What To Put Into a First Letter to a Prison Pen Pal


As Well As What NOT To Put In

The need for a letter writing guide for communicating with prison pen pals became clear to me in 2004. At that time, my wife and I lived in Anaconda, Montana. More days than not, my “me time” was spent having lunch with a close friend at MacDonald’s. Let’s call him “Jack” (not his real name).

Jack was in his early fifties, a truly good man, but had never been married. He had been engaged once. As we visited regularly over double cheeseburgers and dollar fries, the conversation sometimes touched on my ongoing practice of writing women in prison. Then, natually, came the question:

Could I share a few?

What I did was to pick out a few ladies I thought MIGHT be compatible with him, and encouraged HIM to write them. (He does not have a computer.) The results were disastrous, and I suddenly realized that not all people knew how to do this. So let’s get started.

Thankfully, we have word processors these days.

My laptop with a sample prison pen pal letter begun.

My laptop with a sample prison pen pal letter begun.

Things To Include

Prisons have strict rules about permitted correspondence. Each state is different, but a few things tend to be pretty universal:

1. Place your full name and address at the top of the letter every time you write (not just the first time). The mail room usually opens the mail, trashes the envelope, and gives the inmate ONLY the contents. Without that full address, the institution will not trust you and your friend won’t know where to write.

2. As your opening statement, BRIDGE. That is, give your new friend (male or female doesn’t matter) a reason to see common ground between you. It could be something as complicated as a taste in poetry or as simple as the fact that you hail from the same state. Remember, you are a stranger, and the recipient’s life has not likely given him or her reason to trust people at first contact.

3. Tell a few things about yourself, honestly and openly. Age, background, physical description, interests, education, whatever. Not ten pages of biography; there will be time enough for that. But a page or so to provide the beginnings of an accurate picture of you as a person, yes. Something funny is okay (within reason), and if you have trouble writing humor, I’ll even help (if you want) for free.

4. Without being pushy, say something about what you are looking for. Just a platonic friend, or getting to know each other, or (as we have done for specific situations) a frank statement. (Such as our advising our goal to eventually have additional staff to care for my disabled wife in return for room and board.)


Things That Should NOT Be Included

1. Any specific mention of a prison pen pal ad. In most states, that does not matter, but some officially hate pen pal ads and will confiscate any letter they know came from one. Contraband, they say. Which is ridiculous, but there it is, with Florida being the absolute worst. Most importantly, such a mention can actually get the inmate in trouble for daring to place the ad in the first place!

2. Do not make mention of his/her crime in your first letter. If you get a return letter, there will be plenty of time to discuss that later.

3. Do not include anything OTHER than the letter itself. Every state has a website where we can THEORETICALLY check out the rules for corresponding with inmates, but not every site is easy to access or navigate. Simplest is to wait, even on photos or stamps, until your correspondent can advise you regarding the rules at that institution.

In closing: Pam and I have been corresponding with incarcerated folks for more than seventeen years and expect to continue as long as we live. To us, the rewards are more than worth what effort it takes. Hopefully, you will agree.

Slammer! (A New Women-In-Prison Musical)

79 thoughts on “What To Put Into a First Letter to a Prison Pen Pal

  1. Wow. That’s a really good question–but I’m not 100% sure I know the answer. It’s never come up before.

    I’m guessing you’re an artist and would like to include an example of your work. Unfortunately, I don’t know if it might be a problem or not. My best guess (but it’s just that, educated somewhat but still a guess) is that you’d have no problem with a drawing if you did the drawing on the same sheet of paper containing part of a letter’s text–which would make it obvious to prison staff that it was part and parcel of the letter per se–but that a drawing on a separate sheet might be a problem, depending on the state.

    Each state has its own rules regarding photos. Most of them are automatically suspicious of anything (photo) printed on plain paper; they seem to worry about it having been copied from the Internet. If it were me, I’d err on the side of caution and NOT include any drawing done on a SEPARATE sheet of paper. Inmates sending out drawings have no problems at all, but incoming stuff is looked at a lot more closely.

