50 Questions to Ask a Pen Pal

Beyond “What do you do in your free time?”

Sponsored By The U.S. Postal Service
Illustrated mailbox with letters coming out of it

I have such fond childhood memories of corresponding with my pen pal, but I remember that it was sometimes hard to keep the correspondence going. With class pen pals, your students will likely get stuck at some point. Sign up for The USPS Pen Pal Project, and have your students try this list of questions to ask a pen pal to jump start their conversations:

Getting to know you

  • Who is in your family?
  • What three words best describe you?
  • What’s a fun fact about you that most people don’t know?
  • Who is your role model?
  • What’s one thing you’re really good at?
  • What is it like where you live?
  • What’s something you like that most people dislike?
  • What’s something you dislike that most people like?


What is your favorite …

  • color?
  • movie?
  • book?
  • show to watch?
  • animal?
  • sport or activity?
  • game?
  • toy?
  • school subject?
  • band or singer?

Hopes and dreams

  • What do you want to be when you grow up?
  • If you could live anywhere, where would it be?
  • What’s one thing you would change about the world?
Image for Tips for Making the Most of The USPS Pen Pal Project

All the feels

What makes you feel …

  • proud?
  • calm?
  • frustrated?
  • scared?
  • excited?

Never have I ever

Have you ever …

  • broken a bone?
  • been in a talent show?
  • had a pet?
  • learned another language?
  • pulled out a loose tooth?

The last time

What was the last …

  • book you read?
  • movie you watched?
  • dream you remember?
  • food you ate?
  • thing that made you laugh?

What if …?

  • If you were granted three wishes, what would you wish for?
  • If you could have any superpower, what would it be?
  • If you were invisible for one day, what would you do?
  • If you won the lottery, how would you spend the money?

This or that?

  • Indoors or outdoors?
  • Cake or ice cream?
  • Pizza or tacos?
  • Mountains or desert?
  • Netflix or Disney+?
  • Winter or summer?
  • Unicorns or zombies?
  • Treehouse or castle?
  • Fiction or non-fiction?
  • Flip flops or sneakers?

Don’t have a pen pal? No problem! If you’re a 2nd-6th grade teacher, head on over to The USPS Pen Pal Project and sign up to be matched with another class. You’ll also get a free letter-writing kit mailed to you!