Free Prison Pen Pals: FAQs

If you're willing to suspend your suspicion for a moment, I'd like to tell you about Thomas, a friend of mine who is incarcerated in a prison in California. While randomly surfing the web two years ago, I stumbled across a free prison pen pals advertisement and decided, mostly out of curiosity, to see what it entailed. Reading through a mix of ads - some tragic and some hopeful, some deftly worded and some nearly incomprehensible - I came across Thomas. He seemed like a bright guy who just wanted a friend - no legal help, no money, no long-term relationship - just someone with whom to exchange letters.

Strangely compelled (and needing a reason to break in a stationery set that I almost regifted one Christmas), I wrote a short letter to this inmate and invited him, basically, to tell me his life story. As I dropped the letter into the mailbox, I felt nervous and silly but justified and intellectually curious. A few weeks later, I got a long, sincere reply from Thomas. Since then, we've exchanged letters once or twice a month - an enjoyable experience for me and apparently for him as well. Some people react with skepticism when I explain that I have a pen pal who's in prison, and others express admiration at my willingness to reach out to an often forgotten population. After all, many of these people will rejoin society one day (some sooner than others), and I'd like to think that some good comes out of my correspondence with Thomas and the handful of other people behind bars I've befriended.

If you're still reading this, I'd like to share my responses to some frequently asked questions about free prison pen pals.

Free Prison Pen Pals: Why do it?
These are some of the loneliest people in America. They need support and hope, and your letters can provide that. Based on my experience, I can vouch that exchanging letters with an inmate can be rewarding. You don't have to relate 100% of their experiences or vice versa for the connection to be meaningful.

I can remember one particularly bad day last year, when I came home from work pissed off at the world and cranky about everything. That day, I got a letter from Thomas, and it really put my day into perspective and lifted my mood. First, it reminded me that I enjoy remarkable freedoms that I ought not to take for granted. Second, it reminded me that I have a role to play in social betterment - that I had someone I'd never met who was, in a way, looking up to me as a sort of role model. While I can't promise that you'll have the same meaningful experience I have had with a prison pen pal, I'd say it's worth a shot considering the minimal sacrifice of time involved.

Free Prison Pen Pals: Why would I want to befriend a criminal?
Well, if you're that flippantly judgmental about people's mistakes, maybe it's not for you. But if you want to hear life stories, if you want to be a positive influence, if you believe that people can mend their ways….then a prison pen pal is something to pursue. The sites I have used also tell prospective pen pals, whenever possible, what crime the inmate is incarcerated for and how long they're expected to be in prison. If you'd rather not correspond with a convicted murderer, you might be able to find someone who was guilty of a less violent (or even a nonviolent crime). There are white collar criminals on these lists, and some of them are incredibly bright people who've just done really stupid things. In the end, however, you control the experience.

Free Prison Pen Pals: Aren't these guys just scamming for money?
Not surprisingly, some of the men on prison pen pal sites are con artists who mask their intentions. After all, their questionable judgment has already landed them in prison. If you browse the ads, you'll notice that some of the men are sensitive to the issue and try to assure you up front that they just want a friend - not financial support or someone to house them after release. That said, the only way to know is to correspond with someone. They can't exactly compel you to do anything you don't want to do.

Free Prison Pen Pals: Are these men looking for platonic friendships or do they want something more?
Many of the guys just want a friend. But many are also looking for a potential relationships for after their release. Usually, they tell you up front in their ad what they're looking for, who they'll reply to, etc. In my case, I made sure I didn't write to prisoners whose profiles said things like "Ladies only!" or "I want someone to build a life with." Use your judgment and don't get involved with a guy who's looking for a spouse if all you want to do is be a supportive friend.

Free Prison Pen Pals: Writing to people in prison…how safe is that?
Exchanging letters with a prison pen pal is quite safe, as long as you use sound judgment. After all, the guys are sequestered away from society in a penitentiary. When compared with meeting a chat room friend in person, this is arguably much safer. Granted, most of the men do get out of prison eventually, but all they'll really have is your name and address unless you share additional information. It's really not much of a risk compared to the surprising satisfaction you derive from being a friend to someone in need.

Free Prison Pen Pals: What do you talk about?
Anything you want to. Spending most of their days alone, these guys have time, time, time. Most of them will tell you the (often) compelling story behind their crime, how they are working toward rehabilitation, etc. Thomas told me that, at his prison, he's only allowed to read two books a week and he has to force himself to read slowly just to make them last. A letter from a pen pal might be the one thing that makes their day stand out from every other day that week. This captive audience (sorry for the bad pun) will likely talk to you about anything you choose….though of course the communication should be a two-way exchange. I've talked with Thomas about everything from pop culture and politics to religion and philosophy. If you find the right inmate, you can be intellectually stimulated - an unexpected but welcome delight.

Free Prison Pen Pals: What about religion? Can I mentor someone spiritually?
Some inmates turn to spirituality while in prison and are looking for people on the outside with whom they can correspond or talk about the Bible (for example). If you feel it's your duty to help another person explore his or the faith from behind bars, you may want to do that. Some inmates specifically state that they're looking for someone who is Christian or someone who can explore God with them.

Free Prison Pen Pals: Are female pen pals available?
Though far less common, female pen pals are indeed available. The problem is that you'll have fewer inmates to pick from, and this makes sense based on our nation's crime statistics.

Free Prison Pen Pals: Okay, I want to give this a try. How do I find free prison pen pals?
While some sites do require a fee (don't use those!), most are free. I think that www.writeaprisoner.com is the best-organized site, but www.prisonpenpals.com and www.inmate.com are also worthwhile. I'd urge anyone considering a prison pen pal to ignore the corny marketing on some of these websites and just focus on reading ads and responding to the very few people who, in your opinion, seem worthy of your correspondence. Also, know that some sites will allow you to send an email, which prison staff will print out and give to the inmate, saving you a stamp. Even though they can only write back via snail mail, it's a feature of which you should take note.