Posted by: Adam Roper | May 27, 2009

How to write letters

In recent years writing letters has become a lost art form, placed on the back-burner in favor of more convenient and efficient forms of communication (texting anyone?). But I believe the more we give in to excess instant communication our ability to offer our simple everyday stories and experiences is lessened.

Sitting down to write a letter after writing countless messages online can feel awkward and uncomfortable, though it is a relationship with it’s own joys and insights. The pen pal relationship has it’s specific and interesting dynamics, in the same way that a close-friend relationship differs greatly from a room-mate relationship. To miss out on having a pen-pal relationship is missing out on something really beautiful.

Also, it’s just nice to receive a letter every so often from a friend. It comes with the thought that “someone stopped to think about me for a little while”. Knowing we are thought of is one of the greatest affirmations we can find- the sort that is offered instead of asked for.

So, to make a case for the art of letter writing I will offer practical advice on how to build, and maintain, any good pen-pal relationship:

1) Firstly, Find a pen pal: A pen pal could be any random person you can find to write letters to, from the girl you had a crush on in summer camp 3 years ago to the friend of a friend’s neighbor’s sister you met on facebook. You could find out the address of someone from your home town you haven’t talked to in awhile; you could start sponsoring a child through Compassion and write to him/her; or you could trade addresses with a friend who is traveling in a foreign country for a year (like Paraguay or Winnipeg).

Though in the end the best pen-pal relationships are those you stumble into randomly without trying.

2) Write a letter– If you haven’t written a letter in a long time this could be the hardest part. “What should I talk about???”; “What is interesting about my life???” are the initial reactions you may have. Start by just saying how you are doing, what things are going on in your life, what your plan for the next day/week/month is. Ask a few questions (avoid too many). If you’re still drawing a blank try describing where you are sitting, what the weather is like, what kind of tea you are drinking, what you’re listening to, etc.

If you find your first few letters feel you are grudgingly making your way through the writing process try journaling. Through journaling we find ways to articulate, in understandable terms, how our interactions with the world become the careful process of understanding. Once you have a good sense of  reflecting your thoughts and stories into a written form letter writing becomes a little easier, and way more enjoyable.

3) Creativity: A little while ago I started using construction paper to write because a) It’s cheap, b) It comes in lots of fun colors and c) It’s pretty easy to write on. As well it makes letters more interesting to open up and read. In letter writing you can try any number of things to make the finished product more intriguing for the recipient. Some suggestions:

  1. Use a square sized paper and write on the outside edges in a circle, writing in smaller squares until you reach the middle of the paper.
  2. Write a letter and fold it into an origami shape. Or if you suck at origami make a paper airplane.
  3. Soak some paper in tea, and dry it before using it to write.
  4. Go to a paper store and buy some hand-made paper… or learn how to make your own hand-made paper using recycled materials.
  5. Make your own envelope out of card-stock. Any craft store will have a wide assortment of card-stock with many artsy designs (As long as you don’t become one of those people who hang out in craft stores and own cats).
  6. Try writing a letter, or a poem, on a paper cup or a sleeve from a coffee place. You could even write a story about things you observed while enjoying the content of the cup. For extra measure you can seek out coffee places that use plain white cups instead of cups printed with inane logos and designs.

4) Tea– Keeping in mind that the letter writing process should have a fair amount of consideration for the recipient (writing a letter you know they would like) try including a few bags of your favorite tea with the letter. This will give the reader something to enjoy while they take time to ruminate on the contents of your letter.

5) Leaves– If you are writing a letter in the fall try collecting, and pressing, some red/orange/yellow leaves to send with the letter. If it’s spring time press and send a flower. Sending a bit of plant life with a letter gives the reader a sense of the season in which the letter was written, and the stuff that was growing around your house in the writing process. As well this adds to the aesthetic value of a letter.

For this reason I find the best time to write letters is in the beginning of summer and the middle of fall. Seeing the beauty of a season’s unfolding weather-changes always inspires thoughts worth sharing. Write on a rainy day, or write in place where you can see a lot of trees.

6) Photographs– If you have a spare photograph or two lying around that you have always wanted to share with a friend try sending it. Or shop around for an old camera in a thrift shop and experiment with taking actual pictures to go with your actual letter. It’s a bit more original than doing everything digitally.

7) Boxes– If you want to get really creative try spending the extra time creating a package to go with your letter. Usually this is reserved for moms who send cookies to their college kids, but whatever. Try finding a shoe-box and filling it with CDs, pictures, scraps from magazines, small paintings, poems, books found at a thrift store, etc. As well try and make the contents of the box special: Send fair trade chocolate instead of “chocolate bars”; avoid stuffing the box with too much weird stuff; Send fresh tea instead of that 4 year old box of Orange Pekoe in the back of your cupboard; Send stuff appropriate to the person you are writing to.

8 ) Honesty– Be honest with yourself in the letter. A pen-pal relationship, like all your other relationships, an actual relationship. In the same we that we try being present with a person we are having a conversation with we must try and be present in our letters. As I said in an earlier post, the conversation should never feel one-sided.

9) Finally, Etiquette– Do not be a letter stalker, sending a new one 4-6 times a week! Especially if the response you get is less than exciting. Sending way too many unwelcome letters is on par, in terms of creepiness, with stopping into a person’s house all the time even when uninvited. As with any relationship you have to have a realistic definition of what the relationship actually is- as opposed to what you would like it to be, or what you wish it could be.

The pen-pal friendship is a mutual exchange. If the other person who could care less don’t sweat over long over-worked messages.

Once you have developed a friendship with a person you write letters to try and stay in contact when possible. I usually wait until I receive a letter back before I write a new one (to ensure we are both on the same page). You have to maintain a relationship because losing a friendship is like losing a favorite shirt.

Cool. I hope you find much joy and affirmation in the art of writing letters soon.




  1. i had/have a pen pal, he is from idaho. I also have had a couple other people over the years, and I have recieved tea bags in letter’s sent my way! I also suggest in the creativity area that letter doodles are way fun to receive and give…it’s also fun to read a something about that person through a comic they drew depicting what has happened to them.

    How funny that you mention the organization Compassion…I just became a sponsor 2 days ago there!

  2. Another fun thing that I have done when on trips and bored on the plane is writing letters on the ‘airsickness bags’ that are in the seat pocket. When you start digging for it your seat mates start looking at you funny but they figure it out after you get out your pen and start writing.

  3. I think you’d make a neat pen pal! I find you fascinating!

  4. You don’t check this very often, do you? When you do, feel free to drop me a line? 🙂

    • We could perhaps discuss pen-paling. Drop me a line at, and discuss the possibility we shall.

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