There are so many benefits to having a pen pal, but our favorite has to be the opportunity to create a long-lasting relationship with someone new. However, it can be difficult to come up with topics to write about. Although surface-level topics and small talk play important roles in the way we form relationships, talking about our memories, events we experience and our hopes and dreams for the future can help to strengthen relationships.

If you are looking to get inspired by what to write to your new far-flung friend, check out our top ten conversation starters for breaking the ice with your PenPal.

10 Ideas for starting conversations with pen pals

Two men sit writing a pen pal a conversation starter on a laptop

#1 Share your life’s journey – ask about theirs!

Getting to know someone is often about discovering each other’s past and the events that have happened to lead them to their current point. However, it is important to remember that some people may not feel comfortable talking about certain topics and may not be quite ready to share previous experiences. If you’re just starting your relationship, keep it light.

  • What was the happiest day of your life and why?
  • What was one of the scariest moments/days of your life?
  • What are your favorite memories from childhood?

#2 Hometown heroes

You could also ask about where your PenPal lives and tell them a little bit about your hometown and what makes it unique. You could even create a video of your favorite local landmarks to send along for an extra special touch and a chance to get creative. If you’re sending postcards in the traditional way (through the post), then you can simply add a link to a Dropbox folder.

Discover a new place via snail mail with conversation starters such as:

  • What is your favorite thing to do in your hometown?
  • What do people do for fun near you?
  • What is your town’s motto and do you think it fits?

#3 Family & friends

Some people love to talk about those they love, and share the special moments they have with family and friends. Learn about the important relationships in your pen pal’s life with questions like:

  • Do you have any siblings?
  • Does your family have any inside jokes?
  • What do you get up to with your friends?

#4 Downtime conversation starters

A woman sits on a bench typing and smiles

To get to know your pal’s passions and their preferred ways to relax, you could ask questions about what they do in their free time, such as:

  • What do you like to do on the weekend?
  • Tell me about your go-to self-care activities?
  • What do your vacations usually look like?

#5 Books, movies & TV

Whether it is a can’t-put-it-down page turner, the latest Box Office hit or a series that takes the world by storm, books, movies and television are everything! Best conversation starters for your pen pal related to these could be:

  • What are you watching at the moment?
  • Imagine you have to pick a character from any movie or TV show that is most similar to you. Who would you choose and why?
  • What is the best book you have ever read, and what is the worst?

Pro-tip: have a look at our 11 pen pal movie recommendations and watch them together with your pen pal.

#6 Celebrations, traditions and festivals

One of the best parts of having a penfriend is to share and celebrate social and cultural differences. Share your experiences from celebrations in your own country and ask them about theirs.

  • Does your family have any traditions they do at this time of year?
  • How do you celebrate that holiday?
  • What is your favorite celebration and why?

#7 Work and school

Although it’s not everything, work and school certainly take up quite a significant proportion of time for a lot of people. If you are passionate about learning or career-minded, share it! Plus, you never know how your pen pal’s new perspective might just help you figure out that problem that has been bugging you for a while! Give these conversation starters a go!

  • How does a typical work day look for you?
  • What are your favorite subjects in school?
  • What motivates you in your career?

#8 Let’s talk about food

Food is a great way to bring people together and to encourage conversation. Let your pal know about your favorite foods or the most popular foods in your local area or country. Ask them questions like:

  • If you were organising a dinner party, who would you invite ?
  • What would be your last meal if you could choose?
  • What is the most popular food for breakfast in your country?

#9 Goals and aspirations

Our goals in life are what give us purpose, and a great way to connect is to share your aspirations for the future.

  • When you were young, what did you want to be when you were a grown up?
  • What is something you are super excited for in the future?
  • What do you think your world will look like in twenty years?

#10 Get creative with your conversation starters!

Whilst asking people questions about themselves is a fundamental step on forming friendships, those who have been pen pals for a while may already have shared the information above. Encourage natural conversations with some ‘would you rather?’ questions. For example, ask them about their zombie apocalypse plans or even what animal they think best represents them.

Don’t forget to share your ideas too!

Need to find a new pen pal?

A pile of letters unopened on a table with flowers next to the them.

Looking for a new pen pal to practice our conversation starters on? At PenPal, we will match you up with an international pal to get to know. We will send (real!) postcards on your behalf to someone from far away, and you can then add people as friends to directly exchange postcards with them. That way, your postal address remains private!

You would certainly be in good company… Check out this article for some of our favorite celeb pen pal pairings!

Want to know more about joining PenPal? Here’s everything there is to know.


British girl turned German-wannabe- that's me! 👋 If living in Berlin has taught me anything, it's that learning about other cultures is always fun... And short of actually traveling to a country and meeting locals in person, being a pen pal has proved a great way to virtually discover people and places!

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