Hold My LetterVol. XIV · Spring MMXXVI
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An Open When Letter

Open When It's Our Anniversary

The letter from earlier in the marriage, arriving on the right day.

An anniversary letter you wrote a year ago and forgot about is the most powerful kind. It catches you off-guard on the morning of, before the dinner reservation, before the gift, before the obligatory text from your in-laws.

Write the letter on a Tuesday morning when nothing is happening, while the love is unprompted. We mail it on your anniversary — first, fifth, twentieth. The version of you who wrote it is gone by the time the letter arrives. The version reading it is who needs it.

Write an Open-When Letter — $19

Suggested Prompts

What to put inside

Pick one or two. The letter does not need to cover everything. It just needs to be specific.

  • The unimportant thing they did this week that you are trying to remember
  • What you would not give up about your marriage to fix what is hard about it
  • A specific reason you would say yes again
  • Something you have never said out loud about how they show up for you
  • The line you would put on their tombstone in fifty years (write it now while you can be light about it)

Simple Pricing

One payment. No subscription.

$9 digital or $19 handwritten — both arrive sealed on your chosen date.

Digital Future Letter

$9

Type online. We print, seal with wax, mail on your date.

Mail-in Handwritten

$19

Handwrite by hand. We store sealed, mail on your date.

Frequently Asked

The short version

What is an open-when letter?

A sealed letter labeled with the moment it should be opened — “Open when you miss me”, “Open when you can't sleep”. The tradition started in military families; the format is now used by everyone in any long-distance or high-stress relationship.

How does delivery work?

You write the letter (digital $9 or handwritten $19), pick a future date one month to two years out, and we mail it on the morning of that date. Real envelope, real wax seal, US mail.

Should we both write one?

Yes. The most-loved version of this tradition is each partner writing on their wedding day or anniversary, both letters held by us, both delivered the same day a year (or two) later, opened together.

What is the longest window?

Two years. So a wedding-day letter for the second anniversary, an anniversary letter for the next one. Beyond two years is on our list but not built yet.

Other Open When Letters

Ready to write yours?

Write Digital — $9Handwritten — $19
Write Your Letter