
Circa 2007, open when letters were made wildly popular when Gerard Butler left them for his grieving wife in the movie ‘P.S. I Love You’. Since then, long-distance girlfriends and military spouses have been sending these adorable letters all over the globe.

Open when letters are a gift to a loved one that have specific instructions on when to open them. They can be used to celebrate special anniversaries, holidays, and events or to encourage, cheer, and reassure them during your time away from each other
These letters are especially useful for service members who can’t receive mail regularly, such as service members on submarines or in remote locations. In these situations, you would give your loved one all the letters before their departure and they can open the letters when the need or special day arrives.
Open when letters can be as simple or elaborate as you like and there are many different themes/types that you can make. You can include gifts, jokes, and pictures or just the letters by themselves. There are a bazillion ways to make each letter unique. It’s hard to even know where to start.

I knew that I wanted to make these letters for my husband while he was overseas as part of my Deployment Bucket List.
Below are the Open When Letters I sent my husband during a 15-month hardship tour and a list of all the things I put in them.
Open It Now

This letter is a must! It explains the ‘rules’ of the letters and gives instructions on when to open them. Thus, it should be opened first.
- rules for the letters
- love letter/sweet note
Open When You’re Sick

This letter was kind of like a mini care package for a sick day. It sucks not being there for your loved one when they are sick, but this is the closest thing you can do to take care of them from far away.
Ludens Deliciously Soothing Throat Drops, Watermelon, 90 Drops Per Bag, 90 CountKleenex 3-Ply Pocket Pack Facial Tissues (32 Pack of 10 Tissues)
SoundHealth Vitamin C Drops, Assorted Citrus Flavor, 140 Count
Open When I’m Mad at You

If you’re in a long-distance relationship (or any relationship), it’s inevitable that you are going to argue. This letter is can serve as a reminder that even though you’re angry now, there is so much more love to be shared in the future.
- long letter
- pictures of us together
- marriage/relationship quotes
- sweet meme
Hallmark American Heroes Thinking of You Card Assortment (10 Cards with Envelopes) (2499RZC1015)DiverseBee 50 Pack Assorted Inspirational Cards – Motivational Kindness Mini Note Cards, Encouragement Mindfulness Affirmation Card Set with 50 Unique Quotes (Business Card Size)
120 Pieces Assorted Motivational Quote Cards Gratitude Encouragement Card Set, 30 Styles Business Cards 2 x 3.5 Inch Mini Inspirational Kindness Note Cards for Encouraging Business Kindness Supplies
Open When You’re Stressed

Living away from family and friends is hard. Add in the strain of a job, school, or combat and stress levels rise exponentially. This letter is a reminder that this, too, shall pass. On the backs of the pictures I tried to put relevant or funny captions.
- “treat yo’self” card with money
- funny memes
- scripture
- encouraging card/letter
- pictures of loved one with funny captions
- piece of bubble wrap
Central 23 – Funny Birthday Card –Patriotic Blank All Occasion Greeting Cards / 24 American Flag Note Cards With White Envelopes/USA Military 4 7/8
Duck Brand Bubble Wrap Roll, Original Bubble Cushioning, 12
Open When You Need a Confidence Boost

Some days you just aren’t ‘feeling yourself’, which is where this letter comes in. It’s a great way to remind your loved one of all of their best qualities. The little book of ‘Why You’re So Awesome’ was probably my husband’s favorite thing in all of the letters. I filled in some of the answers myself, but I let the kids answer most of them, which made it quite comical.
- reassuring card/letter
- diy book about why you’re so awesome
- your favorite picture of your loved one
Knock Knock Why I’m Grateful for You Fill in the Love Book Fill-in-the-Blank Gift JournalStationary Paper and Envelopes Set 48 Pack of Watercolor Letter Writing Paper, Decorative Printer Stationery Sheets Set with Assorted Designs – Double-sided Printing – 8.5 x 11 Inch
Knock Knock Why You’re So Awesome Fill in the Love Book Fill-in-the-Blank Gift Journal
Open When You Are Sad

