You have matched with someone on the other side of the world. The page is blank. You have typed "Hi! How are you?" and deleted it twice.
This is the hardest letter you will ever write to this person, and it is hard for a reason that has nothing to do with you: you are trying to be interesting to a stranger while knowing nothing about them. Every letter after this one is easier, because they will have given you something to respond to.
Here is how to get past it.
How long should a first letter be?
About one page. Roughly 200 to 250 words.
That is not a stylistic preference. It is the number that gets answered.
A three-line message reads as a test — are you real, will you reply — and puts the whole burden of starting the conversation on someone who owes you nothing. A three-thousand-word autobiography is worse: it arrives as homework. The person on the other end has to match your effort or feel rude, and the easiest way to avoid that decision is to never open it.
In Letterway a first letter is capped at 220 words and 1,200 characters, on both sides — you get one short letter, and so do they. The cap lifts once you have each written one. It is one of the few rules in the app that people push back on before they use it and defend afterwards, because a limit removes the question of how much is too much.
If you are writing on paper, one side of A4 in normal handwriting is almost exactly this.
Two caps, not one, because word counts do not travel. A word counter splits on spaces, so four hundred Japanese characters can count as a single "word" while filling four pages. A character limit is the one that means the same thing in every language.
The first line
Skip "Hi, how are you?" Not because it is wrong, but because it is the line they will read at the top of every letter they receive that week.
Three openings that work, in rough order of how well:
1. Name the thing that made you pick them.
I saw you write about long-distance running and living somewhere it snows for five months, and I wanted to know how those two facts get along.
This does an enormous amount at once. It proves you read their profile, it is specific enough that they cannot reply with a stock answer, and it hands them an easy first sentence.
2. Start in the middle of something.
It is 11pm here and there is a wedding two streets over, so this letter is being written to drums.
Where you are, right now, in a way nobody else could have written. It makes you a person immediately rather than a profile.
3. Say the honest thing.
This is my first letter to a stranger in about fifteen years and I have rewritten this line four times.
Slightly risky, disarming when it lands, and it gives them permission to be awkward too.
What all three have in common: they are not about you being interesting. They are about giving the other person something to hold.
What to actually write about
The instinct is to summarise yourself — age, job, city, hobbies, done. Resist it. A summary is a list of nouns, and nobody can reply to a noun.
Write about one thing, in detail, instead of five things in passing.
Bad, because there is nothing to answer:
I like cooking, reading and hiking. I work in accounting. I have a cat.
Better, because every sentence is a door:
I have been trying to make my grandmother's rice for two years and it is never right. She refuses to write the recipe down — she says you learn it by standing next to someone — so I am basically reverse-engineering a dish from memory and phone calls. Last week I got the smell right and the texture wrong, which felt like progress.
That is the same person. The second version can be replied to in nine different ways: their own grandmother, their own failures, what food means where they live, whether they think recipes should be written down at all.
Good subjects for a first letter, because everyone has one and nobody's is the same:
- Something you are bad at and doing anyway
- What is directly outside your window
- A small thing that is normal where you live and strange everywhere else
- Something you changed your mind about recently
- What you were like at fourteen
- A thing you keep meaning to do
Questions to ask a pen pal
Ask one or two. Not a list.
A first letter with eight questions turns into an interview, and interviews get answered once and then abandoned. One good question gets answered properly and gives you the next letter for free.
The best questions are ones where the answer cannot be looked up:
- What is the sound you associate most with where you grew up?
- What does an ordinary Tuesday look like for you?
- Is there something everyone in your country knows that outsiders always get wrong?
- What did you believe as a child that you were very sure about?
- What is the last thing you made with your hands?
- What is something you're supposed to like and don't?
Avoid the ones that sound conversational but only have one answer — what are your hobbies, what music do you like, what do you do for work. They will answer them, politely, and neither of you will have anything to say next.
Ask the question at the end, not the middle. It is the last thing they read before they start writing back.
What not to write in a first letter
Six things that reliably end a correspondence before it begins:
- The résumé. Age, job, relationship status, five hobbies. It reads like a form.
- Too many questions. See above — it becomes an interview.
- Heavy personal disclosure. Grief, illness, loneliness. These belong in a correspondence, and this is not one yet. Save it for letter four, when it will land instead of alarm.
- Romance. If they wanted that they would be on a different app. It is the fastest way to be blocked.
- Anything you would not want a stranger to have. No address, no phone number, no workplace, no school, no full name until you have decided you want to.
- "Sorry this is boring." You are telling them what to think before they have decided. Delete the apology and the letter is instantly better.
How to end it
Two sentences, not a paragraph.
A forward look — I hope this reaches you on a good day — and then your name. That is genuinely all it needs. A long sign-off is usually anxiety wearing a hat.
If you want to make replying easier, end on the question. Give them the last word to answer rather than a summary to acknowledge.
A full example you can borrow
Here is a complete first letter. It is 198 words, which is roughly the shape you want.
Dear Ines,
I picked you out of the list because your profile said you fix bicycles and cannot ride one. I have read that sentence about six times and I still want to know how it happened.
I am writing from Charsadda, in the north of Pakistan, at the hour of the evening when everyone's cooking arrives through the windows at once and you can tell what the whole street is having for dinner. Mine is going badly. I have been trying to make my grandmother's rice for two years and it is never right — she will not write the recipe down, she says you learn it by standing next to someone, so I am reverse-engineering a dish out of memory and phone calls. Last week I got the smell right and the texture wrong. I am choosing to call that progress.
I am 27, and I have recently learned that I like doing things badly in public far more than I expected to.
What does an ordinary Tuesday look like where you are? Not a good one. An ordinary one.
I hope this finds you somewhere warm.
— Owais
Notice what it does not do. It does not list hobbies. It asks one question. It gives away nothing that could identify a house. And every single paragraph could be replied to.
What if they don't reply?
Some of them will not, and it will usually not be about your letter.
People sign up to a pen-pal app in a burst of enthusiasm, receive four letters in a week, answer one, and feel too guilty about the other three to open the app again. That is not rejection. That is an inbox problem, and it is one we think about a great deal — we wrote about why being ghosted is partly a design problem.
Two things genuinely improve your odds:
- Write to people whose reply rate you can see. Letterway shows how often someone answers a first letter, and how long they usually take, before you spend an hour writing to them. Somebody who has answered eleven of twelve is a far better bet than somebody new, and you should not have to find that out the hard way.
- Do not send the same letter to ten people. It is obvious from the first paragraph, and the ones worth writing to are exactly the ones who will notice.
Then let it go. A letter you enjoyed writing was not wasted, even if nobody answers it.
The one-line version
Write one page. Open with something only you could have written. Tell one story in detail instead of five in summary. Ask one question they cannot look up. Do not apologise.
Letterway is a pen-pal app where letters take real time to cross real distance — a letter from the next town lands within the hour, one from the other side of the world takes most of a day, and there is no way to pay to make it faster. You can see how often someone replies before you write to them. It is free to write.