130 Conversation Starters and Questions To Ask Your Pen Pal

130 Conversation Starters and Questions To Ask Your Pen Pal

Hello dear readers,

It is rightly said that a conversation is much more than words, it’s the eyes, smiles, and the silence between the words.

A good conversation fills the mind with great pleasure, it’s like food for the soul.

Who knows the importance of a good conversation better than a pen pal after all? The beauty of getting to know a person through written words and then turning that bond into a bond of tight friendship is nothing less than magic.

asian woman reading letter by lake
I remember my days as a newbie to snail-mailing and how I used to struggle with keeping the conversation going. Eventually, I came across multiple snail mailers and pen pals who left me amazed at their skills to keep the letters coming. They always had something or the other to share and something or the other that they wanted to know about me. That’s when I realized the importance of conversation starters.


Be it your first letter to your new pen pal or someone you have been writing to for years, it’s always good to come up with new topics to kick start a conversation. To keep a conversation alive is also an art. So let me help you polish these skills of yours and become an indispensable artist.


This long list is going to be full of various kinds of questions that you can ask your pen pal. Questions related to their likes, dislikes, their favorites, their last times, and so on. You can pick up a question depending upon the level of bond you have with your pen pal or what kind of bond you want to establish with them.


If you are looking forward to receiving the letters from your pen pal for years then this article is going to be one of those bookmark-worthy articles. So let’s get started.


General questions

I consider these questions to be the ones that are thrown at our pen pals generally during the first few exchanges.


  1. How is the city where you live in?
  2. Do you live along with your family?
  3. Are you a student or working?
  4. Do you enjoy being in the field you are in?
  5. Which season is your favorite?
  6. What are you most afraid of?
  7. What do you do in your free time?
  8. What are your favorite hobbies?
  9. How would your friends describe you?


  1. Do you have any favorite childhood memories?
  2. Which is your all-time favorite movie to watch?
  3. Who are your favorite actors and actresses?
  4. What is your favorite food?
  5. What are your favorite memories that you can’t get over?
  6. Which TV series can you watch on repeat?
Woman reading letter

Likes and Dislike

  1. Do you like watching Kdramas or listening to Kpop?
  2. Do you like going out for long walks?
  3. Do you like road trips?
  4. Do you like listening to Ebooks?
  5. Do you like having nicknames? Do you have any?
  6. Do you like pineapple on pizzas?
  7. Do you like spending time with your family?
  8. Do you like being surprised by someone?

Do you?

  1. Do you know how to play any musical instrument?
  2. Do you know how to swim?
  3. Do you play any sport?
  4. Do you have any role models?
  5. Do you believe in the existence of God?
  6. Do you believe in Ghosts?
  7. Do you use social media and what are your opinions about it?
  8. Do you have any talent that the world is yet to know about?
  9. Do you sing in the shower?
  10. Do you have any siblings?
  11. Do you believe in astrology?
  12. Do you have any pets?
  13. Do you believe in Unicorns or Zombies?

Dreams, hopes, and ambitions

  1. Where do you see yourself 10 years from now?
  2. What dreams of yours have been fulfilled?
  3. What do you want to achieve in the next 5 years?
  4. What are some of your biggest dreams?
  5. Do you consider yourself a hopeful person?
  6. Are you ambitious enough to fight against the world to fulfill your dreams?
  7. What value do your dreams and ambitions hold for you?
  8. What do you wish to change in this world?
holding and reading letter

Feelings and emotions

  1. How does thinking about your past make you feel?
  2. How does thinking about your future make you feel?
  3. How do you feel about getting married?
  4. What makes you extremely emotional?
  5. How does the thought of death make you feel?
  6. What makes you feel proud of yourself?
  7. What makes you calm?
  8. What makes you lose your temper?

Have you ever…

  1. Maintained a daily diary?
  2. Cheated on someone?
  3. Broken a law that you should not have?
  4. Stolen something?
  5. Tried any adventure sports?
  6. Met any celebrities?
  7. Been a bridesmaid or a bridegroom?
  8. Won a lottery or any big gift?
  9. Broken a bone or got stitches?
  10. Been so drunk that you don’t remember anything about it?
  11. Seen any studio ghibli movies?
  12. Been a part of any talent show or a reality show?
  13. Tried learning a foreign language?
  14. Hurt someone close to you?
  15. Have you ever traveled abroad? 
  16. Moved out of your house or changed cities?
Letter being read

What if?

  1. What if you had any superpower? What would you do with it?
  2. What if you win a lottery for $1 million? What would you do with that money?
  3. What if you were stranded on an island and had the option of having only one thing with you? What would it be?
  4. What if there was a genie who could grant you 3 wishes, what would you wish for?
  5. If you could eat only one type of food for the rest of your life what would it be?
  6. If you could use only one social media platform then which one would it be?
  7. If you could change the education system then what’s the one thing that you would change?
  8. Where would you choose to live if you had the option of living anywhere in the world?
  9. What if you had the power of being invisible for one day? What would you do?

The last time

  1. Which is the last movie that you watched?
  2. Which is the last book that you read?
  3. Who is the last person you spoke with?
  4. Which is the last place you traveled to?
  5. Which is the last most delicious food item that you ate?
  6. The last interesting dream that you remember?
  7. When was the last time that you felt like life is amazing?
  8. When was the last time that you felt like giving up?
  9. Describe the last day of your school or college?

This or that

  1. What do you prefer more? Staying indoors or outdoors?
  2. Are you a cat person or a dog person?
  3. Do you like reading books or watching movies?
  4. Do you like watching cricket or football?
  5. Are you an emotional person or a practical person?
  6. Do you like to give gifts or receive gifts?
  7. Do you categorize yourself as an extrovert or an introvert?
  8. Do you like eating spicy food more or sweet food?
  9. Do you prefer Ebooks or hard copies?
  10. Do you prefer to write down on paper with a pen or note down things digitally?
  11. Are you a tea person or a coffee person?
  12. What do you prefer more? Beaches or mountains?
  13. Do you prefer staying in hotels or hostels?
  14. Which is better according to you? Winters or summers?
  15. Do you prefer fiction or nonfiction?
  16. Are you a sneakerhead or a flip-flop kind of a person?

Down the memory lane

  1. How were your school or college days?
  2. How was your childhood?
  3. What is the best message you have received so far?
  4. Who was the last person you went out with?
  5. When was the last time you laughed hard?
  6. When was the last time you cried?
  7. Who was your first pen pal?
  8. How did you get into snail-mailing?
Woman reading letter

Personal questions

  1. Are you in a relationship?
  2. Can you describe the place where you stay?
  3. What was your first dating experience like?
  4. How old were you when you started dating?
  5. Do you have any birthmarks?
  6. Have you ever broken someone’s heart or someone broke your heart?
  7. What kind of bond do you share with your siblings?
  8. What kind of bond do you share with your parents?
  9. Have you ever been in a toxic relationship?
  10. Have you ever seen disharmony in your family?


Based on this gigantic list I am pretty sure that you will get an idea of what you can ask of your pen pal. These questions will bring you much closer and help in building a beautiful bond of friendship.

One thing is for sure the letters will keep coming since you’ll never run out of questions or topics to talk on. You can even experiment with the way that you want to ask questions to your pen pal and maybe try to even frame something like a quiz out of this.

You can come up with many more questions apart from the ones mentioned above. If you have any more creative questions that you think would be great as a conversation starter then don't forget to share them with me and our entire snail mail community.


Happy Mailing!!!


Back to blog

Leave a comment