  2. The problem with pictures being printed on a printer is that the inmates will extract the ink to use in tattoos. That is what I was told. Those inks can be extracted, surprise to me too. If it is done with pencil, it is usually allowed

  3. And people in juvenile detention can receive letters from “strangers” too? Thank you!

  4. Carolina, if you don’t have the ID number, the letter will probably never be delivered to the inmate. Fortunately, the DOC (Department of Corrections) website for most states (though not all) will allow you to plug in the name of the inmate you’re trying to find OR the number…and once the profile pops up, bingo, you’ve got the information you need.

    I know nothing about the rules for juvenile detention–but would be very surprised if mail for juvie detainees wasn’t monitored even more closely than for adult inmates in prisons. Plus, I would think an adult “stranger” attempting to write a juvenile might want to consider the possibility of being branded a pervert for even trying. It’s a tricky world out there, and CYA (Cover Your A**) is all too often the first rule of survival.

  5. Wow, that’s so sad. I just wanted to send a support letter, I’m an adolescent, so, they cannot think that. There’s no possibilities without the id number even if it’s a famous case? Or it’s even harder? I think there’s no way to find the number. I think i will give up. Thanks for the reply.

  6. Carolina, I did not know you were still in your teens. If you’re 17 or under, then obviously no one is going to try to stick the pervert label on you for sending a letter to a juvenile in detention; you’re 100% right about that. In detention, there won’t be a Department of Corrections number; that doesn’t happen until a person is convicted of a felony and assigned prison time in either a state or federal facility.

    I don’t honestly know if a famous case makes it harder or easier. I do know a lot of high profile cases have attracted mail that does get through, but it’s not something I’ve ever looked into. If the person has gone on to prison, though, there should be a way to find the ID number; it’s essentially a public record. Some states make it harder to find than others, but in most cases, there IS a way. One thing you might try for a famous case is simply to Google as follows: [person’s name mailing address]. Out of curiosity, I just tried that for [Jodi Arias mailing address]–Jodi being a high profile convicted felon here in Arizona–and immediately came up with her full mailing address, including ID number, on a Facebook page hosted by “…the Voice for Jodi Arias.”

  7. I searched for her number in a couple pages, and there is no information, i thought it was because she is a minor. I think there is no ID number because she’s still on trial, right? So I can send the letter without the number? Sorry about all the questions, i’ve never contacted someone in jail, but I’m really worried about this case, and I really want to send support.

  8. Sorry about the mistake and the bunch of questions, I finally understood, she is detained. I was a little confused. Detainees can receive letters from strangers? That is my last question. She’s still on trial, so she’s not a prisoner.

  9. Carolina, it sounds like you’ve got it figured out. πŸ™‚

    I’m pretty sure she should be able to receive “mail from strangers”; there are news articles all the time that talk about mail received by high profile defendants being held in jail pending the outcomes of their trials. Rules do vary from jurisdiction to jurisdiction, though. For example, prisoners (not detainees) in Florida really have a tough row to hoe when they place prison pen pal ads–because the state of Florida purely hates that whole idea and the facility (state prison) will reject any incoming letter that looks to the readers (prison personnel) like it’s coming from a stranger. So in Florida (at the state prison level, anyway), I’ve always been careful how I worded my first letter so as not to trigger any “gestapo alarms”. I don’t know if that oppressive approach applies to county jails in Florida; it may be strictly a state DOC (Department of Corrections) attitude.

  10. I sent my letter, from my country (Argentina) to USA, Wisconsin. If I understood it right, people awaiting for trial (people in jail) doesn’t have an ID number, but when you need to send letters to people in prison, then, you need a number. I thought it was all the same. In my country everything is different. that’s why I was so confused. She’s in county jail. Sorry for coming here again, but I sent the letter 18 days ago. And I didn’t get a reply, maybe she didn’t receive it, or maybe she can’t send letters to other countries? Or I didn’t do it right and I needed her ID number? I’m feeling annoying, but nobody is so generous to reply all this questions and I need your help. I think i’ll try to send another letter. And I need to get all the help I can, so I can make sure she receives my letter.

  11. Carolina, there are several possibilities:

    1. Eighteen days seems like a long time, but I’ve seen prison mail take even longer than that to make the round trip–and that’s just in the United States, between states.

