Open Letter to Women in Prison Seeking Pen Pals


Dear Ladies,

If you’re a woman who’s tackled writing an ad to become a prison pen pal, seeking to meet (through correspondence) a new friend on the outside, this open letter is for you.

In earlier years, I’ve written several posts aimed to help those “civilians” gearing up from the other side as they prepared to write their first letters to female prison inmates. Topics included such things as learning how to read between the lines of a prison pen pal ad when choosing a prisoner, what to include in a first letter, and–just as crucial–what not to include.

However, none of those posts were designed to assist the inmate in writing her original ad, the tidbit with photo that the individual woman behind bars hopes will reach out and touch someone. I’ve realized that omission needs to be corrected.

True, few inmates may ever have the opportunity to find this page. It’s not like you’re all equipped with laptop computers and satellite connections that enable you to roam the Internet at will.

On the other hand, you never know. A friend or family member may see this and mail you a copy. That copy may speak to certain readers who have been down for a while. They may share it, and someone may one day realize it helped.

With that said, why am I writing this letter at all?

Simply put, dear ones, some of your online prison pen pal ads are really good and some suck rather badly. It’s a prickly proposition, trying to figure out how to present yourself in a positive light to total strangers. Based on the evidence, a few of you could use a little help with the wording.

I may or may not be able to provide that help, but I can tell you how certain ads impact me, a guy who’s been writing to women in prison for more than 17 years. My wife and I have corresponded with somewhere around 200 inmates, one of whom will be joining our household when her obligation to the State is completed in 2017.

Okay, so it says, "...met HIM," not HER...but when my uncle Bob emailed me this one, it was too good to resist.

Okay, so it says, “…met HIM,” not HER…but when my uncle Bob emailed me this one, it was too good to resist.

    Bad News First

Let’s take a look at a few lines from ads that really don’t cut the mustard. If you recognize yours, please don’t be offended. There are hundreds out there just like it, the basics obviously being copied and passed on from inmate to inmate as “the way to do it”.

Note: The “turnoff” words are emphasized by me.

–I am a stunning brunette who enjoys all that life has to offer. I am tall and lean with beautiful green eyes and olive skin.

–I am xx years old and absolutely gorgeous. Everything you could ever want and more.

–I have an intelligence to match my appearance….

–Yes, yes, I know what you might be thinking, brains and beauty all in one!

–…love to be spoiled, adored, and treated like a princess.

Okay, here’s the deal: If a man wants a woman who wants to be put on a pedestal and worshiped, there are plenty to choose from in the civilian population at large. And if he wants a woman who’s so into herself that she can’t wait to say, “Look at me! Aren’t I beauty incarnate?” Well, yes, there are plenty of those out here in the world, too.

In my opinion, the girl who labels herself as stunning, gorgeous, beautiful, etc., is simply shooting herself in the foot. If you have a photo posted with your ad, any potential pen pal will draw his own initial conclusions. If you’re dog ugly, homely as a mud fence, so hideous the doctor slapped you Mom when you were born, tooting your own horn in print is not going to change that. In fact, the reader of your ad will conclude you are, at best, vision impaired and can’t see what’s staring out at you from the mirror.

Conversely, if you are generally attractive, the average male is likely to think, “Wow. She really thinks she’s all that.” And then he’ll go on to the next ad because you just turned him completely off.

No matter where you live–i.e. inside a prison or out in the world–there are certain things it is unwise to advertise, to wit:

    1. Wow, I’m good looking.

    2. Trust me.

    3. I’m a totally honest person.

You may be the loveliest creature ever born, chock full of integrity, without a duplicitous bone in your body–but claiming you are any of these things will send up warning signals. Good people will shy away from you if you make those claims. If they’ve been working for you, fine and dandy–but I know I personally avoid those three “ship sinkers” with a passion.

I missed this movie when it came out in 1983.  Looks like  a dandy...!

I missed this movie when it came out in 1983. Looks like a dandy…!

    Good News Next

Obviously, not all prison pen pal ads by inmates fall into the same category. Admittedly, even a smattering of I’m gorgeous listings have the effect of poisoning the entire pool, but there are some genuinely attractive postings by prisoners seeking friends. Here are a few of those:

–I need someone who pops into my head knowing they will be interested in the good news I just received or the joke I just heard. I want to ask questions and get to know someone. I want to be reminded of what’s going on outside of here.

–To whoever would write me, I’m probably the most understanding woman you’ll ever meet. I must say, I have been through a lot, made many mistakes, and I have a past. However, it’s served to make me a better person.

–I am very open minded about new ideas in my relationship. I am incarcerated for resale.

“I am incarcerated for resale.” In that one, the woman is telling readers, “Hey, I bought drugs and resold them, got caught, and now here I am.” If you’re in for getting busted on a drug deal, it’s a positive thing to let any interested parties know about it up front. There are more people down for drug related offenses than all the rest of the prison population put together, but at least a potential correspondent doesn’t have to wonder if you’re a serial killer or a child rapist.

