Questions to Ask Pen Pal
Questions for a one-to-one correspondence that you want to keep going for years rather than months. Ordered from the kind of thing you can ask in a first letter to the kind that only works once you have been writing for a while.
The questions
Open any question for the note
What can you see from where you are sitting to write this?
Why ask it
A first-letter question that is almost impossible to answer boringly, because it forces detail: a courtyard, a bus stop, a cat on a wall. It also sets a tone of specifics rather than summaries, which is what makes letters worth keeping.
What sound do you hear most often where you live?
Why ask it
Nobody has an answer prepared, so you get something genuinely observed. It tends to open onto neighbors, traffic, weather, and animals without needing a separate question about any of them.
What did you do today, in as much detail as you can stand?
Why ask it
The permission to be dull is what makes this work. Ordinary detail is the thing that makes a distant person feel real, and it gives you something to ask about next time.
What happens in the first hour after you wake up?
Why ask it
Routine is easier to write about than personality and reveals more of it. You learn about their household, their commute, what they eat, and whether their mornings are their own.
What do people your age do on a Friday night where you are?
Why ask it
Broader than asking what they do, so it works even if the honest answer is nothing much. The gap between what everyone does and what they do is usually the interesting part.
If you could post me one thing from a shop near you, what would it be?
Why ask it
A concrete and slightly playful question that gets at food, local pride, and taste all at once. It also frequently leads to an actual parcel, which is one of the pleasures of a paper correspondence.
What is something completely ordinary where you are that you think would seem strange to me?
Why ask it
Puts them in the position of noticing their own surroundings, which most people enjoy. It produces more interesting material than asking directly about culture, because it aims at the unremarkable.
Is there a word in your language you wish English had?
Why ask it
Works for anyone bilingual and tends to produce something genuinely useful to know. If you share a language, ask about a local word or phrase from their region instead.
What did you want to be when you were eight?
Why ask it
Easier to answer than a question about ambition, and often funnier. What they say next about why it changed is where the actual information is.
Who taught you something you still use?
Why ask it
Brings in a person rather than a trait, so you get a story with someone in it. Grandparents, teachers, and first bosses come up often, and they open the door to family without asking about family directly.
What are you reading or watching at the moment, and are you actually enjoying it?
Why ask it
The second half is what saves this from being a favorites question. Permission to say it is boring produces a real opinion, and shared abandonment of the same book is a better bond than shared praise.
What do you do when you cannot sleep?
Why ask it
Quietly personal without being intrusive, and it gets at habits, worries, and what they read at 3am. Letters are a good medium for this kind of question because they can answer it whenever they like.
What is something you have kept for no practical reason?
Why ask it
Objects carry stories that people will not tell you if you ask for the story directly. A ticket, a shell, a letter from someone else: the answer is usually short and tells you a great deal.
What do you not like about where you live?
Why ask it
Ask once you are a few letters in. Correspondence often stays relentlessly positive, and this question gives permission to be honest, which is where the friendship starts rather than the pen-pal exchange.
What has happened this month that you have not told anyone about?
Why ask it
Distance makes this easier to answer than it would be face to face, which is the particular advantage of writing to a stranger. Expect a short answer at first and a longer one later in the correspondence.
What are you putting off?
Why ask it
Four words, and almost everyone has an immediate answer. It tends to lead to the thing actually occupying their mind, which a question about their week will miss.
What is the longest you have ever waited for something?
Why ask it
Fits a correspondence that itself runs on waiting. The answers range from a visa to a diagnosis to a bus, and any of the three gives you somewhere to go next.
If you had a free day and a little money, what would happen?
Why ask it
More revealing than asking about dreams, because the constraint makes the answer real. It also tells you what is nearby, what costs money there, and who they would spend the day with.
Where do you think you will be living in five years, and how do you feel about that?
Why ask it
How they feel about the prediction is the point. Many people can forecast their situation accurately and are quietly unhappy about it, and this is the kind of thing more easily written than said.
What have I got wrong about you so far?
Why ask it
Worth asking after several letters, when you have both built a picture. Correcting a misreading usually leads to the most honest paragraph either of you has written, and it prevents a correspondence from settling into a polite fiction.
What would you like me to write about next time?
Why ask it
The most practical question here, because it stops both of you drifting into weather and pleasantries. Most people ask for something specific, and it removes the blank-page problem from your next letter.
Keeping a Correspondence Going
Practical guidance for the conversation itself
What Makes Letters Worth Reading
Answer before you ask
Respond to what they wrote, in order, then add your own news, then ask one or two questions. Letters that are only questions read like a form, and letters that ignore the previous one make people stop writing.
Two questions per letter, not ten
A long list forces short answers to each. Pick one easy question and one that takes some thought, and save the rest. A correspondence that lasts years does not need to cover everything in month one.
Prefer the specific to the general
What did you eat yesterday gets a better answer than what food do you like. Detail is what makes someone thousands of miles away feel like a person rather than a profile.
Match their length and pace roughly
If they send one page every three weeks, four pages every four days will feel like pressure. Settling into a rhythm that suits the slower writer is what keeps the exchange alive.
Send things, not only words
A postcard of your street, a pressed leaf, a ticket stub, a photograph of something dull. Small enclosures are half the appeal of paper post, and they answer questions you did not think to ask.
Keep their letters somewhere
A box or a folder is enough. Being able to reread what they told you last spring is what lets you follow up on the exam, the move, or the sick relative, which is what makes a correspondence feel like a friendship.
What Kills a Correspondence
- Interviewing. Page after page of questions with nothing about yourself puts all the work on them and gets shorter and shorter replies.
- Waiting until you have time to write properly. A short honest letter now beats a long one you never send, and most correspondences die in that gap rather than from any decision.
- Only writing when things are going well. A letter that says this month was hard and here is why is usually the one that turns an exchange into a friendship.
- Asking heavy questions in a first letter. Politics, religion, income, and family trouble need a few rounds of ordinary letters behind them.
- Assuming silence is rejection. Post goes missing, people get ill, life gets busy. One gentle follow-up after a couple of months is reasonable.
- Correcting their English unless they have asked you to. Most people writing in a second language want conversation rather than a lesson.
Practical Notes
- Check international postage rates and weight limits before you write six pages. Aerogrammes and thin paper make a real difference to cost.
- Date every letter. When post takes three weeks each way, the dates are the only way to keep the conversation in order.
- Number your letters if delivery is unreliable, so you both know when one has gone missing.
- Food, seeds, and some other items are restricted or prohibited by customs in many countries. Check before enclosing anything other than paper.
- If you are writing to a child, or you are under eighteen yourself, go through a school programme or an established organization and use their address rather than a home one.
- Never send money, and be cautious with anyone who moves quickly to requests for it. This is the most common way pen-pal arrangements go wrong.
- If the correspondence has run its course, say so in a short kind letter rather than fading out. It is a small courtesy and people remember it.