The Art of the Handwritten Letter: Pen Pal 101

This second article of a three part series by Lisa Shobhana Mason will give you great tips for writing and sending your first pen pal letter. You can read her first post, The Art of the Handwritten Letter, to get information on finding a pen pal.


Letter Safety

Many pen pal matching sources are free, while others may charge a small membership fee. They are usually run by letter loving individuals who want to share their passion with the world. In either case, these resources are not in a position to run background checks on potential pen pals. I’ve corresponded with dozens of people and have yet to have anyone show up on my doorstep without invitation. These days a lot of personal information, including your address, can often be found on the Internet. However, if you have safety or privacy concerns around corresponding with a stranger there are a few precautions that you can take.

  • Rent a post office box- For a small fee, you can keep your home address private and you can support our financially challenged USPS. Contact the post office nearest you for rates and details.
  • Use a nickname or alias, but before you do, check with your postal carrier to be sure that you will receive delivery of mail addressed to that name. This is more likely to be an issue if you live in an apartment rather than a house.
  • If you are under 18, you should check with a parent or legal guardian before joining a pen pal service or posting personal information on the internet.

Getting Started with Your First Letter

Your first letter to your pen pal should be more like a preview of coming attractions rather than revealing the entire story of your life. Introduce yourself with a few basic details. Always keep in mind that you should save some information for future letters. A little mystery goes a long way toward keeping up an interesting correspondence. For example, in your introductory letter you might reveal that you live with your boyfriend and in subsequent letters you might tell the story of how you met or reveal a funny story from your courtship. Revealing the whole story all at once can not only be overwhelming for the reader, but it leaves you less to write about in the future.

Ask questions! Remember that you’re not writing a monologue! You’re participating in a dialogue. Including at least two or three questions in every letter keeps the dialogue going and lets your pen pal know that you’re really interested in getting to know them and learning more about his or her life.

Identifying Your Inner Letter Writer

I find that a really great letter writer usually falls into one of the following categories:

  • The Adventurer– You are someone who travels frequently or you’re very involved with community activities. You write about your travels. You describe that local customs and cuisine, and tell your pen pal about the sites that you visited. If your adventures are closer to home, you write about local festivities and their history. Every city or town has its own unique celebrations, observances and local characters. You know that what may be commonplace to you, could be completely new and interesting to the person that you’re writing to.
  • The Researcher– You’re an avid reader and really you’re into a particular topic, author or genre of literature. You write about what you’ve read, what you’ve learned, and why you’re so fascinated by this topic. If your pen pal shares your interests then you completely geek out over your favorite things. If your passion is something that is new to your pal, your enthusiasm may inspire him or her to want to know more about the subject at hand. The Researcher also includes film buffs and music enthusiasts.
  • The Chatty Cathy– You’re a BFF who shares the details of your daily life, like what you made for dinner last night and the pros and cons of your latest date. You like to ask your pal for advice and suggestions and you ask a lot of questions about his or her daily activities. You are comfortable discussing just about anything and you are easy to get to know.
  • The Mail Artist– Writing a long a detailed letter is not necessarily  your thing. You’re more into creating a beautiful piece of mail art using items like rubber stamps, washi tape and bits of ephemera. From creating your own stationary to adorning an envelope to choosing which stamps to use, your love of the letter is more about craft than content. You are best suited to corresponding to someone who is equally crafty. You can exchange mini works of art, as well as sharing crafty tips, techniques and sources.

My next and final article will feature a profile of one of my favorite mail artists. She will share how she became interested in mail art and will show us some of her favorite works. Until then, happy corresponding!

Lisa Shobhana Mason is the author of the North Light books Yarnplay and Yarnplay at Home. She is also a pen pal matchmaker for creatives, aged 25 and older, and works her letter writing magic at

Want more about ways to create with writing? Check out:


Improve your mixed media art with books, DVDs, downloads & from the North Light Shop

Sign up for your FREE Create Mixed Media email newsletter for great tips, projects & more

Get unlimited access to mixed media art instruction ebooks

Download free mixed media desktop wallpapers

You may also like these articles:

This entry was posted in Guest Posts, Mixed Media Blogs and tagged . Bookmark the permalink.

One Response to The Art of the Handwritten Letter: Pen Pal 101

  1. maneki says:

    Another good way to get penpals is to find a friend or relative who are in the penpal community. My sis got her first PPs via a cousin of ours who had houndreds of PPs around the world at that time (before the age of social media). After that she mostly found her pals via the FBs that travel the world. When a friend of my sister’s wanted pals, my sis found her some by asking her PPs if they wanted to write to the friend and by including her address in FBs.

    You never know who will reply on an FB or whether it will eventually return to you, but it can be fun and you get to see how the pamphlets travel, criss crossing the world. So far, the only problems my sis have had during all these years have been one guy who asked for money (but gave up when she was upfront with not being rich enough to give away expensive things) and one who wanted to be her boyfriend (she ignored him and in the end he gave up). But not giving out phone numbers is a good start. Wait with that until you become pals and see the sharing as a sign of mutual friendship and trust. Have heard of someone who suddenly found her PP (from a poor country, hoping for a better life) on her doorstep, but whether true or rumour who knows?