Being sad is unavoidable when you’re away from the people you love. This letter is an excellent opportunity to cheer up your loved one by reminding them of all your inside jokes and fun times.
- whoopee cushion
- funny meme
- “treat yo’self” coupon with money
- encouraging card/letter
- illustrated list of things to do when you’re sad
The Dreidel Company Large Original Mondo Whoopee Cushion 10Andaz Press Funny Jumbo Birthday Card With Envelope 8.5 x 11 inch, Greeting Card, Treat Yo’Self
Deeplay Motivational Encouragement Greeting Cards, 24 Packs Holographic Inspirational Quote Cards, Thinking of You, Appreciation and Kindness Cards for Colleagues, Classmates, Family and Friend, with 24 Envelopes and Stickers
Open When You Are REALLY Bored

Boredom is the worst when you’re away from family and friends. It’s a terrible reminder of how lonely you are. This letter is a chance to try something new and maybe learn a little bit about each other while you’re at it.
- relationship questions
- relationship crossword puzzle
- funny memes
- word search, Sudoku, maze, etc.
- deck of cards
Quick And Dirty: Military – Fast, Fun, Comedy Game by Disgruntled DecksDisgruntled Decks – The Original Military Party Card Game for Veterans – Army-Themed Deck
Sudoku Pocket: Compact Size, Travel-Friendly Book with 200 Easy to Medium Sudoku Puzzles and Solutions
Open When You Miss Me

Missing your loved one sucks, but it sucks even more to know that they are missing you and there’s nothing you can do about it. This letter is a good way to remind your loved one of just how much you love them and miss them too.
- sweet quote
- sweet, but funny meme
- pictures of yourself
- love letter/sweet card
Iconikal 24-Photo Clear Cover 4×6 Photo Album, 5-Pack79 Vintage Stationary Paper and Envelopes Set Includes 30 Sheets Antique Letter Papers with 3 Sizes, 12 Kraft Envelopes, 12 Retro Keys, 12 Hemp Rope and 12 Stickers for Christmas Handmade Letter
IMagicoo 32 Lovely Cute Writing Stationery Paper Letter Set with 16 Envelope + 1 Sheet Label Seal Sticker (Style-11(8.3×5.8))
Open When You Miss the Kids


Being away from your children and missing out on part of their lives is heart-breaking. These letters (I did one for each kid) are an uplifting way to remind your loved one that their children haven’t forgotten about them and they are missing their daddy/mommy too.
- card/letter from child
- pictures of child with daddy/mommy
- drawings from child
- small trinket or candy that child picked out
Wallniture Barre Wire Picture Hangers for Kids Crafts and Artwork, Expandable 196 Inch Wall Decor with 24 Clips Set, SilverGirlZone Unicorn Letter Writing Set For Girls, 45 Piece Stationery Set, Great Birthday Gift for Girls of All Ages
24 Pcs Letter Writing Stationery Paper Set Woodland Animal Design Greeting Cards with Envelopes for Kids Classroom Birthday Party
Open When You’re Jealous of Jody

Only military couples will understand the title of this letter, but it’s basically a letter for when your significant other is afraid that you will leave them for someone else while they are gone. This letter is a perfect opportunity to reassure your loved one that they are the only one for you.
- inappropriate, but funny memes
- pictures of us together
- reassuring card/letter
Open When You Have Doubts

Doubting ourselves is unavoidable, especially when we’re under pressure. This letter can serve as a reminder for all of your loved one’s admirable qualities and serve as encouragement for whatever stressful situation they are facing.
- encouraging card/letter
- sweet quote/song lyric
- picture with funny caption
Open When Time Has Slowed Down

During a deployment, time will slow to an absolute crawl. This letter reminds your loved one that this season of their life WILL eventually end and they WILL be home again.
- scripture
- “treat yo’self” coupon with money
- encouraging card/letter
- funny picture
Religious Motivational Quote Cards/Business Card Size / 50 Positivity CardsJoe Biden Inspired Parody Card Treat Yo’ Self Birthday Celebration Congrats Card 5×7 inches w/Envelope
Bob Ross Bobblehead: With Sound! (RP Minis)
I sent these open when letters to my husband as one of his monthly care packages while he was gone. (You can see all of the care packages I sent him here!)
I hope these ideas inspire you to get started on your own open when letters. They are a lot of work, but I’m sure that your loved one will enjoy them as much as my husband did!