    2. If she’s a celebrity case (which I seem to recall you mentioning), she might have an awful lot of mail to read and answer.

    3. If I recall correctly, international postage is more expensive than domestic postage. She might not have the funds to pay for the stamp. I don’t believe she would be prohibited from writing to you in Argentina.

    Overall, I’m guessing you did everything right–but if she’s receiving a lot of mail, she might or might not ever get around to answering your letter. I never send a second letter unless a new pen pal has answered back at least once–but it might work for you. If she chooses not to reply, though, I don’t know of any way to be 100% certain she received your letter. Sometimes, we’re simply left not knowing.

  12. Thank you so much, I think all I can do is waiting. If I don’t get an answer for too long, maybe I’ll send another letter. But you said it takes more than eighteen days sometimes, and i’m in another country, maybe that’s the reason. I’ve read that receiving letters from Argentina to USA can take about 5 to 12 days. So i’ll be patient. Thank you again.

  13. Patience is good. No fun, of course, but still good.

    We had one letter mailed to us from a pen pal friend in Arkansas this past January…that managed to get lost in the mail system somewhere for nearly a month. It did show up eventually. Anyway, as always, you’re welcome.

  14. Wow, Florida prisons have a tendency to toss mail from strangers to inmates? I’ve never encountered that that I know of. I seem to have heard back anyone I wrote to in Florida.
    Carolina, there is also the fact that not every inmate is going to want to write back. I’ve had a number of inmates not write me back that I wrote to. Not sure how many didn’t get the letter, and how many just weren’t interested.

  15. Tony, the big red flag that I’ve come across in Florida is if you mention up front in your letter that you found the inmate’s profile on a prison pen pal site. If you’ve done that and still gotten replies back okay, I’d have to say you’re living a charmed life.

    If the rules have changed recently, I’d like to know. In the meantime, the Huffington Post did an excellent article in 2009 on the topic titled Prisons Ban Inmates From Having Pen Pal Ads. Here’s the link:

  16. Well, it has been awhile since I’ve began writing an inmate in Florida that I found from the ads. Maybe I didn’t mention that I found them in the ads. It’s been so long, that I don’t remember.

  17. Curiously enough, I never did write any inmate in Florida–just read up on what others were saying, the warnings and blockages and such. We had a long (years) correspondence with one Florida lady, but she’d been busted in Georgia and was incarcerated there instead of in her home state.

  18. I can’t get rid of this feeling for weeks that I need to contact this inmate in Lakin Correctional Center because now after learning her entire case she’s totally got my interest and sympathy. I won’t say names because nobody would understand but it doesn’t matter anyways..So can I actually make mention of her crime in my letters? I don’t want to get her in trouble but this case came to a close already and in 2014 she was sentenced to life anyways. I do have a few things to tell her. Can I possibly mention names in my letter like the name of the victim or the fellow offender? I heard it can make them suspicious about me. Is that true? I’m a little bit worried knowing all letters sent to inmates opened and read by the administration before being delivered. I’m so helpless I’ve never done this before..
    Thank you for your help in advance.

  19. Connie, I would definitely NOT say anything about the crime, victim, or the fellow offender–not one word–in your first letter. You don’t need to feel helpless, though. Yes, incoming inmate mail is opened and at least scanned by staff before being delivered to the inmate–which, curiously enough, is not usually the case with outgoing mail. That is, they’ll (most of the time) ignore whatever the inmate has to say but are very wary about incoming correspondence.

    Which makes some sense when you think about it. If you were the one running the prison, you certainly wouldn’t want a letter coming in that said something like, “Hey, here are the details for your prison break next week; be ready!”

    First letters can indeed be tricky to write. You want to get past the censors in the mail room, don’t want to say anything that might get the inmate in trouble, don’t want to get the prison looking at you strangely, and do want the inmate (who of course does not yet know you from Adam’s off ox) to be intrigued enough to write back. So, how do you deal with that?

