Prison Pen Pal: Rules of Engagement

Do you know someone who has ever thought about becoming prison pen pals with an inmate? Depression and loneliness are serious matters for inmates, especially for those that don’t have supportive families. They may have repeated a plethora of criminal activities and their families have shunned them. They may have strict families that despise their criminal activities, even if it was nonviolent. They may have a neglectful family or just never been close to their family members. For those that don’t have a family to go home to, the risk of returning to prison is greater. Having a prison pen pal may be the only support they ever receive, and although a prison pen pal is good for a number of reasons and it is bad for so many more. 

There have been countless stories of prison pen pals who have taken advantage of their writing partners. There are even more stories about people who fall in love with prisoners based on their writing skills. Some even marry them! Most of the time it doesn’t end well – as in they are killed and sometimes even their family members are murdered too.

According to Psychology today,

Although many offenders do benefit from a kind word and a helping hand, those people who wish to assist (or acquire a more serious friend) should learn the behavioral red flags. Past violence is among the best indicators of future violence. So is a lack of remorse for harming others, a history of deception, a lack of respect for others, and a tendency to blame others for one’s own behavioral issues. Convictions for murder, sexual or physical assault, home invasion and crimes involving deadly weapons all foreshadow a dim future with such offenders. Often, they have poor skills for inhibiting impulses and for negotiating in relationships.”

prison pen pal


So if you know someone who has decided on this venture, give them my suggestions for becoming a prison pen pal. 



Be Careful
Many people believe becoming a prison pen pal is extremely dangerous. They are right, some people don’t want to change and will still try to prey on weak minds. There are stories of inmates selling pen pal information and running scams. There are stories of pen pals inviting felons to their homes and dying because of it. However, there some people who have done it and found good people to mentor. A guy says that he found a young adult who was convicted of vehicular manslaughter, He was a passenger of a friend who had almost done the same to him, but he survived. He sought someone to encourage and this is his advice.

“You need to be careful, some of these men/women are extremely smart and will try to exploit you so you need to background check on their crime before you decide to go into something like this. You also need to be committed to keeping in touch as these people have barely any or no contact with the outside world so they can be in a bad place so someone who writes [and] then stops can have a huge impact on their mental health.”

Never Give Personal Details or Send Money or Pictures
The point of a prison pen pal is to make a connection and provide outside social interaction for someone who is devoid of it. Although getting to know someone is obviously done by sharing information, your home address, the names of your children and family members, and where you live/work/worship should be off limits. You also shouldn’t do them favors such as researching or contacting people. Instead talk about aspirations, inspiring people, goals and dreams, and maybe even politics. Use a P.O Box when mailing letters as some inmates have ruthless bunkies that would love to take advantage if your prison pen pal doesn’t try it themselves. If you are feeling like you want to share personal information, write it on your social media page instead. In fact, if you are feeling like you need to share personal information, stop reading and writing for a few weeks and get yourself together. If your prison pen pal asks you personal information, don’t feel pressured to answer it. It’s a letter for goodness sake! It’s not a face to face conversation, so it’s much easier to either ignore it or set boundaries.

A Real Human Connection
You want to find someone who is in need of emotional support, but not someone who is needy. Change prison pen pals if you receive letters with sob stories over and over again. After you have offered them sound advice on how to acknowledge their wrongs and suggest ways to move on and better themselves, there isn’t much you can do unless you’re a licensed psychologist. Someone who is truly remorseful will bring up their wrongdoing every now and then, but they will not play the victim or make you pity them. The objective of exchanging letters is to communicate with someone who needs a normal human connection to the outside world. I previously mentioned that some don’t have families that care or visit them anymore. There really are inmates in need of human connection, but sometimes it can be a needle in a haystack. I read on the New York Post’s website about a woman who befriended a murderer and here’s what the killer said, “makes me feel like not everyone has given up on me. In a world so quick to shun people over a bad decision, I’ve found a one-of-a-kind connection with a woman who lives nearly 8,000 miles away”. The difference here is that his crime was drug-induced, however, who is to say that once he gets out, he will continue on a good path and never do drugs again?

If you ask me, there are better ways to help inmates that want change. Here are a few of the resources I found that actually have proven aid for prisoners.

Free Minds Book Club & Writing Workshop

This organization is dedicated to changing the lives of inmates through reading and writing. I don’t mean teaching inmates to read and write, but they encourage emotional expression through writing and reading poetry. They offer feedback on written works and have sessions where their interns write back to inmates. If you need someone to write to, this organization may be the best place for you because you will have accountability to write good things and not become romantically involved.

Support Wrongful Conviction Cases

Northwestern Pritzker School of Law has a clinic in which they help those who have been wrongfully accused. If you ever wanted to find someone to write to, these people may be a better choice than a random person on one of the sites below.

Send Books Through Amazon

The Chicago Books to Women in Prison has an Amazon wishlist full of books that inmates have requested but are rarely donated. This nonprofit organization sends books nationwide to women in jail and only ask for your name and email address.

Post Bail for the Holidays

The Brooklyn Community Bail Fund is a project that seeks to intervene on behalf of those that are too poor to post even the smallest amounts of bail. The work with other organizations nationwide to bring awareness to this issue. You may have heard of them when they posted bail for a large group of mothers on Mother’s Day. If you’re concerned about them making their court dates, rest well knowing that 95% of their clients make it back to court.