Sending and receiving letters and cards is fun. There’s something special about holding the card instead of viewing an email or text. They make me smile. If I got a random letter from a stranger, I think I’d be happy. It reminds me of pen pals from when I was little.

I love making people happy. So, when Christine Barba from Project Light to Life (who did an interview on this site, check it out) wrote about anonymously mailing letters of encouragement to strangers, I got really excited and added “Send a letter to a stranger” to my own list.

In the past I’ve left small notes in books at a library and put sticky notes in random places in my office. For a short time, I even volunteered for a prison rehab program where volunteers exchange letters with inmates to give them a sense of normal communication (sent via an intermediary organization, but I quit after a few months because they didn’t do as good a job of screening letters as they said they would).

With this list item, I want to mail a letter or card to a person I don’t know and who isn’t expecting it as part of a program or pen pal exchange.

I play with the idea of sending letters to a bunch of random addresses, but then I get concerned about “what if the letters don’t make it?” or “what if they think it’s weird and creepy?”

I procrastinate by writing a few small letters to seniors via the Love for the Elderly Letters of Love program, which I found out about a while ago through Kindness Blog. Love for the Elderly collects letters from a bunch of people and gives them to senior citizens in nursing facilities and group homes.  I have a soft spot for the oldest generations in our lives so this program really stands out to me. Oh, and it was started by a high school student, which is really inspiring.

For these letters, I write some encouraging sentences (something like “I hope you have a great day!”, one of my favorite quotes: “Nothing is impossible, the word itself says ‘I’m possible!'” (Audrey Hepburn), and that I hope they “will be able to see the many possibilities for happiness today.” I also put some stickers and a cute drawing on one side, because the program encourages writers to decorate or personalize the letters.

But I can’t stop thinking about sending something to a random person who isn’t expecting it, even if I know there’s a chance it may not make it to them (even cards to people I know don’t always make it to their intended recipients). I figure if it doesn’t make it, it’s not my problem. I also decide to put my return address on it, in case it’s undeliverable, so then I’ll get it back and I won’t be wondering (plus I think it makes it look a little bit less like junk mail).

As a blogger, I may be more open than the average person to getting contacted by people I don’t know, but I’m aware that not everyone feels the same. To avoid being creepy about this, I make sure that I keep the letter general, light, and don’t send it to the person’s home address.

So… I choose a nice card, write something like “Hi ___, My name is Shelly and we haven’t met. I think it’s fun to get mail, so I thought I’d spread some happiness by sending cards to random people.” Then I added the quote and also an origami crane made of pretty tissue paper. I choose a person using whitepages.com (by searching the first city that pops into my head, plus the last name “Smith” because I figure it’s a common name in the US), then I use Google to find their LinkedIn profile, which is connected to a company page with an address (so I mail it to the person at their company address).

I’m really not sure which is creepier: a random letter sent to your house, or a random letter sent to your work because someone took three steps to find out where that is. I still think the house would be a bit worse… Agree or disagree?

Now that I’m in the card writing mode, I also send a few more to people I know, just to say hi and thanks, which probably makes me happier than the letters to strangers, because I know how they’ll react and that they’ll appreciate it.

Overall, this was a fun thing to do, but I’m worried that it might give people a weird or stalkerish feeling, and that’s the opposite of what I hope they’ll feel. If I do this again, I’ll stick with leaving letters in random places like cafes, the bus, the library, etc. or go through an organization. Maybe next time I’ll send some letters through programs that facilitate letters to members of the military (active, wounded, or retired; some also send to families of service members). I thought about it this time, but I couldn’t come up with what to write to them. Everything seemed so trivial. Do you have any tips about what to say to encourage or support service members and their families? Have you ever written to a stranger? Tell me about it in the comments.

Note: If you’re going to do this through an organization, please be sure to check the guidelines, not only for the mailing address, but also to make sure they can accept whatever you’re sending. Sometimes there are strict rules about what they want or don’t want you to include. Also, if you are writing through a program for military service members, most of these programs have very strict rules about what you can and can’t send, so please do your research before you send anything.

Dec 2016 Update! The person I sent the card to at her work address loved it! She sent me back one last month and it was so nice to get a thoughtful card back from a stranger. Makes me want to send some more! 🙂