I have been corresponding with and visiting a man on Death Row at San Quentin State Prison in California. Through this relationship I have met other prisoners and numerous people on the “outside” who write and visit them. For the most part, people on the outside find these experiences very rewarding. However, sometimes there are communication glitches which can lead to misunderstandings. My purpose is to provide information to prisoners from the perspective of “those on the outside.” This may help in forming positive, successful relationships.

How Do Outsiders Feel?

If an outsider has no experience writing to people in prison or visiting them, s/he will feel anxious and uncertain about beginning a relationship and wonder the same things you wonder: “Will s/he like me? Will I know what to do? Will I offend the person? Will we be comfortable with each other? Will I know what to ask?” So, in interacting with the outsider, keep in mind that this person is probably nervous, anxious, and challenged by the uncharted waters. You can help by easing the process as much as possible.

Pen Pals

Usually the pen pal will write you first. I’ve matched several people on the outside with prisoners, and every time they agree to write, the first question is, “What in the world will I say?” Writing that first letter can be a formidable task. I suggest that the person write a one-page letter with some basic information about him/herself (gender, age, marriage status, occupation, number of kids) and tell why s/he has chosen to write someone in prison. I suggest that the person describe any and all important, basic ground rules. For example, a single woman writing to a single woman in prison might make it clear from the beginning that she is not interested in any romantic involvement with a prisoner. I suggest that the pen pal ask the prisoner if he/she would like to correspond and see if writing each other “works.” This way, the prisoner has an out if the potential pen pal is obviously someone, he/she would not want to write.

Getting that first letter from you is really exciting for the outsider pen pal. Thank the person for writing. You can respond by providing some basic information about yourself, such as sex, age, how long you have been in prison, height, number of kids, where you’re from. Pen pals usually don’t know why you are in prison, and they don’t (or shouldn’t) expect to know. Don’t feel any obligation to get into this at all. If the pen pal asks about your conviction, crime, innocence/guilty status, you can simply write back that “you aren’t comfortable writing about it.”

A really effective technique in corresponding is to respond to something specific that the pen pal has written to you. For example, if s/he writes about playing bridge, you might respond with some comments about bridge, either that you play it or that you don’t, or you know someone who plays it, or you play a different card game. It is important to avoid writing letters that are just about your life, your struggle, your issues. Even though life on the outside is obviously much easier and better, there has to be a balance between your life and the outside pen pal’s life. You must show genuine interest in the pen pal.

A sense of humor is essential. In every letter, try to write something that is humorous. My pen pal and I make lots of jokes about being in prison, and I have started this ongoing joke between us where I pretend that I’m Martha Stewart, and I write a magazine column called Martha

Stewart’s Prison Living.

Sending pictures back and forth easily adds to the relationship. If you have original pictures you want to keep, ask your pen pal to get a color copy for him/herself and send the original back.

Tell your pen pal very early on about the prison policies for reading mail and about what is or is not allowable to send in the mail. Knowing the rules will ease anxiety. Indicate how long it takes for you to receive the other person’s letters.

You really can’t thank these people too much. If you err on any side, make it the side of gratitude. Don’t make any demands on your pen pal or write things which sound like “orders.” For example, one prisoner wrote his pen pal that in responding to a letter she had failed to mention the date and that from now on she should always do this. This was not well received by the pen pal.

Pen pals are precious connections to the outside world and must be treated gently. Don’t overstep any bounds such as mailing something they aren’t expecting. If you want to send them something other than a letter, check it out with them first.

As the relationship develops, your pen pal may ask questions which provide an opportunity to mention things you need that could be sent. For example, you pen pal may ask if you have money and how you may acquire it. In answering this question, you may want to explain how people on the outside can send you money. If your pen pal asks about sending you things such as food or books, you have an opening to say what you are allowed to receive and how the system works. Keep in mind that your pen pal probably has absolutely no idea how prison works and is completely naive. If your pen pal indicates a desire to send you money or a package, send complete instructions so the enterprise will be a success. No one wants to fail in these endeavors. Keep thanking them!


Visitors have an extra element of guts and deserve special effort on your part. If your pen pal indicates a desire to visit, get the most recent prison rules about visitors and send that to him/her. Share everything you can learn about what happens to visitors — what they have to wear, what they have to fill out, the metal items they have to take off, whether they must pass through metal detectors, whether guards touch them during the process, what they can bring into the prison, whether you will come out first and wait for them or whether they will be there first and wait for you. Where will they meet you? Will you be able to touch each other or will you visit through glass? How long can you visit with each other? Will your conversations be recorded? Is food available, and will you be eating together? What time should your visitor arrive at the prison?

What days can people visit? The more you tell your visitors, the less anxiety they will have. Anxiety about visiting is what usually prevents people from doing it, so nothing is more important than your work to minimize anxiety.

The first time your visitor actually comes to the prison, inform him/her about the rules in the visitor’s area. For example, at San Quentin Death Row visiting room there are blue plastic chairs and a few tables. Only the attorneys can use the tables. Visitors are supposed to sit down and keep their hands in sight. No “excessive” demonstration of affection is allowed. The prisoner cannot handle money for the vending machines. Tell your visitor about these prison rules. In addition, there are “unwritten” rules in this environment, which may be very foreign to the visitor. For example, as San Quentin visitors stay almost exclusively with “their” prisoner. There is little conversation or interaction with other visitors or prisoners. Visitors are not supposed to ask questions about prisoners’ cases, status, or crimes. There is a very big “mind your own business” atmosphere there. As your comfort level with each other increases, tell your visitor about the “unwritten” rules. This is a different world and often seems crazy to the visitor, who doesn’t want to make mistakes, but may not be able to figure out the rules.

Tell your visitor there may be times when people arrive at the prison and find it “locked down.” Indicate whether visitors may be asked at some point to submit to a strip search. Discuss what should happen if your pen pal is expected for a visit, but can’t make it for unforeseen reasons. Will you call to find out what happened? Will your pen pal write you to tell what happened? The more knowledge you provide to your visitor, the more comfortable and confident he or she will feel about visiting.

One more thing: Visitors are often hassled and made to put up with changing rules and a basically chaotic system. They deserve much appreciation and gratitude for the love and concern they demonstrate in continuing to make this journey to visit you.

Much luck in your pursuit of connections to the outside!

The Cell Block is America’s #1 prisoner information and entertainment company. Two great books about writing letters and getting pen pals are The Art & Power of Letter Writing for Prisoners, Deluxe Edition, by Mike Enemigo, and Pretty Girls Love Bad Boys: An Inmate’s Guide to Getting Girls, by Mike Enemigo and King Guru. You can learn more about us and all our books at Be sure to subscribe to out blog, The Official Blog of The Cell Block, where we provide you raw, uncensored news, entertainment, and resources on the topics of prison and street-culture, from a true, insider’s perspective.