How to Write Open When Letters

How many Open When letters to write

Four to six is the right size for a first set. Enough that the right letter exists when they need it, few enough that each one still feels like an event. A stack of thirty written in one sitting tends to blur: by letter twelve you are repeating yourself, and they can tell.

If you want a bigger set, write it over a week or two. Five letters on five different evenings will sound like five letters. Thirty in one night will sound like one letter cut into pieces.

How to pick the moments

Start with the feelings you can predict. You know roughly what is coming for them: the first night somewhere new, missing you, a bad day, a night they can't sleep, a big thing they are nervous about. Those are the letters that get opened, so write them first.

Then add one for joy. A letter for when something good happens and you aren't there to hear about it is the one people forget, and often the one they remember most.

Keep each moment narrow. "Open when you're sad" is fine. "Open when you've had a bad day at work and you don't want to talk about it" is better, because you can write straight at it.

1. Open when you miss meThe one everyone writes first, and the one that gets opened most.
2. Open when you can't sleepWrite it slow and a little boring on purpose, so they can drift off.
3. Open when you've had a bad dayThey don't need a fix. They need to hear that you're on their side.
4. Open the night before something bigAn exam, an interview, a flight, a first day. You know the date, so it lands exactly right.
5. Open when you doubt yourselfA list of things you have watched them do. Evidence beats encouragement.
6. Open when something amazing happens and I'm not thereThe joy letter. Tell them how you would celebrate if you were in the room.

What to write in an Open When letter: a five-part method

Every good Open When letter does the same few things in roughly the same order. You don't need all five every time, but if a letter feels flat, one of these is usually missing.

1. 1. Name the momentStart by meeting them where they are. "If you're reading this, you can't sleep again." One line that shows you knew this moment would come and you thought about it ahead of time.
2. 2. One specific memoryNot "all our good times". One: the jacket at the gate, the song in the car, the night the power went out. A detail only the two of you would recognise does more than a paragraph of forever.
3. 3. What you'd say if you were therePicture yourself sitting next to them in that exact moment. What would you actually say? Write that, in the words you'd use out loud, not the words you'd put in a card.
4. 4. One small thing to do nowGive them something to do in the next ten minutes: drink some water, put this song on, text your sister, go to bed. A letter that ends with an action helps more than one that ends with a feeling.
5. 5. A sign-off that sounds like youUse the name you actually call each other. Say where you were and when you wrote it. Months later, that line about sitting on the kitchen floor at midnight is the part they reread.

Open When letter examples

Two short examples written with the method above. Borrow the shape, not the words. Yours should have details nobody else could write.

1. Open when you miss meHi you. If you're reading this, it's one of those evenings where the flat is too quiet and you keep reaching for your phone to tell me something. I know, because I'm doing the same thing as I write this. I keep thinking about the morning at the train station when you missed the first train on purpose and we got pastries instead. You had sugar on your coat all day and didn't notice. If I were there right now I'd put the kettle on and make you tell me the most boring part of your day, in detail. So here's the plan: make tea, put on the playlist from the car, and send me one photo of whatever is in front of you. I'll know what it means. Written on the kitchen floor at midnight, missing you already. Me.
2. Open the night before your examOkay. Tomorrow is the exam, and right now you're convinced you know nothing. You said exactly the same thing before your driving test, and you passed first time while I was still in the car park eating crisps. You work best when you think you're behind. I've watched it happen for six years. If I were there, I'd take your notes away at ten and make you watch something stupid. So that's what you're doing: close the book, set two alarms, eat something that isn't toast. Whatever happens tomorrow, I'm proud of how hard you worked for it, and that part is already done. Call me after. Love, your biggest fan, writing this from the library on a Tuesday.

Openings that work

The first line decides whether the letter feels written for this moment or just written. These openings work because each one names the moment and puts you in it.

1. "If you're reading this, it's late and you can't sleep."
2. "I wrote this on a Sunday in March, sitting where you're probably sitting now."
3. "You don't have to be okay today. You just have to read this."
4. "I knew this one would get opened first."
5. "Before you read anything else: I'm on your side."

Closings that work

End on something they can hold onto or do. A good closing either gives them a next step or tells them when they'll hear from you again.

1. "Now go to bed. That's an order."
2. "Call me when you're ready. Not before."
3. "Put this back in the envelope. You might need it again."
4. "Same time next week, same terrible jokes."
5. "Written in the kitchen, thinking about you, as usual."

Mistakes to avoid

1. Lines anyone could have written"You mean the world to me" is true, and it's on every greeting card in the shop. If a sentence would fit in someone else's letter, swap it for a detail that only fits in yours.
2. Promises you can't keep"I'll always answer the phone" or "I'll be there next month" can turn into a sore spot if life gets in the way. Write what's true now and what you hope for, and say which is which.
3. Countdowns that may turn out wrong"Only 47 days until I see you" reads badly if the date moves. If you mention a number, frame it as of writing: "as I write this, it's 47 days".
4. Writing the letter they don't need yetAn "open when you're sad" letter full of jokes can land wrong. Match the tone to the moment. Save the jokes for "open when you need a laugh".
5. Trying to fix everythingA bad-day letter isn't the place for a five-point plan. One kind thing and one small step is enough.

Plan your set: worksheet

Fill this in before you write a single letter. It takes ten minutes and saves you from the blank page later. Print it, or answer the prompts in your notes app.

• Who are these letters for, and what is about to change for them?
• Three moments you already know are coming (dates, trips, exams, first nights):
• Two feelings they're likely to have that you won't be there for:
• One good moment you want to be part of, even from far away:
• A memory only the two of you share, to use in one of the letters:
• Something you've watched them do that they don't give themselves credit for:
• A song, place or smell that means "us":
• What you'd say in the first ten seconds if you walked into the room right now:
• The name you actually call them, and how you usually sign off:
• Which letter they should open first, and which one goes at the back:

The PDF has space to write under each prompt.

Before you seal it

Read each letter once more, out loud if you can, and check these.

1. The moment is named on the envelope and in the first line.
2. There is at least one detail nobody else could have written.
3. There are no promises or dates you aren't sure of.
4. It ends with something to do or something to hold onto.
5. It sounds like you talking, not like a card.

Want more prompts?

This guide covers the method and a first set. If you'd rather work from a full stack, the Open When workbook is a paid printable with 60 prompts, planning worksheets and example letters for different people and moments. You don't need it to start. A pen, the worksheet above and one evening is enough.

Questions people ask