100 Fun & Interesting Questions to Get to Know Your Pen Pal

Coming up with new and fresh questions can be challenging when you’ve written a ton of pen pal letters. I’ve compiled a list of one hundred questions to try. This list is not exhaustive, but hopefully it gives you some ideas when you’re feeling stuck in a rut!

Coming up with new and fresh questions can be challenging when you’ve written a ton of pen pal letters. I’ve compiled a list of one hundred questions to ask your pen pal for your reference. This list is not exhaustive, but hopefully it gives you some ideas when you’re feeling stuck in a rut! I tried to think of some unique questions to ask your snail mail friends to keep things interesting. Take a look below and save this list for your reference if you like these questions.

15 Get-to-Know-You Questions

To kick things off, here’s a list of standard questions to get to know your new pen pal. These questions are typically asked or discussed in the first letter with your snail mail friend. 

  • When’s your birthday?
  • How big is your family?
  • What’s your astrological sign?
  • What’s your dream job?
  • How would you describe your fashion style?
  • Do you wear makeup? Everyday or rarely?
  • Describe your hair style & color.
  • Do you wear any type of glasses?
  • Favorite school subject?
  • Do you have a favorite book?
  • Do you have an all-time favorite song?
  • Did you have a favorite childhood snack?
  • What’s your favorite ice cream flavor?
  • Do you have a favorite candy bar?
  • What’s your strongest childhood memory?

10 Travel Related Questions

People say travel is good for the soul. Talk with your pen pal about their travel past and their travel dreams! Whether it’s a local destination or a completely brand new country, there’s so much to see all around you. 

  • What’s your dream travel destination?
  • How many places have you been to?
  • What’s your favorite local getaway spot?
  • Do you prefer hotels or hostels?
  • Have you ever flown first class?
  • What was your favorite travel location?
  • What funny memory do you have from your travels?
  • How would you describe your travel style?
  • What are your must-bring travel essentials?
  • Are you a light or heavy packer?

15 Food Related Questions

Food is an essential, but not everyone is a foodie! Ask your fellow foodie pen pal what their favorites are, what they hate, or what reminds them of home. 

  • Are you a picky eater?
  • What dish did you always eat as a child?
  • What’s your favorite restaurant in your area?
  • Do you like to cook new dishes or do you cook what you’re familiar with?
  • What’s your favorite dish from X cuisine (i.e. Chinese, French, Italian, Mediterranean)?
  • What is something you will absolutely not eat?
  • What “quirky” food have you tried?
  • Have you ever eaten any other animal meat apart from seafood, poultry, beef, or pork?
  • What’s your go-to breakfast?
  • Do you like brinner aka breakfast for dinner?
  • What’s your favorite pie flavor?
  • Do you like pickled foods?
  • Can you handle spicy foods? 
  • If you had to pick one cuisine to eat for the rest of your life what would you choose?
  • What is one cuisine or food you have always wanted to try?

20 Film & Entertainment Related Questions

If you’re an entertainment lover, here are some questions to use as inspiration. The film industry is vast and there are tons of thoughts you can learn from your pen pal! Whether it’s about Disney or Studio Ghibli, there’s so much to discuss with your friend. 

  • What’s your all-time favorite TV show that you can watch on repeat?
  • Do you have a favorite Disney film?
  • Are you a Star Wars or a Star Trek fan?
  • Who’s your favorite Avenger?
  • What are your thoughts on Gal Gadot as Wonder Woman?
  • Do you have an all-time favorite Studio Ghibli film?
  • What YouTuber do you not care to watch?
  • What’s your current favorite Netflix series?
  • What are your thoughts on the film Call Me By Your Name?
  • Do you have an all-time favorite movie?
  • Who is your favorite YouTuber?
  • Which YouTuber have you been watching the longest?
  • What types of TV shows do you prefer to watch? 
  • Do you like watching award shows?
  • What TV show did you always watch with your family as a child?
  • Do you have a favorite actor/actress?
  • What anime show(s) do you like watching?
  • Which actor/actress would you choose to play you in a biography?
  • If you could write a movie script, what would the plot be about?
  • Have you ever had any celebrity sightings before? 

10 Fun & Quirky Questions

Keep things light with your pen pal and ask them about their preferred super power or tell them to decide between some hard choices. 

  • Would you rather see the future or travel back to the past?
  • Would you rather have photographic memory or be able to speak any and all languages in the world?
  • What would you do with a million dollars?
  • If you could write a book about your life, what would the title of it be?
  • What super power would you want and why?
  • If you could teleport, where would you teleport right now?
  • What kind of old person do you think you’ll be?
  • Would you rather eat a fried tarantula spider once or tell people your deepest secret every time you met someone new?
  • What fictional character do you think would be boring in real life?

10 Personal & Deep Questions

These questions are definitely more suited for pen pals that you are close to. Personal questions can make a person feel vulnerable, so be mindful of what you choose to include. If you want to bridge the gap with your pen pal but you’re unsure, ask them in a letter if they’re comfortable with personal questions. 

  • What do you love about yourself?
  • Do you mind sharing an embarrassing story?
  • Do you have any regrets?
  • Are you more likely to avoid confrontation or face it?
  • When was the last time you cried and why?
  • What do you look for in a significant other?
  • What do you think is a waste of money?
  • Do you trust your first impressions on people?
  • What makes you feel better when you’re upset or angry?

 I hope this huge list will give you some inspiration with your next pen pal letter!

x Leslie

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100 unique questions to ask your new pen pal in your snail mail letter