HeyJaredDear Stranger
Anonymous letters between strangers who will never meet. Every month, write what you've been holding and receive someone else's truth. No names. No judgment. Just honesty.
- Indexed issues, last 90 days
- 4
- Latest publication
- Sep 30, 2026
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- Earliest in this view
- Aug 1, 2026
Latest issues
October Letters: The Masks We Wear (opens the original)
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A small note before this month’s promptA few things are changing, last week I ran a poll, and 43% of you said the reason you weren’t taking part in the monthly letter exchange was that $8/month was too expensive. I heard you.<source type="imag
Poll Email - Why Haven’t You Upgraded? (opens the original)
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Hey,I’m trying to understand something.A lot of you read the Dear Stranger letters which is great. But very few of you upgrade to write your own and be part of our monthly anonymous letter exchange.I’m curious why. Please pick the one that resonates most:Your answer helps me build something better.—DakkotaDear Stranger is a reader-supported publication. To receive new posts and support my work, consider becoming a fre
September Letters: The Relationships We Stay In (opens the original)
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Dear Stranger,September is here.This month’s prompt is about the relationships we hold onto for the wrong reasons. The ones we stay in because of guilt, fear, obligation, or habit. Not because we want to. Because we feel we have to.Why do we stay? And what would it cost to leave?September Prompt“Write about a relationship you’re staying in—romantic, friendship, family; for the wrong reasons. Why do you stay? What would it cost to leave?”Maybe it’s a romantic relationship that stopped working but
August Letters: What You're Too Ashamed to Want (opens the original)
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Dear Stranger,August is here.This month’s prompt is about desire. The kind we’re ashamed of. The things we want but feel wrong for wanting. Success. Love. Attention. Rest. Freedom. The life that would actually make us happy, but we don’t let ourselves reach for it.Why does wanting feel like something to apologize for?August Prompt“Write about something you want but feel ashamed for wanting. Why does wanting this feel wrong?”Maybe it’s something practical. A promotion. Money. Security. But you fe
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