Browse websites that offer prison penpal ads until you find an inmate or inmates with whom you think you might enjoy corresponding. Some websites charge a fee for providing an inmate's address, but others do not. Most do not guarantee the accuracy of the information the inmates have provided about themselves. The penpal websites vary from the blatantly exploitative to the compassionate and intelligent. Find a website with which you are comfortable.
Verify basic information. Once you have an inmate's name, you can usually locate more information, including the nature of her charges and expected release date, through the state department of corrections inmate locator website or the federal Bureau of Prisons website.
Write her a letter introducing yourself. Some people prefer to use a P.O. box for corresponding with prisoners, but many use their home addresses with no problem. Keep your first letter light and casual.
Send a recent photo of yourself, and maybe a couple of other everyday sights such as your dog or pretty scenery. Send crosswords and interesting newspaper articles. Just about anything can help break the monotony.
Check with the department of corrections or Bureau of Prisons and find out what is involved in getting on an inmate's approved phone and visiting list. This will allow you to hear her voice, albeit at inflated collect call rates, and to meet in person when the time is right.
- Avoid pity, and if you cannot write to a woman in prison without judging her for her actions, don't write her. She has already been judged by society. Always remember that prisoners are human beings who made mistakes. Beware of declarations of passionate love or lust that come too fast, as well as requests for money. Commissary money can indeed make prison life more tolerable, and if you eventually wish to help in this way it is up to you. Some inmates, however, will string along a number of penpals-for-profit. Trust your instincts.