Most people’s first experience with Open When letters is probably the movie "P.S. I Love You" starring Gerard Butler and Hilary Swank. The story was about a husband who left letters for his wife to open after his death. However, Open When letters can be used for a lot of things. You can use them to build lasting relationships (especially long distance ones), solidify friendships, keep family close and strengthen marriages. A stack of these letters also make wonderful and inexpensive gifts for anyone with a little creativity and forethought.

How Do Open When Letters Work?

Open When letters work by giving someone a series of letters with instructions for opening at a later date or time. They can be as general as “when you miss me”, “when you’re feeling blue”, or more specific like “for your birthday” or “when you graduate college”.  Ideas and themes can be as creative as you like—the more specific to the individual (including favorite jokes, movies, TV shows and other shared memories) the better.

Open When Letter Rules

Every set of letters needs a first letter to get the ball rolling. This is called the “Open First” letter. In this letter, you should include the rules of the game, so to speak. You can use any rules you like, but suggested ones are:

  • Only open 1 (or 2) per week (to avoid them being all opened at once and losing their effect).
  • Don’t peek (that will ruin all the hard work of putting them together).
  • Don’t share with friends (these are meant to be personal).
  • Don’t throw them away (keeping these as mementos is what makes Open When letters so fun and special ).

280 Open When Letter Ideas

There are many different types of Open When letter topics including romantic, inspirational and those saved for important dates. The letters are especially helpful for long-distance relationships, military deployments or keeping in touch with a friend or close relative. Additionally, it’s a great idea for the guy who has a rough time remembering to get a card sent in time—it’s all done in advance! You can surprise someone with the idea, or talk about an Open When letter swap.

Ideas are separated into specific categories here, but many of them can crossover pretty easily, so feel free to pick and choose the one that makes the best sense for your project.

Open When Letters for Long-Distance Relationships

One of the primary reasons for an Open When letter project is that they are a wonderful way to keep the fires burning in long distance relationships, or for when you and a loved one have to be apart for a significant length of time.

OPEN WHEN …

  • you first unpack
  • you miss me
  • you need a kiss
  • you need a hug
  • you miss holding my hand
  • you are on your way to visit me
  • you want to see my face
  • you need a massage
  • you need help falling asleep
  • you need me to be there for you
  • you need my protection
  • you need to see a picture of us
  • you’re thinking about how much you love me
  • we have an argument
  • we just got off the phone
  • you want to tell me something, but I’m not available
  • it’s the anniversary of when we met
  • it’s the anniversary of our first date
  • it’s the anniversary of our engagement
  • it’s the anniversary of our first big trip
  • it’s our wedding anniversary
  • it’s a week after you’ve been gone
  • it’s a month after you’ve been gone
  • it’s a month until we see each other again
  • it’s a week until we see each other again
  • it’s the day before we see each other
  • you’re on your way again after we’ve seen each other
  • you need to read something romantic
  • you think about laying in bed with me
  • you need a cuddle
  • you’re booking our next visit
  • you need to tell me something important
  • you’re worried we won’t make it
  • you’re somewhere beautiful
  • you visit our favorite place
  • you don’t know what to write to me
  • you feel naughty
  • you need to feel loved
  • you need to tell me you love me
  • you’re afraid we’re drifting apart

Open When Letters for Encouragement

Encouragement letters are simple ways to keep people going in rough times. Give these to a friend, a child or even to your future self!

