50 More Things To Tell Your Penpal | Uncustomary Art

You asked for it, and here it is! After an overwhelmingly popular post, 50 Things To Tell Your Penpal, I’ve doubled your prompts to give you 50 more! That’s 100 total! I’m really glad that it’s been so well received, and I hope that it’s sparked inspiration for many introductory letters. This list is a bit more in depth and specific, for when you’re starting to get to know your correspondents better.

Personal Experiences

  • The best job you ever had
  • A funny and embarrassing story
  • Something silly you thought was true as a child
  • Describe your best friend or significant other
  • Describe your post office (or postal system if your penpal is in another country)
  • The highlights of a road trip you took
  • What you’d do/did at your wedding
  • A time you met someone famous
  • Something you wish you had done in the past but you didn’t
  • If you spent the day at the beach, what activities you would partake in
  • What kind of dreams you have
  • The last time you did something for the first time
  • The kindest thing a stranger ever did for you
  • Thoughts/experiences with couch surfing


  • Places you would like to travel to
  • Your guilty pleasures
  • How you procrastinate
  • Your tattoos, piercings, birthmarks, scars, etc.
  • Your nervous habits
  • Areas of life you’re confident enough to give advice in
  • Your pet peeves
  • What you’d want to do if you were in New York City for a day
  • Fads that should never have been brought back


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  • Your ideal party
  • Where you get your stationery and pens
  • Favorite fictional character
  • Favorite flavors and scents
  • Something that cheers you up without fail
  • How you sleep at night (clothes, doors, temperatures, etc.)
  • How you store received mail
  • Your views on the nature vs. nurture debate
  • Favorite place in your city to take someone new to
  • Favorite thing to shop for
  • Do you believe in fate, destiny, or luck?
  • Whether you know how to drive a stick shift
  • First e-mail address/screen name
  • Whether you like to be surprised
  • What kind of phone you have
  • What you thought you’d be when you grow up
  • Your heritage
  • What you’re attracted to in a new friend (or romantic partner)
  • Whether you sing in the shower
  • What super power you’d choose
  • Whether or not you mind receiving confetti in your mail
  • What one food you wish was super healthy
  • Whether you’re “outdoorsy”
  • The best piece of mail you’ve ever received
  • Least favorite chore
  • What you would name your next child, dog, hamster, car, etc.
  • Share your favorite quotes

Want a free PDF download of 50 Penpal Prompts For Children?

 | Uncustomary

Bonus: 50 Penpal Prompts For Children

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Photo credit: Lisa Rowan