“You’ve got mail.”
For most of us, it’s just a notification.
For someone in prison, it can be the highlight of their entire week.
Ever wondered how this all started? Who first decided to send a letter to someone behind bars, not out of duty, but out of compassion?
At A Way Out Pen Pals, we’ve seen how a simple envelope can restore someone’s sense of self. But this movement didn’t begin overnight.
Let’s take a look back at how prison pen pal programs first began and why they still matter more than ever.
How It All Began: When Did Prison Pen Pals Start?

The idea of writing letters to inmates isn’t exactly new, but organized prison pen pal programs really began taking shape in the late 20th century.
In the 1990s, a small school program in West Virginia known as The Prison Project got students to exchange anonymous letters with people serving life sentences. One student wrote to an inmate called “Frodo,” who replied with honesty, humility, and a desire to be seen beyond his crime. These letters shattered stereotypes and showed the raw power of human connection.
Soon after, online platforms like WriteAPrisoner emerged, giving inmates a way to post profiles and connect with people on the outside.
By the early 2000s, the act of writing to prisoners was no longer underground or taboo. It was a movement.
The Purpose Behind the Pen: Why People Write to Inmates

At A Way Out Pen Pals, we’ve seen it firsthand: people write to inmates for all kinds of reasons:
- To offer emotional support
- To create genuine friendships
- To stand up for restorative justice
- Or simply to bring hope into a place that desperately needs it
Writing to inmates in the past wasn’t about charity; it was about connection. And today? It’s a way to tell someone, “You still matter.”
Organizations That Helped Pen Pal Programs Grow

A Way Out Pen Pals
We’re not just here to pair strangers with inmates. We’re here to build bridges. Whether it’s your first letter or your fiftieth, A Way Out Pen Pals supports both sides of the connection, with resources, safety tips, and a community that truly cares.
WriteAPrisoner.com
One of the first major platforms where inmates could share profiles and receive letters. It opened the door (literally) to thousands of new connections.
Black and Pink
A support-driven initiative that matches LGBTQ+ inmates with allies for regular, affirming letters.
Prison Journalism Project
Started as a way for incarcerated people to share their stories with the world. In many ways, it’s the evolution of pen pal programs turning personal letters into published essays.
Real Stories, Real Impact
In a Medium article by a writer who exchanged letters with an incarcerated person for years, she writes:
“I thought I was the one helping. But over time, I realized his words were helping me just as much.”
That’s not unusual. We’ve heard the same from people writing through A Way Out Pen Pals, how it started as a good deed, and became a relationship that changed both lives.
The Psychology Behind It: What the Research Says
Writing letters isn’t just feel-good fluff. Studies show that inmate correspondence reduces isolation, improves behavior and gives people something to live for during incarceration. It supports emotional growth, reflection and even helps with reintegration after release.
Plus, it helps people on the outside develop more empathy, patience and perspective.
The Challenges No One Talks About
To be honest, not every prison pen pal experience is perfect.
- Sometimes expectations aren’t clear.
- Letters may take weeks to arrive.
- Miscommunication happens.
That’s why A Way Out Pen Pals is created on trust and transparency. We check every profile, guide every new member and offer support if things ever feel off. You’re never doing this alone.
What This Means for the Future (And You)
If you’re a startup founder, a writer, a teacher, or just someone who wants to make an impact, this is your chance to join something real.
We’re not just looking for people with time. We’re looking for people with heart.
Letters won’t fix the system. But they might heal the person.
And that’s where change begins.
Ready to Get Involved?
At A Way Out Pen Pals, we match people who care with those who’ve been forgotten. If you’ve ever wanted to do something that matters, this is your sign.
- Become a Pen Pal Today
- Read more inspiring stories
- Learn how it works
FAQs
1. When did prison pen pal programs start?
Organized prison pen pal programs began picking up in the late 20th century. But informal letter-writing to inmates has existed for decades. The real shift happened in the 1990s and early 2000s, when platforms like WriteAPrisoner.com made it easier for people on the outside to connect with those inside.
2. Why do people write to inmates?
People write to inmates to offer emotional support, build human connection, or simply be a friend to someone who’s often forgotten by society. Some are driven by a sense of justice, others by curiosity or compassion. At A Way Out Pen Pals, we’ve seen many beautiful, long-term friendships begin this way.
3. How do I become a prison pen pal?
It’s easier than you might think. You can sign up on our Get Started page at A Way Out Pen Pals, choose a profile, and we’ll guide you through every step. We also provide tips, writing prompts, and ongoing support so you’re never doing it alone.
4. Is it safe to write to someone in prison?
Yes, as long as you follow basic safety guidelines. Don’t share your home address (use a P.O. box or digital mail service), set boundaries, and trust your gut. We provide a full Pen Pal Safety Guide to help you feel confident and protected throughout the process.
5. What should I write about in my first letter?
Be kind, curious, and honest. Share a bit about yourself, like your interests, your favorite music, and what a normal day looks like for you. Ask open-ended questions to invite conversation. Avoid asking about their crime in the first letter. Let trust build naturally.
6. How often should I write?
That’s up to you and your pen pal. Some write once a week, others every few weeks. What matters most is consistency and sincerity. Even just a letter every month can mean the world to someone inside.
7. Can I email my prison pen pal?
Some prisons allow messaging through platforms like JPay or CorrLinks. Others only accept handwritten letters. At A Way Out Pen Pals, we’ll let you know what’s allowed based on the inmate’s facility, so you’re not left guessing.
8. What if I want to stop writing?
Life happens. If you feel the need to pause or stop, it’s okay, just be respectful. Send a final letter explaining your decision, and consider contacting us if you need help navigating that goodbye. We’re here to support you, too.