OPEN WHEN …

  • you have a bad day
  • your faith starts to waiver
  • you feel nervous about a big event
  • you’re angry at everything
  • you need a laugh
  • you need to hear a friendly voice
  • you can’t take it anymore
  • you’re too tired to get out of bed
  • you have a cold
  • your allergies are flaring up
  • you have a nightmare
  • you’re sick to your stomach
  • you think the world is against you
  • you don’t like what you see in the mirror
  • you’re worn out
  • you think you didn’t do the right thing
  • you need to make a big decision
  • you need inspiration
  • you need a pep talk
  • you lose your job
  • you get a promotion
  • you get a bad grade/evaluation
  • you miss your friends
  • you’re scared at night
  • you start to question a big decision
  • you have a big life question
  • you’re in the hospital
  • someone you know is in the hospital
  • I’m in the hospital or sick
  • you’ve had a streak of bad luck
  • you are somewhere that seems hard to get away from
  • you’re feeling small
  • you’re blue
  • you’re crying
  • someone has let you down
  • you missed something important
  • something came collapsing down around you
  • you’re stressed
  • you don’t feel respected by your co-workers

Open When Letters to Commemorate Events

Personal celebrations and holidays are obvious ideas for these Open When cards. Picking obscure dates like “Arbor Day” or “National Talk Like a Pirate Day” can also keep them exciting and fun.

OPEN WHEN …

  • it’s your birthday
  • it’s my birthday
  • it’s your half-birthday
  • it’s your first day of work
  • you’ve finished a great book
  • you get your first paycheck
  • you make a friend
  • it’s Easter
  • it’s Passover
  • it’s Arbor Day
  • it’s Flag Day
  • it’s Canada Day
  • it’s baseball opening day for a favorite team
  • it’s the All Star Game
  • it’s basketball opening day for a favorite team
  • it’s football opening day for a favorite team
  • it’s hockey opening day for a favorite team
  • it’s the first day of the Olympics
  • it’s the Super Bowl
  • it’s Christmas
  • it’s half-way to Christmas (Leon day – June 25)
  • it’s Thanksgiving
  • it’s Mother’s Day
  • it’s Father’s Day
  • it’s Grandparents Day
  • it’s Valentine’s Day
  • it’s St. Patrick’s Day
  • it’s Mardi Gras
  • it’s Cinco De Mayo
  • it’s Pi Day (March 14 – 3.14)
  • it’s International Talk Like a Pirate Day (September 17)
  • it’s Star Wars Day (May 4th – may the 4th be with you)
  • it’s Boxing Day
  • it’s National Jelly Bean Day (April 22)
  • it’s Festivus (December 23)
  • it’s Memorial Day
  • it’s Labor Day
  • it’s MLK Day
  • it’s Independence Day
  • it’s Presidents Day
  • it’s Halloween
  • it’s Earth Day
  • it’s Leap Day
  • it’s Administrative Professionals Day (last Wednesday of April)
  • it’s Groundhog Day
  • it’s the first day of Spring (or when it feels like Spring)
  • it’s the first day of Summer (or when it feels like Summer)
  • it’s the first day of Fall (or when it feels like Fall)
  • it’s the first day of Winter (or when it feels like Winter)
  • it’s the first snowfall
  • you first notice the leaves are changing color
  • you feel like building a fire
  • you feel like you need to cool off
  • it’s really hot out
  • it first gets below zero

Open When Letters for Military Families

It’s not always easy to stay in touch with loved ones in the military especially with those deployed overseas. These ideas don’t just apply to military members per se, but are ideas that generally pertain to brave men and women who are risking their lives to defend our country.

OPEN WHEN …

  • you’ve just been deployed
  • you’ve been deployed a week
  • you’ve been deployed a month
  • you need strength
  • you miss the USA
  • you need to remember how proud I am of you
  • the food isn’t good
  • you’ve hit a wall
  • everything seems foreign to you
  • you need to feel up to an important task
  • you are wondering about something asked of you
  • you need to escape
  • you need a little something from home
  • you feel like hitting someone
  • you feel wrung out
  • you want to talk to me, but can’t
  • it’s Veteran’s Day
  • you’re going on your first mission
  • you’re going on a dangerous mission
  • you get back from doing something risky
  • you don’t feel safe
  • you’re flooded with relief

Open When Letters to Your Children

Anyone who has kids always says the same thing, “it goes by so fast”. Even though you can’t be with them every single moment, there are always opportunities to reach out and support them. An Open When project can offer advice and encouragement for them when you can’t be there.

