Prison Penpals: Who Writes and Why?

Having posted recently on this blog about the problems prisoners can face in keeping in touch with family and friends while they are in jail, I thought I should write something on the subject of prison penpals. These can really be a lifeline for prisoners who don’t have any close family or friends of their own. Just receiving an occasional letter from the outside world can make all the difference to someone who is struggling with life inside.

Although the whole prison penpal thing isn’t yet as developed in the UK as it is in the USA (where there are numerous websites listing cons requesting penpals such as ILoveMyInmate.com), it is still a growing phenomenon in our prisons. I know a large number of cons who do write regularly to their correspondents, some of whom they have never actually met in person. 

Typical US penpal ad

Sometimes these penpals are friends of friends, or even female prisoners in women’s nicks. Others are involved in various prisoner support groups, religious organisations or just make contact through online websites similar to the US versions.

In general, I’m all in favour of anything that provides prisoners with a window on the outside world and a bit of normality in what can be a very dark, depressing and loveless environment. Having a regular correspondent can also improve cons’ writing skills, as well as their motivation to learn.   

Years ago I was involved with an international charity that matched prisoners on US death rows with penpals. For several years I wrote a couple of times per month to a con who was in a prison down in Florida. He was an entertaining correspondent and I did learn quite a lot about the US penitentiary system from him. We also had a shared interest in English literature and I was able to order paperback books for him via Amazon.com. We’d both read the same book at the same time and then compare our views and reactions to it in our letters. I really enjoyed writing to him and I like to think that our correspondence made his existence on death row a little more bearable and less isolated.

Sadly, his appeals ran out, his time came and he was executed by lethal injection. I still have a collection of his letters that were written around 12 years ago, including the last one he sent me the night before he was put to death, in which he thanked me for my friendship and support. Obviously, back then I never imagined that I’d end up in the slammer myself. It’s a strange old world.

So I do appreciate how important having regular correspondents can be, especially when prisoners have no-one else with whom they can communicate. However, there can be potential perils and pitfalls for the unwary. 

I was reminded of the problems with prison penpals when I was reading one of the latest letters on the excellent Prisoners’ Families Voices website. I’ll share it because I think this is an instructive story of the sort that will be familiar to anyone who has served a jail sentence, but which may come as something of a surprise to those who haven’t had any direct experience of prisons or prisoners.

The writer of the letter explains that she made the decision to break up with her then partner who is serving a lengthy stretch inside and told him this during a visit. She goes on to observe that her ex recently informed her in a letter that he has now met another woman who has become his penfriend. 

In this letter he also let her know that this person is sending him money and ‘looking after him’. However, she relates that her ex-partner then goes on note that he has no intention of settling down in a relationship with the woman he is writing to, but would “jump at the chance” to get back together with her (his ex) when he is released. And thereby hangs a tale!

Writing in search of love or...?

This phenomenon will be only too familiar to many women who have developed a penpal relationship with a bloke who is in the slammer. For those on the outside, writing to a con they may never have actually met is seen as a slightly edgy thing to do. There may even be a frisson of excitement in corresponding with a self-proclaimed ‘bad boy’ who has some tattoos and a bit of attitude. 

Prison, by its very nature is a closed world and people can become very curious about what really goes on inside. Maybe that’s why so many people read this and other prison blogs.

However, there is also a potentially romantic element to having a boyfriend in the nick, particularly for females who are a little bit – how to put this politely? – needy. Having a boyfriend who is in jail at least means that his penpal girlfriend knows where he is on a Saturday night. He won’t cheat on her – at least not with another woman – while he’s inside and the fact that she holds the purse-strings also gives her a degree of power over him. It’s her decision whether she sends him a regular postal order or not. The relationship can soon become one of mutual dependence: romantic, as well as financial.

A weekly postal order can make all the difference

The key problem is that a sizeable number of cons are highly manipulative people. Those that don’t have close family members willing to provide financial support have limited options when they are in prison. Having a penpal who is willing to provide the readies for burn (tobacco) and other essentials is a prize worth having. If she (or he – believe me, some cons aren’t that fussy) keeps that all-important cash flow coming, then his letters from prison will continue to drop on to the doormat.  

Understandably, a great many cons are also sexually frustrated. Having a regular supply of explicit letters from a female correspondent is a massive bonus, as is having a few candid photos from time to time. Of course, there is a limit to just how sexually explicit prison mail can be, but the bar is actually pretty high before a letter will get blocked. 

While working as an Insider (peer mentor) I’ve been asked to read letters to cons who have problems reading and I’ve been quite amazed at what routinely gets past the censor, including some of the photos wives, girlfriends and female penpals have sent in. Really racy ones might get passed round between mates in order to spice up those moments when a prisoner manages to get some special time alone in his cell… if you catch my drift. 

Some do find true love with cons

I have known some cons who build up quite a ‘stable’ of female penpals, often in addition to having a wife or regular girlfriend at home. One young drug dealer I got to know quite well in a B-cat nick was running four relationships simultaneously: his partner, with whom he had two kids, as well as three unsuspecting female penpals who each thought that they were in exclusive contact with him and who believed they were romantically involved. 

All four women were sending him a monthly postal order and the cash, which totalled much more than he was allowed to spend each week on the canteen, was mounting up in his prison account. He was completely shameless about his activities, although he did ensure that he wrote a loving thank you letter to each one in response to every letter – and postal order – he received.

Now, it is also true that some prisoners and their penpals do form serious relationships that continue after release. However, for every story of true love, I would guess that there are another half-dozen that are doomed from the start, mainly because – as in the case described above – the con really isn’t romantically involved beyond breaking up the boredom of prison life by writing letters and, of course, waiting for the arrival of those loveable little postal orders that make life in the slammer so much more bearable. And as the cynical American writer Dorothy Parker once observed, the two sweetest words in the English language are “cheque enclosed”. I wonder if she ever wrote to a con.