    From our experience, while the basic “risk points” are pretty standard, every situation is also unique. Just at a guess (from what you’ve stated in your comment), you might want to say something like,

    “Beautiful day here. Got me to thinking about a few things we seem to have in common….” And then you list a few nonthreatening specifics, always looking for a way to bridge. Over the years, Pam and I’ve done that with dozens if not hundreds of different things–birthdays in the same month or astrological sign, work backgrounds, being homeless (which Pam was at one time) or a writer (which I am), etc., etc., etc.

    Bottom line, you want to convey sincerity, but nothing too heavy. Beginnings are such fragile things, and the heavy stuff can always come later. You can’t guarantee the inmate will respond, but you can at least write carefully enough to be pretty sure the inmate received the letter.

    Hope this helps a little.

  20. Well, thank you so much it all makes sense now. At least now I know I won’t make mention about the crime itself. I just thought it wouldn’t matter since her case has been closed and she pleaded guilty. I guess it’s always hard when you’re kinda “siding” with the public enemy even more when it’s an actual killer. I better be aware what I say, right? Well, I’m not saying I’m ok with killing people, period. But I do know what it feels like being a psychopath and it’s a common trait that they get bored easily, which contributes to risk-seeking behavior. For me it’s always been self-harm tendencies, no big deal just making you feel alive, or simply feel something. When your emotional life is too shallow to feel anything it’s like you know certain things are wrong but do not feel the norms. People don’t understand how she can’t feel guilt, empathy or remorse and that she didn’t even say she was sorry ever. So while the fellow offender cracked & confessed then also apologized- hence she got far less time- but in my opinion none of this is meant to imply that she is somehow less guilty. She committed the exact same crime as the other girl did. Basically that’s what I wanted to write in my letter and that’s when I only wanted to make mention about the fellow offender. That’s it. Also I wanted to tell “the inmate” that I know what it’s like when nobody believes you anymore and I was gonna ask her if there’s anyone she can talk with. I’m sure she realizes the things she did are completely wrong but maybe not because she feels remorse but because of she ended up wasting her own life in jail. So I’m sure she knows it was not worth it and she would never do anything like that again. I just hope she can get outta prison someday. Next parole hearing date is 2028 though. You know I feel bad for her because everyone’s gonna remember and hate her for good. To be honest I don’t think they’d let her out after serving this 15 years but that’s what I definitely wouldn’t tell her in my letter. it’s the last thing she needs right now. However I found out haters are now being encouraged by some friggin site to send letters filled with hatred to this girl in prison. How disgusting though! If she’s really getting these letters she def won’t even open mine. Why would she? She doesn’t even know my name anyways..

    I totally agree, “beginnings are such fragile things, and the heavy stuff can always come later”. πŸ™‚ I don’t mean to tell her anything too heavy I just wish it wasn’t so hard to make the first step…

    Okay thank you again for taking the time to read this. πŸ™‚

  21. Connie, I do understand where you’re coming from. So called risk taking behavior is no stranger to me (nor to my wife for that matter), though hopefully we’ve outgrown most of that by now. (Earlier in life, Pam did things like sing on stage with Janis Joplin at Woodstock, hook up with the Hell’s Angels for a while in an attempt to get her sister clear of a bad situation, drag race VW bugs with V-8 engines, etc. I competed a number of years on the professional rodeo circuit, riding bulls and saddle broncs.)

    That said, if the inmate does receive your letter from the mail room, she may or may not read the entire thing–but she will most likely at least look at the opening paragraph to see if it piques her interest.

  22. Wow you guys rock!! πŸ™‚ Seems like both you and your wife chose the adventurous path. I respect those who have been through a lot in life. Only they have enough experience to say things. I’ve always preferred to listen to them and take their advices instead of theirs only with booksmarts…
    I think sometimes you gotta take risks, and as a result, sometimes you end up in serious trouble but all of this is much better than wasting your life living it according to social expectations.

    By the way I never finished my letter to the inmate. I always thought writing was my thing but considering now I’m completely stuck on this short letter for days I must have been wrong. I’m so lame! πŸ™‚

    Although I only came here for some help with my letter I’m really glad we had all this talk. I don’t want to mess up your comment section though so if you don’t mind we can continue via email.

    Have a nice day!