OPEN WHEN …

  • it’s your graduation
  • it’s your first day of college
  • you have your first big exam
  • before your first big presentation
  • you are homesick
  • you need a little extra cash
  • you’re going to a great party
  • you need a little parental advice
  • you meet someone you love
  • it’s the first day of Freshman Year
  • it’s the last day of Senior year
  • it’s your first big breakup
  • it’s your college graduation
  • it’s your first professional job
  • you get your first promotion
  • you get your first car
  • you do something you regret
  • you have a headache (hangover?)
  • you move for the first time
  • you move for the second time
  • you move in with someone
  • you are thinking about proposing
  • you get engaged
  • you register for your wedding
  • wedding planning is making you crazy
  • you get married
  • you find out you are going to have a baby
  • you have your first child
  • your kid is driving you crazy
  • you have your second child
  • the kid(s) just won’t stop crying
  • you get your first pet
  • your bankroll is getting tight
  • your child goes to kindergarten
  • you have your 10-year High School Reunion
  • you want to know more about where you came from
  • a grandparent passes away
  • you’ve reached a crossroads
  • you wonder what you are doing with your life
  • you need someone to believe in you

Open When Letters for Siblings and Friends

When a good friend or a sibling moves away it can be hard to find the right words in the moment. Packing them some motivational and inspirational letters is a great way to show people that you love them, even when you live far way.

OPEN WHEN …

  • you’re mad at me
  • you’re mad at Mom or Dad
  • you wonder what I’m doing right now
  • you forget something important in my life
  • I forget something important in your life
  • we haven’t talked in long time
  • you feel like I’m not helping
  • something breaks
  • you lose something important
  • you splurge on something that’s too expensive
  • you get a great deal
  • you remember something from our childhood
  • you can’t remember something from our childhood
  • you go on a vacation (without me!?)
  • we make plans to see each other
  • something bad happens to Mom or Dad
  • a childhood home is sold
  • you need something comforting from when you were a kid
  • you need a night out with me, but I’m not there
  • you feel like coming home
  • you feel like NOT coming home
  • you need something that reminds you of home
  • (girls/guys) are jerks
  • you get great news
  • you remember our favorite movie
  • you remember our favorite song
  • you remember our favorite game
  • you think of our friend _____
  • you think of our enemy _____
  • you think of my first love interest
  • you think of your first love interest
  • you need something from your teenage self
  • it’s just Friday
  • you thought about calling me, but something distracted you and now it’s too late
  • you need a cup of tea
  • your power goes out
  • you can’t find something
  • you want to scream
  • you’re trying to diet
  • you’ve ignored my advice

Fun Open When Letter Ideas

Here are some outside-of-the-box, whimsical and weird ideas to riff from that can apply to most of the categories above. They can be for just about any feeling or day and are meant to make someone laugh. Include fun objects to go along with the theme.

OPEN WHEN …

  • you’re feeling really hungry
  • you want to laugh
  • you need something to read in the bathroom
  • you need a backup plan for a rainy day
  • you’re stuck in traffic (or on the train/bus)
  • you need a break from the Internet
  • just for the heck of it
  • you need a silly postcard
  • your refrigerator magnet collection seems sparse
  • you need an instant party
  • you need something mysterious
  • you’re out of underwear
  • you need a new motto
  • you need a new look
  • you need something from the 70s
  • you haven’t shaved for a few days
  • you need to complain
  • you need to rant
  • you want to sing
  • you want to dance
  • you need some sugar
  • you feel fancy
  • you feel sassy
  • you feel gross
  • you can’t figure out what to eat for lunch
  • you need change for the meter
  • clowns are scary
  • you feel wicked
  • you want to make a wish
  • you need a little spice in your life
  • you want to have a little fun
  • you’ve finished a terrible movie
  • you’ve finished a terrible book
  • you’ve eaten something disgusting
  • you’ve eaten something that’s your new favorite food
  • there’s a song stuck in your head
  • you need something to write with
  • you win a bet
  • your feet hurt
  • you smell something funny
  • you need to pull off a death-defying feat
  • you are scared of something ridiculous
  • you forgot to plug in your phone
  • this is the very last letter

