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. One group holds the questions to ask a foreign pen pal, on language, time zones and what each country gets wrong about the other, and another keeps the fun questions together for the letter that needs a lighter page.
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The questions
Each question, and why to ask it
Daily life
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 does your day look like, from waking up to going to bed?
Why ask it
The best opening question in a first letter because it is easy to answer at any length. Whatever they linger on, the commute, a sibling, a job they hate, is the thread to pull in your reply.
What is the weather doing today, and is that normal for the time of year?
Why ask it
Sounds like small talk and is genuinely not, because the second half often gets you an aside about a changing season, a harvest or a flood. If you write regularly, this also becomes the pleasant habit that anchors each letter.
How do you get around, and how long does it take you?
Why ask it
Buses, bikes, a long walk, or a lift from a parent. It quietly reveals distance, cost, safety, and independence, none of which anyone answers directly if you ask about them.
What is usually on the table at a family meal?
Why ask it
More useful than asking about national dishes, because it gets what people actually eat on a Tuesday. Ask what they eat when nobody can be bothered to cook, which is where the honest answer lives.
What is on the wall of the room where you write these letters?
Why ask it
Where someone writes from tells you more than what they say about themselves. Posters, a shift rota, a bare wall in a shared flat: each answers a question about their circumstances that would be rude to ask outright.
What is something in your house that I probably would not have in mine?
Why ask it
An object question, which is easier to answer than a culture question and produces better letters. Common answers involve heating, cooling, water, food storage, and religious or family items.
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.
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.
Where they live
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 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 is your hometown known for, fairly or unfairly?
Why ask it
The unfairly half is where the real answer lives, and it lets them complain, which builds more closeness than praise does. Expect a reputation they resent and a detail they are quietly proud of.
What is something completely ordinary where you live that a visitor would find strange?
Why ask it
Invites them to be the expert instead of the exhibit, and the answers are usually specific and funny: a queueing custom, a household appliance, a rule about shoes. Better than asking them to explain their whole culture.
What do outsiders usually get wrong about where you live?
Why ask it
Ask this once you have exchanged a few letters, not in the first one, since early on it can read as a test. Later it is an invitation to correct you, and being corrected gracefully is what makes a penpal trust you.
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 is expensive where you live, and what is surprisingly cheap?
Why ask it
Concrete and comparable, and one of the few ways to talk about money without being intrusive. Fruit, transport, phone data, and rent produce genuinely startling differences between countries.
What is a rule or law where you live that surprises visitors?
Why ask it
Invites them to be the authority on their own place, and the answers range from harmless to revealing. It is also a gentler opening onto politics than a direct question, because they choose how far to go.
Which sport or team does everyone around you follow?
Why ask it
Worth asking even if you have no interest in sport, because the answer maps local loyalties and rivalries. Ask what happens in the town when the team wins, which is where the real description comes.
What is school or university like where you are, in hours and pressure?
Why ask it
Concrete numbers travel better than impressions: how many hours a day, whether Saturdays count, how much a single exam decides. If they mention an exam that determines their whole path, that is worth remembering before you ask casual questions about their plans.
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.
What is a story or song that every child where you live knows?
Why ask it
Gets at the shared background that people forget is local until someone asks. It works particularly well in classroom exchanges, since a whole class can compare their answers.
Which news story is everyone where you are talking about, and what do people disagree about?
Why ask it
Asking what people disagree about, rather than what they think, lets them describe a divided country without declaring a side. If they steer away from it entirely, take that as an answer about their situation and do not push.
What do people your age argue with their parents about?
Why ask it
The universal and the local sit side by side in this answer: phones and curfews everywhere, plus something specific to the place. It tends to be the question that convinces both sides they have things in common.
Foreign pen pal
What language do you use at home, and is it the one you are writing to me in?
Why ask it
Plenty of penpals write in a second or third language and never mention it. Naming it lets them stop worrying about mistakes, and it usually opens the better question of which language they think and dream in.
Which of your languages do you count in?
Why ask it
People who speak three languages often count, swear and do arithmetic in only one, and it is not always their strongest. The answer says something about their earliest schooling that a direct question about language never gets to.
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.
How do people greet each other where you are, and what do visitors get wrong?
Why ask it
This is one of the few culture questions with a genuinely practical answer, since kissing, handshakes and how much distance to leave vary sharply even between neighbouring countries. The mistakes half is what makes it fun to answer rather than a quiz.
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.
What do people where you live think about my country, and what do they get wrong?
Why ask it
Braver than it looks, and usually answered generously. You will hear the version of your country that travels through television and news, which is worth knowing and often uncomfortable.
What do you defend about your country abroad but complain about at home?
Why ask it
The double standard everyone has, and admitting it is more honest than either pride or criticism alone. Watch for the answer that is only praise: it usually means they are still treating you as an outsider to be managed.
