How To Write Your First Pen Pal Letter, Thoughtfully

So you’ve decided to be a pen pal. How cool! Being a pen pal is a lovely way to see the world through someone else’s eyes and form a connection through pen and paper. 

You don’t have to be a literary hero or English scholar to be a pen pal. All you need is to have an open mind, be curious, and long to connect. Oh, and stamps. You need stamps! 

But once you’ve got the essentials, it’s about giving someone a peek into your life and asking questions to learn more about someone else’s. Maybe you signed up to write letters to seniors, prisoners, veterans, self-proclaimed geeks, people on the other side of the world, or you’ve found one on your own through a Facebook Group or Slack channel. Or perhaps you're simply helping your kid with their pen pal letters! 

There are many ways to be a pen pal, and you can also do a few things to make the beginning of that relationship feel good for both of you. 

6 Tips For A Feel-Good Pen Pal Relationship

  • Identify who sends the first letter. Exchange letters one at a time vs. both writing one and then pick who goes first. An easy default here is picking the name that appears higher in the alphabet, but it can also be that one individual happens to have more free time at the moment. Or you’re using a program that pairs you and makes it clear!

  • Agree on a “send by” date. No one wants to be ghosted…especially by mail 🫣. Set a realistic “send by” date so that the person set to write the first letter knows when to get it to the mailman. This helps hold the first letter writer accountable and sets the expectations for the first receiver.

  • Unite on a reasonable response time. From there, agree on when to respond once a letter has been received. (I suggest 7 days, just in the beginning, to inspire momentum.) This is for accountability and expectations, which benefits both the writer and the receiver! 

  • Write your first letter! (...and queue anxiety on what to write, right? Let’s try to alleviate that.) Whether you go first or second, include a few “soft” facts to introduce yourself like your familial situation (yes, pets count!), profession, and hobbies. But because there’s more to life than small talk, describe something that made you smile recently and why. (Use details!) And always try to end with a question for the receiver.

  • Be a good listener, even on paper. It can feel natural to start a mental list of all the things you want to tell your pen pal but to make the relationship meaningful, you must leave room to take in — and respond to — what your pen pal tells you, too. Of course, some things are meant to be mentioned rather than conversation starters. Pick 1-2 things in their letter to comment on and then ask a curious question. 

  • Don’t take it too seriously! You don’t need to go out and buy new stationery for your pen-pal relationship to feel good. Of course, you want to ensure your writing is legible, but you certainly don’t need to spray your paper with Chanel No. 5. (Although, come to think of it, that’d be a cool touch.) Write with what you have, and try to have fun by personalizing it in a way that feels like you. (Think: photos, stamps, etc.) 

  • Go with the flow. Good things don’t last forever, and that goes for pen-pal relationships, too. Your response times will likely grow over time, and that’s okay! Actually, it’ll make receiving a random letter or update when you’re not expecting it feel even more special down the road. So, yes, it’s OK to go with the flow. (My one addendum here would be if you move, consider sending your pen pal your new address!) 

wellness check

It can be lonely in this big ol’ world. In fact, loneliness is rising worldwide. But we can chip away at loneliness, one letter (and therapy session) at a time. Writing handwritten letters can reduce feelings of loneliness and isolation while boosting connection, strengthening bonds, expanding worldviews, and creating a safe (and screen-free!) space for expression. 

Moving Forward

Honestly, it’s really cool that you’ve decided to do this. I hope that letter writing is one of those trends that Gen Z (and whoever comes after them) brings back, just like bell bottoms and hair clips. There’s so much we can gain from exchanging letters; doing it with someone outside your circle can be an adventure — without ever leaving your home. And that brings me to one of my favorite quotes about writing letters. (If you’ve joined one of my workshops before, you know the one.) 

“To send a letter is a good way to go somewhere without moving anything but your heart.” - Phyllis Therouxa


And there you have it! Happy writing, pal. 


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