How to answer a pen pal letter

Everyone worries about the first letter. Far fewer people think about the reply, and yet the reply is where most pen pal friendships are actually made or lost. A first letter only has to introduce you. A reply has to prove you were listening, keep the conversation moving and leave the other person wanting to write again. This guide is about doing all three without turning your letter into homework.

Read it properly before you write a word

It sounds too obvious to say, but most weak replies come from a letter that was skimmed. You read it on your phone on the bus, you felt pleased, and three days later you sit down to answer it from memory. What you remember is the general shape: they went somewhere, they asked about your job, something about a sister. What you have forgotten is the detail that would have made your reply feel like a conversation.

So read it twice. The first time, just enjoy it. The second time, read it like someone who has to answer it, and notice four things:

• The questions they asked you, including the ones tucked into the middle of a sentence ("I have no idea what people eat for lunch in Scotland, actually").
• The things they told you that clearly matter to them — the parts they wrote at length, or came back to twice.
• Anything that sounded tired, worried, proud or excited. Tone is easy to miss on a first read.
• Anything you did not understand. A word, a reference, a name you do not recognise. These make excellent questions.

Some people jot these down in a short list before they start writing. It takes two minutes and it stops you finishing a reply and then realising you forgot the one thing they really wanted to know.

Answer their questions, but not like a form

Your pen pal asked you things, and the polite and natural thing is to answer them. The trap is answering them in order, one after another, so your letter reads like a completed questionnaire: "1. My favourite food is lasagne. 2. Yes, I have a brother. 3. It is cold here." Every question is answered and the letter is dead.

Instead, fold the answers into whatever you want to say anyway. If they asked what you had for dinner and whether you like your job, those can become one paragraph about a long Thursday at work that ended with beans on toast because you could not face cooking. The questions are answered, but now there is a story, and a story gives them something to reply to.

It also helps to answer with a little more than was asked. "Do you have pets?" can be answered "Yes, a cat", or it can be answered with the cat's name, its worst habit and the time it got stuck behind the fridge. The second answer takes three more sentences and gives your pen pal three more things to ask about.

Respond to what they felt, not only to what they said

Letters carry feelings in a way chat messages often do not, partly because people write them when they have time to think. If your pen pal tells you their grandmother is in hospital, or that they finally passed a driving test on the fourth attempt, the most important part of your reply is how you respond to that — not your news about the weekend.

Put it near the top. A reply that opens with three paragraphs about your holiday and then adds "Sorry to hear about your gran" at the very end reads as though you nearly forgot. Something simple, written first, is enough: "I am really sorry about your grandmother. I hope she is comfortable, and that you are getting some sleep." You do not need to fix anything or offer advice nobody asked for. You need to show you noticed.

Good news deserves the same attention. People are often shy about their own achievements and will mention them in passing. If they slipped "oh, and I got the place at university" into the last line, make a fuss about it in your first. Being properly pleased for someone is one of the quickest ways to become a friend rather than a correspondent.

Add something new of your own

A reply that only answers is a reply that runs out. If every letter is a response to the previous one, the conversation slowly narrows until there is nothing left to respond to. This is a big part of why so many correspondences quietly stop after the third or fourth exchange, something we look at more closely in getting past letter three.

So every reply should bring at least one new thing into the room. It can be small: something that happened this week, a song you cannot stop playing, a strange local news story, a question you have been wondering about since you started writing to them. The rough balance that works for most people is something like half answering and half offering. They should come away knowing something about you that they did not know before.

If you genuinely cannot think of anything, a prompt can help — the letter prompt generator hands you one subject at a time, and there is no shame in using it. Pen pals have been borrowing topics from each other and from newspapers for as long as there have been pen pals.

Pick up threads from earlier letters

Some of the best moments in a long correspondence come from remembering. Three letters ago your pen pal mentioned a job interview; did they get it? In their first letter they said they were trying to grow tomatoes on a balcony; how are the tomatoes? Asking about something they told you weeks ago shows that their letters stay with you after you have answered them, and that is a rare and lovely feeling for the person on the other end.

This is easier if you keep the old letters somewhere you can find them, and look back at the last two or three before you start writing. On PenPalConnect the whole conversation stays in one place, so scrolling back is easy. With paper letters, a shoebox and a habit of rereading are all you need.

Threads also give a correspondence its own private language: the tomatoes become a running joke, the terrible boss a recurring character. For more on keeping the whole thing alive over months and years, see the guide to keeping a pen pal conversation going.

Match their length, roughly

There is no correct length for a reply, but there is a correct relationship between your letter and theirs. If they wrote you a thousand words and you send back a hundred and fifty, it can feel like a brush-off, however warm the hundred and fifty are. If they wrote you a short note and you answer with four pages, it can feel like pressure — as though they now owe you four pages back.

Aim to be in the same neighbourhood: a little shorter or a little longer is fine, wildly different is not. A few exceptions are worth knowing:

• If your pen pal is writing in a second language, a short letter may have taken them an hour. Do not read it as low effort, and think twice before sending them a wall of text.
• If they wrote something long because something big happened, a long reply is welcome even if your letters are usually short.
• If you are going through a busy patch, a short letter that says so ("A quick one, because exams, but I did not want to leave you waiting") is far better than a long silence.

An example: the letter

Say your pen pal, Ines, who lives in Lisbon, sends you this:

Hi Tom,

Thank you for your letter and the photo of the frozen canal — I could not believe people actually skate on it! Here it never gets colder than about eight degrees and everyone still complains.

This week has been strange. My father had a small operation on his knee and he is at home now, very bored and very bad at being looked after. I have been doing most of the cooking, which my brother says is a punishment for everyone. I made bacalhau for the first time on Sunday and it was not terrible.

You said you are studying engineering — what kind? And what do you do to relax when you are not studying? I have started running in the mornings but I am not sure it is relaxing. Also, is it true that in England you put milk in tea? My aunt says yes and I do not believe her.

Beijinhos, Ines

An example: a good reply

Dear Ines,

First, I hope your dad's knee is mending, and that he is being a slightly better patient by the time this reaches you. My grandad had the same operation two years ago and spent the whole recovery trying to walk to the shop before he was allowed to. Good luck to all of you.

Bacalhau on the first attempt is brave. I had to look it up — salt cod, soaked for days? — and I am impressed it was "not terrible", which I think is the highest praise a brother can give. My own cooking peaked this week with a pasta bake that set off the smoke alarm, so you are well ahead.

I study civil engineering, which mostly means bridges, drains and a surprising amount of maths about mud. To relax I play five-a-side football badly on Wednesday nights, and I have just started a pottery class, where I have so far made two bowls and one object nobody can identify. I will send a photo of the mystery object next time.

Your aunt is right, I am afraid. Milk in tea is completely normal here, and people argue seriously about whether it goes in before or after the water. What do people drink in Lisbon in the morning? I am guessing coffee, but I have a feeling there are rules.

And how is the running? Has it become relaxing yet, or is it still a punishment too?

Take care, Tom

Why that reply works

Tom opens with Ines's father, because that was the most important thing in her letter. He picks up her joke about the cooking and adds one of his own. He answers both of her questions, but inside paragraphs about his week rather than as a list, and each answer has a detail she can ask about: the mystery pottery object is practically begging for a follow-up. He settles the tea question and turns it straight back into a question about her mornings. He remembers the running, which she only mentioned in passing, and asks about it at the end.

It is about the same length as her letter. It contains nothing remarkable. It is simply a reply written by someone who read the letter properly, and that is the whole skill. If you want to get better at the question side of things, how to ask better questions goes into more depth.