Writing a letter to someone in jail should include happy or humorous reminiscences, encouragement to participate in prison programs, encouragement regarding the future and expressions of love and caring. In jail, it is common for prisoners to feel abandoned by friends and family on the outside.
It is sometimes difficult to start a letter to someone in jail. Try reminding the person in jail of an enjoyable shared experience. Not only does this let the person know he is missed, it also allows him to think of something outside of his confines.
Adding a new and positive outlook in a letter which is always encouraging, because it lets the prisoner know that they can make new choices in the future. Many prisoners will find it difficult to think about the future, so it is always a good idea to encourage them to think about what the future could be like, as well as to participate in education programs while in prison to build toward that future.
When writing to a prisoner, it is important to remember that prisoners' mail is always inspected. Items not allowed in prisoner mail typically include photos, nude pictures, money, checks, cards or any powders or liquids.