What will my pen pal and I receive in the mail?

You'll both get a kit in the mail that includes:

  • Pre-stamped, pre-addressed envelopes for your pen pal

  • Lined stationery where you can spill your heart out

  • Curated question prompts to spark meaningful conversation

In short: everything you need to connect, reflect, and be ready to send.

How will I know which letter to send?

In your kit, each envelope set will be labeled with a number. You and your pen pal will both start with #1 and go numerically from there. This way, you are both answering the same prompt at the same time!


Does my pen pal need to order, too?

Nope! One order covers two people. This is all about making connection easier, after all.


What kind of questions will we be asked?

We don’t want to spoil all the surprises, but here’s a little peek:

Each subscription comes with its own tailored question path—because let’s be real, you’d ask your best friend different things than you’d ask your dad. The questions build gradually over time, starting light and going deeper as the months go on. From beginning to end, all of our questions are geared towards connection and span far beyond normal small talk.

How will my pen pal know I gifted this to them?

With their delivery, your pen pal will receive a custom “Ticket to Connection” card. It includes simple instructions, a quick intro to who we are, and—most importantly—your name, so they know exactly who to thank (and write back to!).

I want to gift this for a birthday or a holiday. How can I schedule my first delivery?

We usually need about a 5 business days to process your order and work our magic (team of 1 over here!), but if you're on a tight timeline, send us a message on our contact page. We'll do our best to make it happen.

Can I have multiple pen pals at once?

Absolutely—the more, the merrier! Just keep in mind that if you have multiple pen pals within the same subscription type (like two active "Dear Friend" subscriptions), you may receive the same questions for each. That’s because each category follows a preset question sequence that gradually builds over time. So, while the connections will be unique, the prompts may repeat.