Starting a Letter to an Ex-Prison Inmate: Tips and Considerations

Starting a letter to someone who has been in prison can be a sensitive task, especially if it's been a while since you last spoke. Armed with warmth and sincerity, your letter can serve as a bridge to reconnect with someone whose life has faced significant challenges. Here are some guidance and tips to help you craft your message.

Warm Greeting and Personalization

Begin with a friendly and warm greeting. Use their name to personalize it and make the tone personal and earnest. For example:

Dear [Name],

Acknowledge the time that has passed and express that you’ve been thinking about them. This shows you care:

I hope this letter finds you well. It’s been a while since we last spoke and I’ve been thinking about you a lot. How are you holding up during this time?

Let them know why you’re writing. You might want to reconnect, share updates from your life, or offer support:

I wanted to reach out and see how you’re doing during this time. I hope you're managing to stay positive and find a path forward. I'd love to hear about any changes in your life since we last talked.

Using Online Resources

Before you start writing, you can visit inmate profiles online. Websites like can provide you with a little more insight into the person:

When you look at these profiles, remember that they are often paid for and edited by outsiders. The information might not always be entirely accurate or up-to-date. Be skeptical of any information provided and avoid sending money or sharing your address with anyone:

I notice some of the inmates on  say they are interested in friendship. Be cautious and practice utmost diligence.

Probing Caution

While you can be kind and considerate, it's important to proceed with caution. Consider the following precautions:

Do not send money or valuables: Inmates could misuse this information to harm you or others. Be wary of personal information: Don't share your address or personal details that can be misused by perpetrators. Adjust your tone based on your relationship: If you have a deep connection, tailor your approach accordingly. Stay vigilant and informed: Keep yourself updated on any safety measures or potential risks.

For example, if you knew a man from your church who used to send religious materials to prisoners, his kindness and faith overruled his common sense. He was eventually found dead, leading to a tragic and cautionary tale:

I knew a man from my church who used to send religious tracts and materials to people in prison, thinking he could witness his faith to them. He was kind, but he met a young homeless man needing a place to stay. He allowed the man to stay with him for a few days, and then he was found beaten to death. The police made an arrest, and the other guy was sent to prison. I attended his funeral and the sentencing of the other guy. We talked about this a great deal and the kindness of that 74-year-old man. However, his kindness overruled his common sense.

Remember, being compassionate is important, but it is equally crucial to be cautious and protective. You can make a positive difference while ensuring your safety and the safety of those around you.

Conclusion

Writing to someone who has been in prison can be a powerful act of kindness and support. By being thoughtful, cautious, and informed, you can help rebuild relationships and support someone who is working to rebuild their life.

Key Considerations:

Warm and personal greeting Acknowledge the passage of time Share your intentions for writing Be cautious with information and exchanges Stay informed and vigilant