How to make the most of your pen pal relationship with an inmate

How to Make the Most of Your Pen Pal Relationship with an Inmate

Writing to an inmate is a great way to show support and keep in touch while they’re behind bars. While there may be rules and regulations that you need to adhere to, by following them your letters will still be meaningful and appreciated. Before reaching out, make sure that the inmate you are communicating with is allowed to receive mail. Check out their facility’s policy by mail; it is important to get this right so your letter does not come back undelivered.

Additionally, it’s possible that the facility requires you to register as the sender of the letter for them to pass it along. Don’t use any language that could be interpreted as suggestive or disrespectful.  This could result in your message being rejected altogether. Most jails frown upon mentioning contraband items or suggesting illegal activities within your communications as well.   So its a good idea to avoid saying words like “drugs” or “guns”. Keep things positive and light, ask how they’re doing and what their goals are.  Let them know someone is thinking of them.

Learn about the inmate’s background and what led them to prison

Learning about an inmate’s background can provide insight into why they are in prison.  Plus, you can learn the circumstances that led them to their current situation. Contrary to popular belief, there is no one-size-fits-all reason for incarceration. Every case is different, and the stories behind everyone is significantly different.  However, they are usually heartbreaking to mind-boggling.  Before judging inmates for their actions, take a step back.  Attempt to understand their past experiences and what led them on this path.  After doing so, we can gain a better understanding as to how complex all our lives can be.

Send letters that are positive, uplifting, and encouraging

Writing a positive, uplifting, and encouraging letter is one of the best things anyone can do for a friend or family member.  By expressing your heartfelt thoughts through a letter, you can make the recipient feel special.  In addition to that, you’ll also brighten their day! We all need that extra dose of kindness from time to time.  Having it come in the form of a handwritten letter makes it so much more meaningful.  Plus, sending physical letters is an eco-friendlier alternative compared to electronic contact!  So don’t forget to spread some love next time.  Penning such letters may be an old tradition but never underestimate its power.  It reminds us how much we care about each other.

Avoid discussing topics such as crime or violence

When it comes to conversations, it is always best to keep things as positive and upbeat as possible. Instead of discussing topics such as crime or violence, shift the conversation towards something more cheerful and lighthearted.  Ask about family, hobbies, favorite books, or movies.  Anything that allows you and your conversation partner to connect on a deeper level.  Taking the dialogue in this direction will create a sense of mutual understanding.  This builds friendships that can last much longer than surface-level conversations.


Send gifts (within prison guidelines) that show you care about the inmate

The holidays can be a difficult time for those in prison.  Sending a gift to a loved one incarcerated can make their day brighter.  There is nothing more meaningful than showing you care.  While they are away it reminds them that they have someone on the outside who loves and supports them. Before thinking of what kind of gift to give, you need to check with the facility in question for any prison guidelines as gifts may vary from one institution to another.  Common permitted items include books, magazines, prepaid phone cards, cards, and stationery. You could also buy them some items to make their stay more comfortable.  This can include such things like clothing or toiletries.  Whatever it is, your gesture will make all the difference!

Keep in touch even after release from prison

Staying in touch with someone who has been released from prison can be a powerful way to influence their success.  Without a doubt, this  helps them transition smoothly back into the community. Not only is this beneficial for the individual, but it also creates a more cohesive society overall. Maintaining good relationships can help released individuals with finding affordable housing, suitable employment opportunities, and more. It’s an especially important approach to take if you were close before incarceration. A friendly reminder of your ongoing support could make all the difference in how successful your friend or family member is once they’ve re-entered society.

Show your support for their rehabilitation efforts

We all want our community to be a safe and healthy place for everyone. One way we can achieve this is by showing our support for those who are taking steps towards rehabilitation. Understanding that everyone deserves an opportunity to make positive changes in their lives, being supportive of those measures can help make an individual feel encouraged throughout the process. Everyone makes mistakes and it’s important that we recognize this and help when needed so others can be active and productive members of society. Showing support is a great way to spread a message of compassion, acceptance, and unity in our communities!


A pen pal relationship with an inmate can be a rewarding experience for both parties involved. You can help brighten someone’s day, provide support and encouragement during a difficult time, and even make a lasting friend. Just remember to keep the focus on positive topics, show your support for their rehabilitation efforts, and stay in touch even after they are released from prison. Ready to start your own pen pal relationship? Visit our website today to get started.