50 Pen Pal Questions to Ask in Your Next Letter
Sometimes the hardest part of writing to a pen pal isn't starting the letter. It's knowing what to ask next.
One of the nicest things about having a pen pal is getting to know someone slowly. There is no need to fit an entire conversation into a few quick messages. You can ask something, send your letter away and discover the answer days or even weeks later.
But after the usual How are you? and What have you been up to?, it is easy to run out of ideas.
These 50 pen pal questions give you something a little more interesting to ask, whether you are writing your very first letter or have been exchanging mail for years. Some are light and easy, some are more personal and others are simply fun.
You certainly don't need to ask all 50. Pick two or three that make you genuinely curious about the person on the other side of the envelope.
Questions to ask a new pen pal
When you have only exchanged a letter or two, you probably don't know much about each other's everyday lives yet. Start with questions that give the other person room to tell you something about themselves without making the letter feel like a questionnaire.
What does an ordinary day look like for you?
What is your favourite thing about where you live?
What do you usually do on a free Sunday?
What are you reading, watching or listening to at the moment?
Do you have a hobby you could talk about for hours?
What is something small that always makes your day better?
Are you more of a morning person or a night person?
What is your favourite season and why?
What is somewhere near you that you think everyone should visit?
What is something you are looking forward to right now?
These questions give you plenty to come back to in your next letter too. If your pen pal tells you about a favourite book, a weekend ritual or somewhere they love going, remember it. Following up on something from an earlier letter often creates a much better conversation than continually introducing new topics.
If you're staring at the rest of your own blank page too, What to Write in a Letter: 30 Personal Letter Writing Ideas has plenty of ideas for the parts between the questions.
Fun pen pal questions
Not every letter needs to lead to a meaningful revelation. Sometimes the questions that seem slightly unnecessary produce the answers you remember.
What food could you happily eat every week?
What song do you know almost every word to?
If you could spend tomorrow anywhere, where would you go?
What is your most rewatched film or television show?
What is something you love that everyone else seems to dislike?
What is the best thing you've bought recently?
What is your ideal way to spend a rainy afternoon?
Which three things would you take to a desert island if practical answers were banned?
What is one trend you will never understand?
What is a completely ordinary thing you're strangely particular about?
You can answer the question yourself before asking it. Instead of simply writing What's your ideal rainy afternoon?, tell them yours first. Suddenly a question becomes part of the letter rather than a list attached to the end.
Pen pal questions about favourites
Favourite-things questions are classics for a reason. They are easy to answer, but they can also tell you surprisingly much about someone.
What is your favourite book you've read in the last few years?
What is your favourite meal to cook for yourself?
What is your favourite place you've ever visited?
What smell instantly makes you think of something or someone?
What is your favourite thing about your home?
What is a song you never skip?
What is your favourite little tradition?
What is your favourite way to spend time offline?
What is one possession you would hate to lose?
What is your favourite memory from the past year?
Questions to get to know your pen pal better
Once you have been writing for a while, there is naturally room for questions that go beyond favourites and weekend plans.
You don't have to make every exchange deep. But letters can make it easier to talk about things that rarely come up in everyday conversation because both people have time to think before answering.
What is something you've changed your mind about in the last few years?
What makes you feel most like yourself?
What is something you wish you had more time for?
What is something you've become better at saying no to?
What kind of people make you feel most comfortable?
What is something you're proud of that you don't talk about very often?
What did you imagine your life would look like when you were younger?
What is something you would like to learn one day?
What makes somewhere feel like home to you?
What is something you hope stays exactly as it is?
There is no need to ask personal questions simply because you've exchanged a certain number of letters. Let the friendship decide how personal the correspondence becomes.
Questions about memories and stories
Questions that ask for a story rather than a one-word answer are particularly good for letters. They give your pen pal somewhere to take the conversation.
What is one of your earliest memories?
What birthday do you remember particularly well?
What is the best trip you've ever taken?
What is something you loved doing as a child?
Who had a big influence on you when you were growing up?
What is a family tradition you remember from childhood?
What is something that went completely wrong but makes you laugh now?
What place from your past would you like to visit again?
What is a small moment from your life that you still remember for no obvious reason?
What is a story about you that I probably wouldn't think to ask about?
That last question might be my favourite. We usually ask people about the things we already know enough about to ask. Giving someone an open space to tell you the story they want to tell can take a letter somewhere completely unexpected.
How many questions should you ask your pen pal?
There is no rule, but two or three questions in one letter is usually plenty.
A pen pal letter should still feel like a conversation, not an interview. Share your own stories, respond to things from their previous letter and let questions appear naturally along the way.
You might spend half a page responding to one answer from their last letter and ask only one new question. That's still a good letter.
If you're completely new to exchanging physical mail, this guide to snail mail, letters and mail clubs is a good place to start.
A simple way to make your questions feel less like an interview
Try this:
Answer first. Ask second.
Instead of:
What's your favourite season?
You could write:
I think autumn will always be my favourite. I love that first week when you suddenly need a jacket again and evenings start feeling cosy instead of endless. What's yours?
The question is exactly the same, but now your pen pal has something to respond to beyond the question itself.
You can also pick up details from previous letters:
You mentioned that you had started pottery classes. Are you still going? Have you made anything you actually like yet?
Those questions often feel much more personal than anything you could find on a generic list because they show that you were paying attention.
You don't need the perfect question
The best pen pal questions aren't necessarily the cleverest ones.
They're the ones you actually want to know the answer to.
So choose a question from this list that makes you think, I wonder what they would say to that. Write your own answer first if you want to. Then send the letter and let the conversation continue when the next envelope arrives.
Sometimes that's the lovely thing about correspondence.
You don't get every answer immediately.