  23. Sure, Connie; feel free to go the email route if you prefer. Don’t know if you’re “lame” or not–I write all the time and have been hung up on a letter more than once–but ny email address is always listed on the Contact page (see Index section at the top of any page). You have a nice day, too. πŸ™‚

  24. Ava, let me answer that in two parts:

    1. Yes, you can do that. It’s usually not necessary to put the address on the back; my normal procedure is to write the following on the back (and no more): “Property of Joe Inmate, #xxxxxx”. That way, everybody knows to whom the photo belongs, and they’ve nearly always reached the inmate. (Although there can be thieves working in the mail room, or incompetent personnel, and the photo might possibly go missing. Until you hear back from your correspondent, you never know for sure.)

    2. I generally don’t send a photo until the second letter, simply telling the inmate I’ll gladly send one after receiving a reply. However, your situation is different. Pam and I amount to an older couple (I’m in my 70’s now, she’s in her mid-60’s) writing to younger inmates (the “youngest ever” was 25 with a 20 year sentence, the oldest in her late 30’s). But if you’re a female writing to a male inmate, it’d be surprising if you didn’t get a reply, so sending a photo with the first letter might work out okay for you.

  25. Hi, I want to write to inmates since a long time but don’t know how since is the first time I do this. I have so many questions, I hope I’m not being too annoying.
    First of all, what type of envelopes can I use? I’ve read that some prisons don’t allow tape or envelopes that are this ones that comes with the glue already and you just put some water and seal it.
    The paper can be any kind of paper? The ink has to be blue or black?
    Some of them have limited money and they can’t afford stamps (specially overseas), in the letter can I send them extra paper, envelopes and stamps?
    If I want to send photos do I have to send them in other envelope, separated of the letter or can it be together?
    I’ve read (again) that some prisons don’t allow that either.
    Now I have questions on what to put in the first letter. I don’t want to make him/her uncomfortable talking about things he/she can’t do because of his/her situation.
    I think that’s all.
    Thank you for your help in advance.

  26. ↑↑↑↑↑↑↑↑↑↑↑↑↑
    Some of them have limited money and they can’t afford stamps (specially overseas), in the letter can I send them extra paper, envelopes and stamps?
    I’ve read (again) that some prisons don’t allow that either.
    If I want to send photos do I have to send them in other envelope, separated of the letter or can it be together?*********


  27. Victoria, first of all, no matter how many questions you need answered, you will NOT be annoying. πŸ˜€

    Now, a few answers:

    1. Yes, some prisons are touchy about tape, so I avoid that as much as possible “just in case”. But I’ve not run into any facility that had anything against the self-seal envelopes. In fact, those are the only ones we use! I stick to regular business sized white envelopes. Just checked our current box of envelopes, and the size is 4 1/8″ x 9 1/2″. It could be there’s a state where self-seal envelopes are a problem (just peel off the paper tape and close the flap), but it’s nothing we’ve encountered to date in Arizona, Arkansas, Georgia, South Dakota, Montana, Nevada, or California.

    2. Do NOT send extra paper, envelopes, and/or stamps. They will be considered contraband and might even get the inmate in trouble. You’ll need to establish some sort of rapport with your correspondent FIRST in order to find out from them what forms of “postal support” might be acceptable.

    3. Pictures are a special case unto themselves. States vary. The inmate will know whether his/her facility wants photos included in the same envelope with the letter–usually yes, but it’s not safe to assume ANYTHING. Also, there are definite restrictions on picture SIZE (usually 4″ x 6″ maximum, but check first anyway) and on the NUMBER of photos that can be sent at any one time. And I always jot down the following at the bottom edge of the back of each photo: “Property of John Inmate, #xxxxxxx”. We’ve seen a few photos go completely missing, never delivered to our friends, but putting that “property notice” on the back does seem to reduce the frequency of what we strongly suspect is theft in the mailroom.

    4. As far as we know, the paper can be “any kind”–I type ours, but I’ve known folks who wrote inmates on whatever lined notebook paper they had handy–and either blue or black ink should be fine.

    5. What to put in the first letter. Well now, that’s the big one, isn’t it? But that’s also what this entire post has been all about from the beginning, so hopefully the answers are there (in the text of the post).