On the other hand, it’s sometimes a tricky thing, dealing with those who may not be familiar with the system. I’m no greenhorn, but when I first read that, I thought for a moment it was written by a female inmate who does not go around saying she has a sense of humor. Instead, she illustrates that sense of humor by listing herself as “incarcerated for resale”, a girl ready to go to the highest bidder upon release from prison.

It is so easy to be misunderstood.


Basically, the rules my wife and I follow when surfing the ads for a new prison pen pal are simple: Does the way she wrote her ad sound real, or is she simply blowing smoke? We’ve been fooled a few times, but you’ve got to start somewhere–and from your side of the bars, it’s a good idea to make your ad as sincere and authentic as possible. If you’re a scammer (you know who you are), it may not make much difference, but if you’re in it to win it, every turn of phrase is important.

Because, as Frank Herbert wrote in his science fiction classic, Dune, beginnings are such fragile things.



This cartoon isn't all that funny, but it does get the point across.

This cartoon isn’t all that funny, but it does get the point across.

8 thoughts on “Open Letter to Women in Prison Seeking Pen Pals

  1. I am absolutely terrible at writing letters. I mean, I do not write letters. I will call, or I will write a short note; but I cannot write a letter. Just isn’t in me. If you want a male inmate to write to, let me know. He is supposed to get out in January.

  2. Thanks, but our plate is pretty full at the moment. Besides which, we haven’t written a male inmate since wa-ay back in the day. In 2006, when I first ran a “prison pen pal” wanted ad under Males seeking Females in the Reno Gazette, half a dozen men (along with 14 women) responded, and I did correspond with two of those for a number of months–not the dude with the dead eyes, though. Then, in 1998, I think it was, an church friend of mine referred me to a hermaphrodite who’d had his vagina sewed shut right after he was delivered–THAT was a messed up fellow, right there. He was incarcerated in Sioux Falls, not nearly as crazy as he acted as a defense to keep others from messing with him, but insanely jealous. As soon as he found out we had other pen pals (three others at that time), he quit writing in what our mutual friend described as a huff.

    I got 41 years of writing weekly letters because of my mother. From the time I left home after high school (1961) until she passed on (2002), we wrote each other almost every single week. I didn’t much like the social duty, but after my father made a special effort to tell me during one of his rare visits to my home (with my first wife, in Spokane, circa 1971) that Mom worried herself sick when she didn’t hear from me, I stuck it out. It did make me quite relieved when she was no longer around to “expect” me to perform that duty, though. I was waiting to outlive my parents from the time I was 20. It took a long time.

    Plus, during my Army time, I wrote Vicky (my fiancĂ©e for most of the 2 year draft hitch, wife for the final 6 months) literally every single day I was gone except for those days I was heading home on leave or to get my discharge. She wasn’t quite as good at it but did write me an average of 3 a week, give or take. I never missed a day, though, whether on guard duty, KP, wiped out from a 20 mile hike with a fierce head cold, whatever.

    So I guess my “one Hub a day” routine, now one post a day, did have early roots, huh.

    Neither of my sisters is a letter writer, though, nor was Dad. Just me and Mom. Harriet and Donna did go to those once-a-year form letters for Christmas, which I rather detest, but to each his (or her) own.

    I found out just how totally some people “can’t write” when (maybe I mentioned this once) my friend Jerry, in Montana, was marveling over my prison pen pals (2004 or thereabouts). So I picked out three girls from the Internet (which he did not have), and he wrote them. Handwritten letters, but the results (or lack of results, depending on your viewpoint) indicated that perhaps I should have offered my editorial services as well. He was in his fifties, diabetic, still living with his parents, once engaged (she broke it off), never married. Two of the inmates never even bothered to reply, and the third one was a real disaster.

    I quit trying to play match maker after that.

  3. I had the weekly phone call to my mom. We have always seemed to have a really cheap long distance plan. Dennis and I both keep in touch with people over the phone. We only paid $10 a month for unlimited long distance for a long time. I called my sister, uncles and aunts too.

  4. Ah. That makes sense for your situation. In ours (Mom’s and mine), weekly phone calls wouldn’t have worked. For one thing, neither of us had a phone in the early years after my departure from home. For another, there were numerous times when working in a phone call would have been just way too much stress for me–either I was bogged down on a military base or running hard to make it to the next rodeo or running even harder, trying to sell livestock feed 108 hours per week, or….

    So, with her having become a stalwart correspondent from the time of her own childhood (to various friends and relatives), and me kind of “stuck” following her lead, there it was….

    As much as I resented the letter writing duty (which I did, but only sometimes), the phone calls would have been worse for me, with one exception. My youngest sister and I can talk with impressive comfort. The flow is just there, which I guess must have been there for you with your various relatives, too.

