answer written slowly rather than a quick reply. Includes light openers and a few that go further, plus advice on how many to ask at once.
The questions
Open any question for the note
What does your week look like right now, hour to hour?
Why ask it
A letter gives someone room to describe the shape of their days, which is what you actually miss about a person you no longer see. It also lets them write easily, which matters most in the first exchange or after a long gap.
What is on your walls, your desk, and your fridge these days?
Why ask it
Small and physical, so it is easy to answer at length, and the details do more work than a summary would. People tend to write about the photograph or the ticket stub and then about the person or the day it came from.
What have you been doing lately that you did not expect to enjoy?
Why ask it
The surprise is what makes this different from asking about hobbies. Answers tend to arrive with a story about how they started, and they show you who someone is becoming rather than what they already told you they like.
Who have you seen recently that I would remember?
Why ask it
It draws on shared history without requiring you both to reminisce, and it usually produces news you would never have thought to ask about. In long correspondences this is the question that keeps you inside each other's world.
What are you reading, and would you send it to me if you liked it?
Why ask it
The second half turns a question into an exchange, and a book arriving in the post gives the correspondence its own momentum. It also gives you something specific to write about next time.
What have you changed your mind about since we last talked?
Why ask it
This is a question people rarely get asked and often want to answer. In writing they can be tentative in a way conversation does not allow, and the answers are frequently about something larger than the topic itself.
What are you saving toward?
Why ask it
Money and plans are often easier to write than to say. The answer might be a trip, a deposit, a course, or nothing at all, and each version tells you where the person thinks their life is heading.
What would you do with a free Saturday and nothing you had to do?
Why ask it
Light on its face, but the answer is a good measure of how tired someone is. When people describe sleeping and an empty house rather than an outing, that is worth noticing in your reply.
What do you miss about where you used to live?
Why ask it
Works with anyone who has moved, and produces detail rather than sentiment: a bakery, a walk, a neighbour, a bus route. It often opens into what they have not managed to rebuild in the new place.
Which of our old jokes do you still use?
Why ask it
It is a way of saying that the shared past is still live without becoming solemn about it. Answers usually come back with an anecdote about who they used it on and whether it landed.
What are you working on that nobody around you cares about as much as you do?
Why ask it
Almost everyone has one of these, and being asked about it is rare enough to feel like a gift. The answer tends to be several pages long, which is exactly what a letter is for.
What is the last thing that made you laugh out loud when you were on your own?
Why ask it
Specific, easy, and it produces something you would never otherwise learn. Asking about being alone rather than in company gets you their actual taste rather than the version they perform.
Who in your family have you been thinking about?
Why ask it
Broad enough to be safe and pointed enough to matter. It leaves room for an ageing parent, an estranged sibling, or a child doing well, and it lets them choose which one they are ready to write about.
What advice did someone give you that you ignored? Were they right?
Why ask it
The second half is what makes this land, since it asks for a judgment rather than a story. In writing people are unusually willing to concede the point, which is a kind of honesty conversation rarely reaches.
What do you want to be true about your life a year from now?
Why ask it
Better than asking about goals, because it allows for circumstances rather than achievements: living somewhere else, being less tired, having finished a thing. Keep their answer and ask about it next year.
What has been hard lately that you have not told anyone?
Why ask it
A letter is the right medium for this, because they can answer at their own pace or leave it and you will not be sitting there waiting. Do not ask it in a first letter, and if they answer, respond to that before anything else.
How are you sleeping, and what is on your mind when you wake up?
Why ask it
More specific than asking how someone is, and much harder to answer with one word. It reaches straight for what they are worrying about, so ask it only where the friendship can carry the answer.
What do you wish I would ask you about?
Why ask it
It hands the correspondence over to them, and the answer often reveals what your last few letters have been talking around. People sometimes name something they have been waiting to be asked for years.
What should I know about how you are really doing, not the short version?
Why ask it
Naming the short version explicitly is what gives permission to skip it. Ask it once you have earned it, and be prepared to receive an answer that needs a real reply rather than reassurance.
What should I write to you about next time?
Why ask it
It keeps the exchange going, which is the hardest part of any correspondence, and it tells you which parts of your last letter they actually wanted more of. Answer whatever they name, first thing in your next letter.
Asking questions in a letter
Practical guidance for the conversation itself
How many, and where to put them
Two or three per letter, no more
A list of ten reads like a form and usually gets none of them answered. Two or three, spread through the letter rather than stacked at the end, get real answers because the reader can hold them in mind while they write.
Answer theirs first
Open by responding to what they asked you last time, in detail. Correspondences die when one person only asks and never gives, and the imbalance is more obvious in writing than in conversation.
Earn the harder questions
Ask what is going wrong in someone's life after a few exchanges, not in the first letter. The order matters more in writing, because a stranger's question about your worst month is easy to ignore and easier to resent.
Say why you are asking
A sentence of context turns a question into part of a conversation rather than a prompt. Say that you have been thinking about a place you both lived, or that you noticed they went quiet about work in the last letter.
Practical details
- Date the letter. In a slow correspondence, months pass and the sequence stops being obvious.
- Keep questions on separate lines or at the end of paragraphs, since a question buried mid-paragraph is the one that gets missed.
- Leave your own news in. A letter that is only questions puts the work on the other person.
- Ask open questions rather than ones answerable with a yes, which in a letter costs you a whole exchange.
- Keep a note of what you asked. If a reply skips a question, you can decide whether to raise it again or let it go.
What makes a letter hard to answer
Stacked questions
Three questions in one sentence usually get one vague answer covering all of them. Split them across the letter, or drop two.
Questions that need a phone call
Anything urgent, anything requiring back and forth, and anything you would want an immediate reaction to belongs in a call. Letters are poorly suited to negotiation and to conflict.
Pressing on silence
If someone skips a question twice, they have answered it. Asking a third time in writing, where it sits on the page, reads as pressure.
Asking for an update on something painful without an offer
A question about an illness, a job loss, or a separation lands better alongside something concrete: a visit, a phone call, a specific offer of help.
Adjusting for who you are writing to
- A new pen pal: stay concrete and light, ask about days and surroundings, and let the deeper questions wait several exchanges.
- An old friend you have lost touch with: lead with your own news, then ask one question about now rather than one about the gap.
- A grandparent or older relative: ask about a specific period or object rather than their life in general, which is easier to answer and produces better stories.
- Someone in prison or hospital, or serving overseas: ask about the ordinary parts of their day, and keep news of home in the letter, since questions alone can be hard to answer from inside a constrained routine.
- A child: one question is plenty, and something they can draw an answer to works better than something they must explain.