Things to Include in an Open When Letter

Stretching the limits of your creativity is part of the fun in putting this kind of project. Specificity is key, so the best things to include are personal items, like inside jokes, pictures of you, mix tapes/CDs. Gift cards for small amounts to their favorite restaurants, coffee shops and online music apps work well.  

Inexpensive crafts are also fun. For example, if the theme is “open when you’re stressed”, you could include a piece of bubble wrap.

It’s also nice to encourage more correspondence. Write something heartfelt that answers a few specific questions about yourself and then include a blank page and an already addressed and stamped envelope. Tiny trinkets, key chains and totems that they can carry with them to remind them of you are also great ideas.
Some other ideas include:

  • if they need a countdown: a calendar with stickers to mark the days
  • if they need a reminder: something with your perfume or cologne
  • if they need a kiss: include something soft with your lip prints on it
  • if they need some warmth: send this  easy to make a DIY hand warmer with one of your gloves and a little rice
  • if they need to say hooray: include a bag of confetti
  • when they want to get funky: include a mix CD with some favorite songs
  • when they want to laugh: quotes from your favorite comedian or TV show
  • when they’re getting sick: Vitamin C or what you need to make a Hot Toddy along with instructions—honey, whiskey and tea bags.

Inspirational Quotes for Open When Letters

Handwritten quotes or well-worn advice can be just the right thing for a difficult occasion. Begin with quotes from authors or personalities you both love, or pick a few of your favorites. Here are some ideas:

When you want something romantic
“I love you without knowing how, or when, or from where. I love you simply, without problems or pride: I love you in this way because I do not know any other way of loving but this, in which there is no I or you, so intimate that your hand upon my chest is my hand, so intimate that when I fall asleep your eyes close.” – Pablo Neruda

When it’s your birthday

“Age is a question of mind over matter. If you don’t mind, it doesn’t matter” – Satchel Paige

When you need a laugh

“I went to a restaurant that serves ‘breakfast at any time’. So I ordered French Toast during the Renaissance.” – Steven Wright

When they need to feel brave

“Courage is not the absence of fear: it is acting in spite of it.”  – Mark Twain

When they need encouragement

“Do the best you can until you know better. Then when you know better, do better.” – Maya Angelou

When they need a prayer

“Here are the two best prayers i know: Help me, help me, help me, and thank you, thank you, thank you.” – Ann Lamott

When they need something, but not sure what it is

“What day is it?”

“It’s today,” squeaked Piglet.

“My favorite day,” said Pooh. – A.A. Milne

Letters can also include lovely romantic quotes for your sweetheart or a variety of inspirational quotes.

These are just a few ideas for your Open When letter project. Remember, the more specific these can be to the person you give them to, the more effective they will be. And because the letters are often written all at one time, it’s lovely to be able to think about a good place and special time to write them. Here are a few ideas for when to create your series of letters

  • During your honeymoon or the week before your wedding
  • The day before a child is born or maybe his/her first day of school
  • The week before a big move or deployment

Most importantly, don’t let this giant list intimidate you. You can write a few at a time and send them in a few installments. Or, set a limitation of 10 to 12 letters so you don’t get overwhelmed. The sizes of the letters are also up to you. You could send a book or sweater, or just keep it to small notes. Getting all these ready is supposed to be fun, so only take on as much as you feel you can handle.

An Extra-Sweet Note

If you want to make the letters extra special, send your loved one a surprise treat, like dipped strawberries. It will make the experience of opening a letter that much sweeter.