  5. What turns me off and sends me onto the next ad is:
    When they are trying to sell themselves, especially based on looks
    If they are looking for that right man/romance
    If they say that they are open minded
    If they post provocative pictures or share anything along the lines of them being provocative.
    If they are looking for donations or financial help in any way
    If they are looking for legal help
    if they talk about partying, drinking, doing drugs, as in they still want to live this lifestyle

    What catches my attention is:
    if they are just looking for a friend or penpal, esp if they don’t mention romance at all or share that they are not looking for romance
    if they know that they messed up and don’t act like they are the victim, and they don’t act like what they did was ok and that there was nothing wrong with what they did
    they show genuineness about learning from their mistakes, wanting to change/do things different

    I’m not looking for someone to post an ad about how they messed up and are turning their lives around and are so sorry for what they have done. But there is a difference between posting an ad about looking for a man, saying that you are looking for donations, you talk about partying and drinking with friends, and making all sorts of suggestive remarks, and posting an ad that sounds like you genuinely just want a friend through these hard times that can be a positive and support in your life.

  6. Tony, I agree wholeheartedly with all of your “red flags” except for two: I actually LIKE someone who says she (we only write to females) is open minded…and don’t mind a gal mentioning she’s looking for the right man. But that makes sense; our goals (my wife’s and mine) are not the same as yours when we write to inmates, and we prefer women who are bisexual or at least not offended by the concept.

  7. I enjoy writing and have coresponded with female inmates in the past. I was a drug dealer in the past so I’m street wise. I enjoy writing all types of woman from sociopaths to wall flowers. The main thing to understand is female inmates are cons until proven otherwise.
    The money game – No matter what woman is encountered money will become an issue. Inmates have basic needs and are allowed to buy items if they have money. Never offer money! You are their pen pal. Wait to see how she approaches you for money. If she is pulling strings with sad stories tell her you have a limited budget and are looking for a pen pal only. If she sticks around you got a keeper. Throw her a bone with a card and money credit to her prison account. She’ll be surprised and you’ll feel like a million bucks. This is the essence of have a female inmate friend. For me its a great way to bring hope, joy, and a little fun to someone living in a cage. Prison is not fun.
    The beauty game – These women are phoney but fun to write to. They are cons, self serving and selfish. I take advantage of their vanity and play with them. Women in general love humor. Beauty queens have open legs and fast money grabbings hands. They’ll get a kick out of teasing them about their looks but once the blood of money is not found they are gone.
    The lifers – These are the sociopaths. I enjoy their company because they are intelligent and dangerous. They enjoy playing maniplation games and are good at it.
    They are fabulous liers and I enjoy out lying them. Think if them as hungry lions in a cage. Don’t get close and never open your heart. These women are cold blooded killers. Understanding how they think and what made them is what I enjoy. Trying to get through the lies and finding a bit of truth is the fun part for me.
    The wall flowers – ALot of women are in prison because the men they were with commited crimes and made them accessiories. You can think of these women as innocent. There ads are simple and direct. They usually state that they are looking for a friend who they can share with and they will write back. Most women don’t get mail thats a fact. The wall flowers make good pen pals. I like more spice so I go for the nut jobs.
    My point here is inmates are antisocial to a large degree. They have lived hard lifes, hurt innocent people and been seperated from the general law abiding non violent masses. Inmates are people who have limited or no communication with the outside world. They love an honest letter from someone who is reaching out to them. Go slow and use your own good judgment. Once you think you are being played stop writing. You always have a choise because you’re not in prison. After a few inmates you will get a feel for the real deal. When that happens you’ve got a friend and will look forward to getting good ol snail mail. Good luck on a mystery adventure. I have enjoyec mine.

  8. Wow. Thomas, that’s quite a comment, and I thank you for posting it. That said–and since this article is an open letter to inmates, an exception to my other pages providing information to those of us on the outside who are interested in writing TO inmates–I’m adding the following:

    TO OUR INMATE READERS. Truthfully, there won’t be many of you, simply because inmates do not generally have direct access to the Internet. However, a few of you may have friends or relatives who send you a copy of the text of this page, or portions of it, so please note:

    It’s every bit as tough to find a “right person” on the outside as it is on the inside. So, to turn around what Thomas said and look at the other side, it’s wise to guard YOUR heart, every bit as much as it’s wise for the civilian writing to you to guard HIS heart…at least for a time. We’ve come across a number of inmates who trusted their correspondents with good reason, only to experience broken hearts in the end. Some have even “gone all the way”, hooked up with their pen pals when they got out, and found to their horror that they had jumped from the frying pan into the fire.

    I will say that Thomas (in my opinion) summed it up perfectly for ALL of us, either outside or behind bars, in a single sentence in his final paragraph: “Go slow and use your good judgment.” But that does not mean there’s no potential reward. My wife and I got scammed once by a woman we’d known (as a pen pal and over the phone) for nine years BEFORE she ever sent a single fib our way–and yet our latest pen pal (and probably our last one, due to my wife’s deteriorating health including dementia) is an absolute gem of a human being, having turned her life around the hard way in recent years.

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