Questions to Ask Your Pen Pal
Questions built for letters rather than conversation, for a new or long-standing pen pal, moving from concrete details about their day and their street to the things people write more easily than they say.
The questions
Open any question for the note
What can you see from where you are sitting as you write this?
Why ask it
It gives a reply a starting point that needs no thought and produces a picture you could not have asked for: a courtyard, a bunk, a car park, a cat. Letters answered from a specific place read completely differently from ones written in the abstract.
What time do you get up, and what is the first thing you do?
Why ask it
Routine is the easiest thing in the world to describe and it quietly conveys work, family, religion and money. It also gives you something to refer back to in later letters, which is how correspondence starts to feel like friendship.
What does your street sound like at night?
Why ask it
Sound is rarely asked about and always available, so almost nobody gives a short answer. Traffic, insects, a neighbour's television or complete silence tells you more about where they live than a description of the town would.
What did you eat yesterday, all of it?
Why ask it
All of it is the part that works, because it rules out the tourist-brochure answer about national dishes. You get the snacks, the leftovers and the thing eaten standing up, which is what daily life actually looks like.
What food from where you live do outsiders usually get wrong?
Why ask it
Asking what people get wrong invites correction, which is easier and more fun to write than praise. Expect strong opinions about how something is named, made or eaten.
What do people your age do on a Friday there?
Why ask it
Anchoring to their age group avoids a generic account of local culture. The answer tells you what is affordable, what is permitted and how much of it happens at home.
Where would you take a visitor first, and why that place rather than the famous one?
Why ask it
The second half is what stops this being a list from a guidebook. People choose somewhere with a personal reason attached, and the reason is usually the story.
What is everyone complaining about this time of year?
Why ask it
A better weather question than asking about the climate, because complaint is specific and funny. It also picks up harvests, exams, holidays, elections and whatever is currently in the news there.
What are you studying or working on at the moment?
Why ask it
Straightforward, but ask what they are working on rather than what they do, so you get the current task rather than a job title. That gives you something to follow up on next time.
What do you carry with you everywhere?
Why ask it
Small, physical and easy to answer, and it produces the details that make a person real: a key, a photograph, a charm, a notebook. It works particularly well early in a correspondence.
What is something everyone where you live knows that I almost certainly do not?
Why ask it
It gives them the position of authority, which most people enjoy and few letters offer. Answers range from a piece of history to a piece of etiquette you would have got wrong.
What are you listening to enough to be slightly embarrassed about?
Why ask it
The embarrassment clause is what stops you getting a curated list. Ask them to send a title you can look up, since sharing something you can both hear turns two monologues into a conversation.
Is there a word in your language you wish existed in mine?
Why ask it
Almost everyone has one, and explaining it requires them to describe a feeling or situation in detail. This is the question most likely to produce something you remember years later.
What did you think my country was like before we started writing?
Why ask it
It invites honesty about a stereotype, which is only possible once there is some trust. Their answer usually says as much about what reaches them, films, news, sport, as about you.
Who do you talk to most, and what do you talk about?
Why ask it
A gentler route into family and friendship than asking about their family, and it works whether they live with twelve people or alone. Watch for who is missing from the answer.
What did you want to be when you were seven?
Why ask it
Specifying the age produces a real memory instead of a career summary. It also opens the way to what happened to that idea, which is a much bigger question you have not had to ask directly.
Which holiday matters most where you are, and what actually happens on the day?
Why ask it
Asking what happens, hour by hour, gets past the encyclopedia entry to the food, the arguments and the relatives. Ask what they personally do, since not everyone marks the day the official way.
What has changed where you live since you were a child?
Why ask it
Buildings, prices, who lives there, what is no longer possible. This is where a letter shifts from description to something closer to testimony, and it usually arrives with an opinion attached.
Is there something you would rather write than say out loud?
Why ask it
Letters carry confidences that conversation does not, because there is no face to watch and no immediate reply. Only ask once the correspondence is established, and be ready to answer it yourself.
What should I send you, and what would not survive the post?
Why ask it
Practical and worth asking before you post anything: liquids, food, batteries and seeds are restricted in many places, and customs charges can land on the recipient. It also tells you what would actually be welcome.
Writing letters people want to answer
Practical guidance for the conversation itself
How to use these in a letter
Two or three questions per letter, no more
A page of questions reads like a form and often gets no reply at all. Pick a few, answer them yourself first, and let the rest wait for the next letter.
Answer theirs before you ask new ones
Go through their last letter and respond to what they actually wrote, by name and in order. Correspondence dies when one person only asks and never replies.
Number your questions
It makes them easy to answer in order, which matters when your pen pal is writing in a second language or replying weeks later.
Keep sentences short if you do not share a first language
Slang, idiom, sarcasm and long clauses are what get lost. Simple sentences and a small drawing carry further than a well-turned paragraph.
Keep a note of what they told you
Names of siblings, exams, the dog, the job interview. Referring back to something from three letters ago is what makes a pen pal feel known rather than surveyed.
Post, timing and enclosures
- Expect weeks between letters internationally, and do not read a delay as a lost interest.
- Check what you may send before you send it. Food, liquids, seeds and batteries are restricted in many countries, and the recipient can be charged.
- Flat and light travels best: photographs, postcards, a pressed leaf, stickers, a local newspaper page.
- Write the address in the destination country's format, and use a return address on the envelope.
- If postage is expensive for one of you, say so plainly and agree on a rhythm you can both afford, or move some of it to email.
What to avoid
Treating them as a representative of a country
Questions about what your people think put someone in the position of speaking for millions. Ask about their street, their family and their week instead.
Politics in the first letters
It is worth reaching, but not before you know each other, and not as a test. Wait until they raise something and then follow their lead on how far to go.
Sharing identifying or financial details
Never send bank details, passport or identity numbers, and be cautious with anyone who moves quickly to asking for money or gifts. If a young person is writing, an adult should know who the correspondence is with and see the address.
Letting one letter end it
Most correspondences die from a missed reply rather than a falling out. Send a short note rather than waiting until you have time for a long one.