FAQ
About the Exchange
How does the anonymous exchange work?
Each month, you’ll receive a prompt via email. You submit your letter through a simple form by the 10th. I pair your letter with another subscriber’s, and around the 15th-18th, you’ll receive their letter via email. They receive yours. You never know who they are, and they never know who you are.
Will I know who my pen pal is?
No. All exchanges are completely anonymous. No names, no email addresses, no identifying details are ever shared. That’s what makes this space safe for honesty.
Can I respond to the letter I receive?
No. Each exchange is a one-time connection. You write once, receive once, and that’s the complete exchange. Next month brings a new prompt, a new pairing, and a new stranger. This isn’t about ongoing correspondence—it’s about single moments of connection.
What if I don’t like the letter I receive?
Every letter is an act of vulnerability from another human being. You’re invited to read it with compassion, even if it doesn’t resonate with you. If a letter violates our guidelines or makes you uncomfortable, please let me know immediately.
Can I skip a month?
Absolutely. You can participate every month, or only when a prompt speaks to you. Your subscription continues, and you’ll still receive the published archive each month. Just write when you feel called to.
What if I miss the submission deadline?
You’ll need to wait until next month’s prompt. Deadlines ensure I have time to thoughtfully pair letters and send exchanges on schedule.
About Paid vs Free Subscriptions
What do I get as a paid subscriber ($8/month)?
Monthly prompts delivered to your inbox
Ability to submit your anonymous letter
Receive one anonymous letter from another subscriber each month
Optional: Have your letter published in the monthly archive
Support the continuation of this project
What do I get as a free subscriber?
Monthly published archive of selected anonymous letters
Access to the growing collection of past letters
The ability to read and witness the community’s truths
Can I upgrade from free to paid anytime?
Yes! Upgrade at any time. You’ll be included in the next month’s exchange cycle.
Can I cancel my paid subscription?
Yes, you can cancel anytime. You’ll continue to have access until the end of your billing period, and you can always rejoin later.
About Privacy & Safety
How do you protect my anonymity?
Your email is used only for matching and sending letters. It’s never published, never shared with other subscribers, and never visible anywhere. I’m the only person who sees it, and I guard that information carefully. When your letter is exchanged, all identifying information is removed.
What happens to my letter after the exchange?
If you opt to keep it private, only you and your anonymous pen pal will ever see it. If you consent to publication, it may be included in the monthly archive sent to all subscribers. You always have the choice.
Can letters be traced back to me?
No. Letters are submitted through an anonymous form. If you don’t include identifying details in your writing (like your specific job, location, or names), there’s no way to trace it back to you.
What if someone writes something harmful or inappropriate?
I review all submissions before matching. Letters that violate guidelines (hate speech, harassment, explicit content, promotion) are not exchanged. If you receive something that concerns you, please contact me immediately.
About Writing & Prompts
How long should my letter be?
There’s no word limit. Write as much or as little as feels true. Some letters are a single paragraph. Others are pages. Both are valid.
What if I don’t know what to write?
The prompt is there to guide you, but you don’t have to follow it exactly. Write what you need to write. Write what you’ve been holding. Trust that it will reach someone who needs to read it.
Can I submit more than one letter per month?
No. Each subscriber submits one letter per prompt. This keeps exchanges fair and manageable.
What if the prompt doesn’t resonate with me?
Skip that month. Wait for a prompt that speaks to you. There’s no pressure to participate every single month.
Can I suggest a prompt?
Yes! I’m always open to suggestions. Email me your ideas and they might inspire a future month’s theme.
Technical Questions
When are the deadlines each month?
1st: Prompt sent to paid subscribers
10th: Letter submissions close
15th-18th: Exchanges delivered
25th: Published archive sent to all subscribers
What if I don’t receive my exchange email?
Check your spam folder first. If it’s not there, email me and I’ll resend it immediately.
How do I submit my letter?
You’ll receive a welcome email with a link to a simple form when you become a paid subscriber with each prompt. Fill it out and submit by the deadline.
Can I edit my letter after I submit it?
No. Once submitted, it’s final. Take your time before you hit send.
Will my letter be published without my permission?
Never. On the form, you’ll be asked explicitly if you consent to publication. If you don’t respond or say no, your letter stays private.
About the Project
Who runs Dear Stranger?
I’m Dakkota. I created this project out of love for letter writing and a belief in its power for mental health and human connection.
Why did you create this?
I wanted to bring back the lost art of pen pals and letter writing for the modern world. Anonymous letters create space for radical honesty—truths we’d never speak if we thought someone might know who we are. In a time when we’re more “connected” than ever but often feel alone, I wanted to create a space for real connection through vulnerability.
How are letters matched?
I read every submission and pair them thoughtfully based on emotional tone, theme, and sometimes matching preferences you indicate in the form. It’s not random—it’s intentional.
What if this grows too big for you to manage alone?
Right now it’s just me, and I can handle up to about 50 paid subscribers manually. If we grow beyond that, I’ll invest in automation or bring on help—but the heart of this (reading letters, thoughtful matching, protecting anonymity) will always be handled with care.
Still have questions?
Send me a message. I read everything and respond to everyone.
This space exists because of the people brave enough to participate.
Thank you for being here.
With love,
Dakkota