    Best of fortune with your writing endeavor, and believe me, you do NOT need to be sorry! πŸ˜€

  28. Thank you again for answering all my questions! It’s really hard to find someone that answers all your doubts with this subject.
    All though, here in my country, the self sealing envelopes are nowhere to be found, maybe I can look up in Amazon but are this ones that I mentioned capable of use? The ones that come with some glue in the lapel and just need to add some water.
    The photos can be printed?
    Is there subjects that are better to avoid? For example, family.
    Thank you again! Have a good night. Xo

  29. I don’t believe the “add water” envelopes are in use in the U.S., so I simply have no experience with those. The only ones I’ve ever used are either (a) lick them and then seal or (b) self seal. So I honestly cannot answer that question for you.

    As for the photos, they can certainly be printed–but some prisons won’t accept them if they’re printed on plain paper, so it’s much better to invest (if you can) in a pack of regular photo paper for your printer. Using that, the photos are going to be seen as regular commercial photos and will always pass through, at least so far as I know.

    There are many subjects to avoid: Firearms, drugs, crime, sex (at least at first, though it’s generally okay to get into some of that at some point IF you feel it’s appropriate), and yes, you might not want to bring up family right away. Kind of ease into it later…unless there’s a potent bridge you think might work well. Example: We wrote one pen pal (some years ago) who mentioned in her pen pal ad that she’d lost a sister to suicide…and when I wrote, I included the fact that Pam, too, had lost a sister that way. Didn’t overdo it, just dropped it in there. But generally, your intuition is right on; save family for later.

    Thanks for the Xo. πŸ˜€

  30. Hi there again!
    The lick and then seal envelopes are what I’m talking about! I don’t lick them because I don’t like that so I just add water. I’m guessing they are allowed.
    I forgot to ask, the envelopes must have a particular size?

    Thanks again. Take care! πŸ™‚

  31. Oh! Sure, those envelopes will work just fine. I should have realized. Used a sponge and water bowl to seal thousands of that type some years back, when I had a sales business and was putting out a sizeable newsletter every month.

    Size shouldn’t be a problem. We’ve sent missives in everything from the small fold-’em-tight envelopes to business size to the oversized types with greeting cards in them. Never had one bounce because of size.

  32. Thank you!!!!!!!
    One more thing, if I want to sent them books do I have to buy them on Amazon and in the shipping address put their address, right?
    Because I’ve read that you can’t ship books from your main address.
    Have a nice day!! πŸ˜‰

  33. That’s exactly right, Victoria. Books have to be sent from a bookstore, not from a residential address, probably because the prisons don’t figure a bookstore is going to try to smuggle contraband in by using a book, whereas a personal friend might do just that. We use Amazon only, precisely as you described.

    May the blessings be.

  34. On return address, I was thinking of just using my first name and p.o. box? Will that pass the test with the people who review letters.
    I did not feel comfortable putting my last name.

  35. Sue, if you’re not comfortable including your last name, you’re better off not writing at all…because no, first name only will NOT pass the test with the people who review letters. They won’t even deliver the letter to the inmate.

    That said, the P.O. Box is definitely a good thing to use. We’ve done it both ways over the years, sometimes using our actual street address, but a couple of years ago we were more than thankful to be using the P.O. Box address (which we’ve done since we moved to Arizona in 2009). One lady we’d been writing got out to a halfway house, we figured out she was diving right back into the world of street drugs, and we severed the relationship–in a messy sort of way for a while. Lots of cursing and screeching over the phone when she realized her Golden Goose had suddenly gotten cooked. Had to block her phone number. Weeks later, she got busted again and went right back behind bars.

  36. oh wow. Thanks for letting me know. I wonder why that is (?) Especially if the content in the letter is nothing but love and encouragement? Hmmm….
    Thank you for letting me know.

  37. Sue, I can tell you why that is: Because a whole lot of inmates are connected with people on the outside who deserve to be on the inside. It’s nothing personal against you or me; the prison staff simply can’t afford to trust anybody who looks “iffy” at all, like they might be hiding their last names because they might, you know, have something to hide. For example, they don’t want inmates having outside connections who help them smuggle contraband into the prison, run criminal enterprises outside the prison, etc.

