What to Write to a Pen Pal When You Don't Know What to Say
Part of the Ultimate Guide to Pen Pals
The blank page is the only hard part of having a pen pal, and it’s easier to beat than you think. You don’t need to be interesting. You need to be curious, and a little bit honest. Everything below is a tool for one of those two jobs: a first letter you can copy, the trick to answering the letter already on your desk, twenty questions sorted by depth, and a pocket list of small flat things to slip in the envelope. And if you’re missing the pen pal itself, the ultimate guide to pen pals covers finding one; come back with an address.
What do you write in a first letter to a pen pal?
Introduce yourself in small, true details: your name, your town, what fills your days, one thing you can’t stop thinking about lately. Add two or three questions you’d honestly like answered, keep the whole thing to a page, and close with no pressure to reply fast. A page of true things is enough.
Everyone freezes here anyway. We decide the first letter has to be clever and full and profound, and so we write nothing at all.
Let that go.
A pen pal letter is a conversation that happens to be slow, and it runs on the same fuel as any conversation: real life, plainly told. “The first tomato finally turned red” lands harder than “things are good.” And your boring is somebody else’s exotic: the bus you take, the birds you can hear, what your street sounds like at dinnertime. To a stranger three time zones away, that’s the good stuff.
A first letter you can copy
Steal this one. Fill in the brackets, cross out anything that isn’t you, add whatever is.
Dear [their name],
I’m [your name], writing from [your town], where the sky is currently [doing whatever it’s doing]. This is my first pen pal letter in [a long time / ever], so forgive me if I get the customs wrong. I hear there aren’t any.
A few true things about me: I [what fills your days], I can see [the thing outside your window] from where I’m sitting, and lately I can’t stop thinking about [tiny obsession of the moment]. The best thing that happened to me this week was [small real thing], which tells you roughly what my weeks are like.
I’d love to hear about yours. What does [their town] smell like this time of year? And what’s the one thing you always tell people about yourself, and the one thing you never get to?
No rush on the reply. Slow is the whole point.
Warmly, [your name]
It fits on a page on purpose. One page is plenty, especially early on: a short letter with real details and one good question beats four pages of filler, and it’s a far kinder thing to answer. For the deeper craft, greeting to sign-off, the ultimate guide to writing a letter has the rest.
The easiest letter is a reply
Once letters are flowing, the blank page mostly solves itself. Reread what they sent and respond to it: answer their questions, ask after the things they mentioned, pick up the thread they left dangling. A good letter listens before it talks. Half of what to say is already sitting in the envelope they sent you.
The other half is making your own letter easy to answer. A letter that’s all statements gives your pen pal nothing to grab onto; a letter with one real question in it half-writes their reply for them. There’s a whole craft to this, and how to write a letter worth writing back to walks through it, but the short version fits in one line: share something real, then hand them a door.
20 questions to ask a pen pal, from first letter to a year in
A pen pal friendship deepens by degrees, and your questions should keep pace. Reach for the first group while you’re still strangers, the second once the letters find a rhythm, the third when you’ve earned it.
For the first letter
- What does your town smell like this time of year?
- What’s the view from where you’re sitting right now?
- What’s the best piece of mail you’ve ever received?
- What are you reading, watching, or listening to on repeat?
- What did you eat this week that was worth writing down?
- How did you find your way to pen pals?
- What’s the one thing you always tell people about yourself, and the one thing you never get to?
For the third letter
- What’s a small thing you’re strangely proud of?
- What did you want to be when you were eight?
- What’s a smell that takes you straight back somewhere?
- Walk me through a Saturday at your house.
- What’s something you’ve changed your mind about?
- Who taught you something you still use, and what was it?
- If you could move anywhere tomorrow, where, and what’s stopping you?
For a year in
- What are you afraid of that you’ve never said out loud?
- What do you hope this stretch of your life turns out to be for?
- What’s a memory you’d hand me if you could?
- What would you do with a free month and nobody watching?
- What are you still grieving, if you feel like setting it down on paper?
- What do you know now that you wish someone had written to you ten years ago?
The early letters are weather and hobbies; the later ones, if you let them, become fears and hopes and the things you don’t tell the people you see every day. When a friendship gets that far, protect it: how to keep a pen pal friendship going covers the lulls, the life changes, and the letter after a long silence.
What should you enclose with a pen pal letter?
Enclose flat, light things: stickers, a pressed flower, a photo, a tea bag, a ticket stub, a recipe in your handwriting. Keep the envelope flat and under an ounce and a single Forever stamp usually carries a US letter (82 cents as of the July 2026 rate change); an international letter takes a Global Forever stamp ($1.75).
A letter can carry more than words, and small enclosures turn it into a little parcel of your life. Some favorites:
- A photo of something you mentioned in the letter. Proof the tomato really did turn red.
- Stickers, the unofficial currency of snail mail. Send a few, get a few back.
- A pressed flower or leaf from a place you’d go back to, folded into a square of waxed paper.
- A tea bag, so the two of you can drink the same cup a week apart.
- A ticket stub, a bus transfer, a page from a day planner… any flat scrap that says this is what my life looks like up close.
- A recipe card in your handwriting. Food travels better on paper than you’d think.
- A doodle in the margin. Stick figures count.
One courtesy: skip the glitter. It escapes every envelope ever sealed, and pen pals have long memories about their carpets.
Your next letter
If you already have a pen pal, steal the template, spend the questions slowly, and obey the glitter rule. And for a little company between letters, the Mail Club Hub Monthly is my once-a-month note on all things snail mail.
If you don’t have one yet, that part is the easy part: the pen pal directory gathers the free groups, the postcard exchanges, and the hand-matched services in one place. I catalog it by hand, and there’s a fit in there for whoever you are.
Write the first honest line today.