So you have a prison pen pal, and you are not sure what to write, how to write it or how much information to give. This is a good question. Obviously, you would need to exercise some precautions. You would also need to make sure the relationship is mutually beneficial. At this point, you would need to determine just what purpose you want the relationship to have. The excitement from writing a prison inmate will pass. When it does, it would be helpful to have something with which to replace it, something substantial.
Learn from them. Gather pieces of information, even seemingly useless pieces of information, about your prison inmate. Their life experiences can help and guide you in your own life. In this manner, you can avoid making the same mistakes as someone else. Also, having a prison pen pal can help you become a more well-rounded individual, because it opens up your mind to the possibility that not everything is in black and white and not everyone is to be judged harshly or in ultimate terms.
Have a beneficial influence on them. You can bet that it is sometimes helpful to know “people” and that prisoners know lots of “people.” In order to gain clout with them, have a beneficial influence on their lives in return. Send them books on a regular basis, and do not stop doing this in a year or so, but keep sending them reading material. You will have to send them these books through the vendor, so have them mailed to your inmate through Amazon.com or BarnesandNoble.com, or a similar book source. Do not send them books directly, for that will be rejected by the prison and considered contraband.
In addition to sending them books once or twice a month, send them beautiful letters of warmth, love and friendship, describing all of the nice warm homey things which occur around you. Tell them if you have just made fresh bread or about the funny incident with the kids and their playmates. Send them funny or dirty jokes you have heard and include them in your life in this way.
Stay safe when revealing information. If your prisoner is not a family member, you need to stay safe when revealing information about yourself and your family. If you have a post office box, use this rather than having the mail sent directly to your house. Do not send photos which reveal street signs or landmarks which can identify the location in a city or a particular house. Even when talking to a family member, keep financial and bank information out of your letters, because these can be found by other inmates or prison staff and used against you or your prisoner.
Do not send messages back and forth between your inmate and someone else. Do not conduct business deals for your inmate. And do not be a drug mule when visiting them.
Having a prison pen pal can be so beneficial and rewarding, especially since these guys are sometimes just big teddy bears wrapped in a little barbed wire. Allow this pen pal relationship to enrich your life, and be sure to enrich their lives in return.