You've got questions
The ones parents ask most.
What if my child's pen pal stops writing back?
It happens — kids get busy, and sometimes a match just doesn't click. If your child's pen pal goes quiet, let us know. We'll check in, and if writing has truly stopped, we'll find your child a new match. No child gets left waiting at the mailbox.
How does address sharing work?
When two children are matched, MailDay introduces their parents by private email — and addresses are exchanged directly between parents, never publicly and never in a group setting. Your child writes their pen pal's first name on the envelope; you address the outer envelope. Many families also set up a PO box just for letters — their child's very own mailbox — and we think that's a wonderful first step. (More in First Mailbox & Safety.)
What does MailDay look like for a 3-year-old?
MailDay Minis is built for exactly this age. Instead of a writing prompt, Poppy sends a drawing mission — so your child draws their reply. We love when a grown-up adds a sentence or two underneath, in your child's words: "Mira drew her cat because he sleeps in the laundry basket." It takes thirty seconds, it shows your child what writing is, and it gives their pen pal something to read out loud. Their pen pal gets a drawing and a few words in the mail — which is honestly better than most letters anyway.
How does the matching actually work?
When you sign up, you'll tell us about your child — their age, interests, and personality. MailDay matches on exactly those things: kids close in age, with interests in common, and enough difference to keep the letters genuinely interesting. Matches are made in a weekly batch every Friday.
Can I cancel any time?
Yes, truly — no annual commitment, no cancellation fees, no guilt trip. If you just need a break, you can also pause your membership for a little while and pick back up when the time is right. And if your child has a pen pal when you go, don't worry — we'll take good care of their match and help that other child find a new friend. We'd always rather you leave the door open than feel locked in.
What's in the monthly pack?
Your monthly pack is a digital download — you print it at home on standard paper, which means it lands in your inbox on the 1st with nothing to wait on in the mail.
Core pack (ages 6–12): Poppy's adventure letter, two themed stationery sheets, a fold-and-seal envelope template, a conversation prompt card with five questions, a fun fact card, a drawing prompt, and a themed cutout sheet for decorating letters and envelopes.
Minis pack (ages 3–6): Poppy's letter in a read-aloud version, a color-in sheet, an activity sheet, a fold-and-seal envelope template, a drawing prompt, a themed cutout sheet, and a parent card with sentence suggestions.
Kids cut out and fold their own envelope — that's half the fun. All you'll need is a printer, paper, scissors, a glue stick or tape, and a Forever stamp.