The Perils of Pen Pal-ing: Missing Letters and More!


At its core, snail mail is a hobby that requires a lot of faith in the universe–and by “the universe” I mean “the intricate postal network that somehow allows me to send letters across continents and oceans for $1.15 or less.” Most of the time, all goes according to plan: letters arrive, gifts are exchanged, and friendships are forged between eccentric strangers who share a fondness for writing and washi tape.

But what happens when it doesn’t?

I’m coming up on my two-year anniversary of actively partaking in the snail mail/pen pal community. I’ve easily sent and received over a hundred pretty envelopes since January ’15, and I’m no stranger to the quirks and pitfalls of letter-based communication.

Read on for some thrilling tales of the most common challenges I’ve encountered in the pen pal world: though I’ll say up front that the occasional hiccup by no means outweighs the joys of receiving mail!

1. The Mary Celeste of mail

Just like a nineteenth-century brigantine appearing adrift in the middle of the Atlantic after being lost for months, sometimes letters vanish for several weeks and are rediscovered ages later. The international/domestic distinction doesn’t seem to come into play here: I’ve had a letter take two months to reach Germany and another take three months to get to Utah. Where do these “ghost letters” go on their mysterious journeys, I wonder?

2. Shouting into the void

Let me first make it clear that there’s one thing that won’t appear on this list: pen pals who take a long time (i.e. months to years) to write back. I have no problem with that, surprisingly!

I will never be unhappy to see a new letter–even if it’s a response to something I sent the person months ago. It becomes almost a Prodigal Son-type situation, strangely enough: the longer it’s been since I’ve heard from you, the happier I’ll be to hear from you again! (Yeah, I know, it’s weird.)

The one thing, however, that saddens my little heart is when I send a first letter to a prospective/new pen pal and never hear anything back ever. First letters are always a bit awkward, and putting yourself out there like that without any acknowledgement can be a little disappointing. We’ve all been there, right?

3. Return address chicanery

What’s your city of birth?  That’s probably a really easy question for you to answer…unless you’re like me and the many other people from rural hometowns who were technically born in a nearby city but lived and grew up in another town. Though I know which one’s right and which one’s not applicable, it takes me a few minutes to sift through them and pick the correct answer.

Same thing happens with return addresses, sometimes. I’ve had a few pen pals live in small towns but maintain their P.O. boxes in neighboring cities–except they wrote the small town in their return address by accident, which I dutifully copied and used as their address! Always good to double-check.

4. Between a letter and the deep blue sea

If you, like me, are a strange introvert with a desperate fear of Awkward Emails, I’m sorry to say that even snail mail can’t help you escape them! If I don’t receive a reply for a few months, I start to wonder what I should do next. Should I send the pen pal a note, or not? I don’t want to make them think that I’m pressuring them to write back quickly…but what if they never received my letter? Or what if they did sent me a letter and it got lost? How soon is too soon to check in?


Writing letters isn’t always smooth sailing: but it’s always quite the adventure! What are some of your tales of snail mail woe?


  1. I did something perhaps perceived as odd recently. I had a sudden wave of penpal requests and I was amazed by it, but soon realised that I wouldn’t be able to commit to so many people.
    One girl had given me her address, and so was expecting something. Rather than messaging her online, I posted a little quick note to her to say sorry I wouldn’t be able to write to her properly at least for the time being as I had taken too much on.
    I thought that writing to her might be a nicer way of saying sorry, especially as I had already said I’d write as soon as could.
    I think I will write to her properly when my outgoing list reduces a little, but yeah, like I said I guess it might come across as an odd thing to do!? I have no idea.

    • I think that was absolutely the right thing to do, and it was very considerate & thoughtful of you! πŸ™‚ 100% of the time, I would *so* much rather get a quick note or email letting me know that someone was busy than hear nothing…but at the same time, I understand why people might feel awkward about doing that. In any case, I’m sure the recipient of your note will be understanding and appreciative!

  2. I have been penpalling for almost 50 years and what you say sounds familiar to me, oh yes ! But I turned to emailing now cos I have quite a few penpals all over the world and the costs for stamps was getting really expensive here in Belgium. But occasionally I write a snailmail letter to a few of my pals as I know they love it. You can’t compare a real letter with an email but they both have advantages.When I learned how easy, quick and cheap it was to sent an email oversees I was soooo surprised ! On the other hand nothing beats getting a nice envelope with a handwritten letter and pictures in it ! Have you ever tried Interpals to look for penpals ? In the old days we got addresses at school or in magasines and there were even special penpal magasines with about 1000 pictures and addresses ! I loved going through them ! Have fun with your penpalling !

    • Thanks so much for your comment, and for sharing your penpalling stories! πŸ™‚ Wow, I can’t imagine getting a magazine full of potential pen pals; that sounds like so much fun! It’s funny how much I rely on the Internet to meet snail mail pen pals…we may be sending each other letters, but we need emails to meet in the first place. Though I agree that emailing is such a wonderfully fast & affordable way to keep in touch with people around the world, too. Anyway, happy mailing to you as well!

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