36 envelopes to choose from

Open when…

A stack of sealed letters, each one for a moment that hasn’t happened yet. Say who they’re for, deal a set, and take a first line for any envelope you get stuck on.

Prints a sheet of cut-out labels, one per envelope. Nothing you choose is saved or sent anywhere.

What goes inside each one

One memory

Specific enough that only the two of you, or only you, would know it.

One true thing

Something about the reader that stays true on their worst day.

One small step

Something doable in ten minutes. Make tea. Go outside. Call someone.

The date

So whoever opens it knows how long the words have been waiting.

Half a page is plenty. Write the label first and the letter second: knowing the moment tells you what to say.

Every envelope, by who it’s for

Open when letters for yourself

Letters you seal now and open later, in your own words.

Open when you can’t sleep
Open when you’re doubting yourself
Open when you’re waiting on news
Open when you’re starting over
Open when something finally went right
Open when you miss home
Open when you’ve had a terrible day
Open when you feel behind everyone else
Open when you’re about to do something scary
Open when you get the answer, either way
Open when it’s your birthday
Open when you can’t decide
Open when you’re lonely
Open when you want to quit
Open when it’s raining and you have nowhere to be
Open when you need to remember how far you’ve come
Open when you’ve made a mistake
Open when you’re proud of yourself
Open when you need a reason to get up
Open when it’s the first night in the new place
Open when you’re overwhelmed
Open when it’s been a year
Open when you’ve forgotten why you started
Open when you need to forgive yourself
Open when it’s New Year’s Eve
Open when nothing is wrong and you just want a letter

Open when letters for a partner

Anniversaries, long days, and the occasional argument.

Open when you can’t sleep
Open when you’re doubting yourself
Open when you’re waiting on news
Open when something finally went right
Open when you miss me
Open when you’ve had a terrible day
Open when you need a laugh
Open when you’re angry at me
Open when you’re about to do something scary
Open when it’s your birthday
Open when you’re sick in bed
Open when it’s raining and you have nowhere to be
Open when you need to remember how far you’ve come
Open when you’ve made a mistake
Open when it’s our anniversary
Open when we’ve had a fight
Open when you’re overwhelmed
Open when you need to hear you’re loved
Open when it’s been a year
Open when you’re bored
Open when it’s New Year’s Eve
Open when you want to call but it’s too late
Open when nothing is wrong and you just want a letter

Open when letters for a friend

For a birthday, a move, or a hard stretch.

Open when you can’t sleep
Open when you’re doubting yourself
Open when you’re waiting on news
Open when you’re starting over
Open when something finally went right
Open when you miss me
Open when you’ve had a terrible day
Open when you need a laugh
Open when you feel behind everyone else
Open when you’re about to do something scary
Open when you get the answer, either way
Open when it’s your birthday
Open when you’re sick in bed
Open when you can’t decide
Open when you’re lonely
Open when you want to quit
Open when it’s raining and you have nowhere to be
Open when you need to remember how far you’ve come
Open when you’ve made a mistake
Open when you’re proud of yourself
Open when you’re overwhelmed
Open when you need to hear you’re loved
Open when you’re bored
Open when it’s New Year’s Eve
Open when nothing is wrong and you just want a letter

Open when letters for someone going away

College, a deployment, a long-distance stretch, a new city.

Open when you can’t sleep
Open when you’re doubting yourself
Open when something finally went right
Open when you miss me
Open when you miss home
Open when you’ve had a terrible day
Open when you need a laugh
Open when you’re about to do something scary
Open when you get the answer, either way
Open when it’s your birthday
Open when you’re sick in bed
Open when you’re lonely
Open when you’re proud of yourself
Open when it’s the first night in the new place
Open when you’re overwhelmed
Open when you need to hear you’re loved
Open when it’s been a year
Open when you’re bored
Open when you’re packing to come home
Open when you want to call but it’s too late
Open when nothing is wrong and you just want a letter

For the ones addressed to you

A shelf of sealed envelopes on your phone.

Dear You is a private journal app for iPhone with an Open When shelf: sealed envelopes for real moments such as can’t sleep, doubting yourself, waiting on news, starting over and something finally went right. Open the right one when the moment arrives, and seal envelopes of your own in your own words.

You can also write a letter to your future self and seal it for a week, a month, a year, three years or five. It stays locked until its day.

Get Dear You on the App Store

Free to start: two Open When letters, one future letter waiting at a time, write-back notes, Face ID lock and PDF export. The full Open When shelf and unlimited future letters are part of Dear You Plus, a subscription. No account, no ads. Requires iOS 17 or later. Details checked against the App Store listing on November 10, 2026.

Publisher disclosure: Honest Little Apps publishes both Dear You and this page. This is not an independent review. This generator is a separate web companion; its envelopes and first lines are not taken from the app. Dear You is a reflection and writing app, not a medical or mental-health service.

Dear You App Store screenshot showing the Open When shelf of sealed envelopes — App Store screenshot from Dear You.

Questions people ask

What are open when letters?

A set of sealed envelopes, each labelled with the moment it should be opened: “Open when you can’t sleep”, “Open when you miss home”. You write them all at once and the other person, or a later you, opens each one when that moment arrives.

How many open when letters should I write?

Six is enough for a card-sized gift, twelve gives roughly one a month, and twenty suits a long stretch apart such as a year away. A smaller set where every letter is specific beats a big set of filler.

Can I write open when letters to myself?

Yes. Seal them on a good day for the days you’ll need them: when you’re doubting yourself, when you want to quit, when something finally goes right. Write in the second person, “you”, as if to a friend.

What do you put inside an open when letter?

Keep it short: one specific memory, one true thing about the person, and one small thing to do next. Add the date you wrote it. A photo, a tea bag or a ticket stub is a nice extra, but the words are the point.

Making a set with someone?

Share the public page. Your chosen envelopes are not included.

Open the public link