Underground Ministries

Prisoner Relationship, Resurrection & ReEntry


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There can be a quality of connection in written letters that often surpasses live conversation. Especially in an age of texts, tweets, emails.

Letters are where we in OPOP discover each other. It has been the foundation of my work with men in prison, and a place of quiet joy and honesty. Letters are where initial trust is built, which is essential for the road of reentry ahead.


Someone in prison is likely asking, Is this just a nice person in the community, or are these people who really care about the real me? Can I picture myself actually spending time with these people when I’m out?

Here’s some ideas to prompt the kind of letters worth writing—and reading. Where you hopefully see yourself anew, in this new correspondence. These prompts might spark better ideas. Go for it.

A Day in the Life

One way to introduce ourselves and discover each other’s lives is to simply describe a day in your life this last week. Both the basic routines, as well as something that made your week. Or a setback. Then ask our new friend to tell you about a day in his life inside. Our worlds are different in many ways at this point. Let’s learn. 

Why Are You Doing This?

Most everyone in prison is suspicious of other people’s motives. Especially for helping. So be as honest as you can: Why did you say yes to this OPOP experience? What motivates you? What fears or hesitations do you have? Honesty invites honesty.

A Turning Point

Those leaving the underground are very aware of the need to “change” their lives. Was there a point in your story when you faced yourself in the mirror and knew something had to change? Maybe you weren’t on hard drugs or in prison, but do you have a turning point (not just when you came to faith)? What struggles did you face? Then ask our new friend if he has a moment when he knew he wanted to change?  


What makes us laugh is often layered with story about us. What made you laugh this week? Share that. Ask our friend to share a story of what made him laugh this week.


Often people writing those locked up end up sharing something difficult in their stories that they’ve never shared with family or friends in church. This is powerful. A chance to share past or present struggles outside the “nice” bounds of church, not be judged by someone, and model to him our own imperfect humanity. See what happens.

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Here’s three words to keep in mind. They can help point us toward the connection we seek.


Most folks in prison carry a deep wound of abandonment. They’ve been dropped or forgotten repeatedly. We can either be part of the healing of this wound, or a deepening of it.

Consistency is more important than the content of your letters. It communicates to them that they are valuable. Not disposable.

Pick a day of the week—every other week. Put it on the calendar. Set aside this time. Enjoy it. This small discipline, this rhythm, might be a space and a gift you’ve deeply needed, yourself.


We belong to each other. We aren’t the helpers, they aren’t the project to be fixed.

You just being your authentic self invites another to just be themselves.

Beneath incredibly different life experiences, we find an equality of heart. The joy, the fun is discovering and enjoying this.


We don’t give advice, coach, correct, or mentor.

We may learn something that concerns us, or bothers us. The holiest stance is to be curious.

To wonder, with compassion, What’s the story that has brought this person to this belief, desire, or attitude? Do I have assumptions I could re-examine?

Curiosity frees us from judgment, and opens the gift of better questions and conversations.

Make sure you address your envelopes with their DOC number and your full name, on the front. Like this.

Make sure you address your envelopes with their DOC number and your full name, on the front. Like this.

Simple envelopes and paper only—typed or handwritten. Adhesive, glitter, fancy cards are rejected.

Simple envelopes and paper only—typed or handwritten. Adhesive, glitter, fancy cards are rejected.


JPay — Email in prison?


First and foremost, please understand that this is a commitment on your part to establish and maintain semi-long-term contact with a prisoner (through their release in less than two years). It can be devastating for a someone in prison to begin a relationship with someone on the outside and then have that relationship terminated prematurely because the person on the outside has lost interest or gets too busy to stay in touch.