If you came here, what would you want to see or do?
Why ask it
Gives you a way to send something useful back, whether that is a photograph, a leaflet, or a description of somewhere they named. Their list is also a good measure of what they already believe about your country.
What time is it there as you finish this letter, and what do you think I am doing?
Why ask it
The time difference is one of the stranger facts of writing to someone abroad, and guessing at the other person's hour makes it concrete. Their guess also shows how well they have pictured your day from what you wrote.
What do you watch or read that comes from my country, and is it dubbed, subtitled or translated?
Why ask it
It tells you which version of your country reaches them, and through what filter. Titles often change completely in translation, so ask what a film you both know is called there.
How do you write the date and your address, and what does each line of the address mean?
Why ask it
Day and month swap places between countries, and an address can run from the country down to the door or the other way round. Knowing the pattern saves a misread birthday and helps you copy the envelope correctly.
Fun
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.
What is a slang word or phrase from your area that would confuse an outsider?
Why ask it
Reliably fun and reliably specific to place, since slang varies between towns as much as between countries. Send a couple of your own back, along with what they literally translate to.
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.
If we swapped lives for one day, which part of mine would you want to try first?
Why ask it
They have to go back through your letters for the detail they liked, so you find out what stuck. Reply with the part of their day you would take, and you each have something new to describe.
What is the silliest thing you have ever got in trouble for?
Why ask it
Small crimes travel well by post: a climbed fence, a borrowed bike, a joke a teacher did not enjoy. Nobody has to be brave to answer it, which is why it suits a second or third letter.
Can you draw me your pet, your shoes or your breakfast, whichever is nearest?
Why ask it
A drawing is something an envelope can carry that a typed message cannot, and a bad one is funnier than a good one. Offering three subjects means nobody is stuck choosing.
What is the worst present you have ever had to say thank you for?
Why ask it
Everyone has one, and the story of keeping a straight face is the fun part. It also quietly tells you what not to put in a parcel.
Which snack would you defend against anyone, and what does it taste like?
Why ask it
Describing a taste to someone who cannot buy the thing is harder than it sounds, and the attempts are usually comic. Send your own in return and see whether either description holds up if one of you ever tries it.
If your pet, or the nearest animal, could write to me, what would it complain about?
Why ask it
It lets someone be silly on paper without having to joke about themselves. Shy writers often manage a whole page in the voice of the cat.
What game did you play as a child that had rules only your street understood?
Why ask it
Street games pick up local names and house rules, so comparing them shows how much is shared and how much is not. Ask for the rules written out well enough that you could play it.
Would you rather get one very long letter twice a year or a postcard every week?
Why ask it
A would-you-rather with a real use, since the answer tells you what sort of post they enjoy opening. Most people defend their choice at length.
What nickname do you have, and who is still allowed to use it?
Why ask it
Nicknames come with an origin and a short list of permitted users, and both are fun to tell. Do not start using it yourself unless they offer.
Deeper
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.
What is the longest journey you have taken, and where were you going?
Why ask it
Works for someone who has crossed an ocean and for someone who has never left their region, which is why the wording avoids the word travel. The reason for the trip is usually more interesting than the destination.
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 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 is the last thing you made with your hands?
Why ask it
This puts a floor under letters that have drifted into opinions and general talk. It often produces something that can be photographed or posted, which is how a paper correspondence builds up its own history.
What did you believe strongly at sixteen that you no longer believe?
Why ask it
Easier to answer than a direct question about current beliefs, which makes people defensive. What someone dropped shows the shape of a change they went through, and the way they tell it shows whether they have made peace with it.
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 are you slowly working towards that people around you do not know about?
Why ask it
Distance is the asset here. Correspondents will describe a plan to someone in another country that they keep from everyone nearby, precisely because you cannot repeat it to anyone whose opinion would cost them anything.
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.
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.
Our letters
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.
What surprised you most in my last letter?
Why ask it
Turns the exchange into a conversation rather than two parallel monologues. It also shows you which of your ordinary details are the interesting ones, which is hard to guess from your own side.
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 do you want to ask me but worry might be rude?
Why ask it
Penpals frequently sit on questions about religion, money, weight, guns or family arrangements for months. Inviting them explicitly is the only reliable way to get past the polite phase, and you should be ready to answer plainly.
How many people are you writing to, and what makes a correspondence last for you?
Why ask it
Worth knowing whether you are one of two or one of thirty, since it explains reply times without anyone taking offence. The second half tells you what they will actually keep up with: long letters, short ones, photographs, or a steady rhythm above all.
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.
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
Asked early, questions about what your people think put someone in the position of speaking for millions. Start with their street, their family and their week, and keep the questions about each other's countries for later letters.
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.