    Which is a wee bit silly in one way. Any of the truly shifty characters writing inmates could (and some probably do) simply use assumed names, since it’s not standard practice for prisons to do background checks on routine correspondents. They do run checks on anyone who wants to get on an inmate’s visiting list or even telephone list, though.

  38. Ghost32, I started writing a prisoner from OR just over a year and a half now and we would write each other every day without fail. Then in one of his letters about 3 months ago he stated he needed $200 he didn’t ask for money he just mentioned he was saving to get $200,so I wanted to surprise him I sent him $200 after this I was lucky to receive a letter once a week or a 2 minute phone call every other week. After corresponding for maybe 8 months I asked him what the charges were because he said he would never lie and he was faithful, well I recently found out he lied about his charges and where he was from, now he wont write me because I asked him WHY he lied? Is this a general practice with inmates they just try and get what they want and can until there release date, Because that just broke my heart because I thought he was really falling in love as I did. Now I’m so broken I don’t want to Love anyone else. p.s I didn’t start writing an inmate to fall in love I started because a friend told me that we might help someone fill their long days. And I just fell in love. As I said he didn’t ask me for any money or food or cloths he would just ask me to be as him “LOYAL, FAITHFUL, & HONEST” but turns out he never was. Should I put the breaks on this whole writing thing or should I not blame every inmate for one bad one? If the latter how can I be sure they aren’t out to break my heart too or again?? Thanks

  39. Hi, my name is Jeremy. I am interested in a female inmate. I want to send her letters. Online I got different information that it is not good to mention the website (in this case meet-an-inmate.com. Unfortunately in my first letter I mentioned this website to introduce myself. Do you think she will never receive my letter? She is in Albion Correctional Facility (New York). Do you know are they very strict? I am based in Germany and I do not know the rules. Do they read the whole letter? Must I thin about every single word? Maybe you can help me.

  40. Additional I have the following questions:

    1. Can I send a small photo (size: passport photo)?
    2. Can inmates use internet/emails? Is it different state by state? Or is it general not possible?
    3.Which special rules I must know for Albion (New York)? It is a prison (medium level). Is in such prisons more possible and they are not so strict?
    4. I do not know the law system in the USA. She received a sentence 5-15 years. Is the meaning that she can appeal for grace (probation) after 5 years? Or is there a chance to commute the sentence earlier? Otherwise is it possible to reduce the sentence after 5 years for good behavior?

  41. Sorry that I bother you again. I send my letter with a photo. The letter was typed on the computer and I put two photos on this letter ( 2 photos of myself). Do you think she will never receive this letter? Do you think it is better to send the same letter again without photo? Is it possible to put graphics in the letter? Or do you recommend simple letter?

  42. Ray in Cali: I’m VERY sorry that for whatever reason my website did NOT notify me that I had a comment from you on this page, hence the delay in responding. But here’s hoping you check back at some point and find this. Let me answer respond “by the numbers” as follows:

    1. I can’t tell you what you should or should not do–put the brakes on, keep on looking for a truthful inmate, are anything in between. Only you can make that decision.

    2. That said, I CAN tell you a bit about the odds when it comes to writing inmates, based on more than 20 years of personally writing to more than 200 inmates.

    3. The majority of inmates will not be open and honest up front. There are multiple interlocking reasons for this, a few of which are: Something like two thirds of all inmates have charges that are in some way drug related, and they can’t have lived in that environment without learning to lie like a rug…many have suffered abuse or molestation early in life, and/or are mentally ill, which colors their outlook on life…they are surrounded by a culture (prison culture) which tends to encourage them to rip off everybody they can and think it’s a good thing…and even when they’re determined to get straight, to clean up their acts, the task before them is enormous.

    4. That said, my wife and I do not regret having written to so many over the years (not all at once, of course; some would drop out or get cut off by us and others would take their places). In 2011, a female inmate who had honestly planned to come live with us when she got out, helping me take care of my wife, had to pull the plug–but with good reason, as her adult children (who had shunned her up to that point) reentered her life and brought her back into the fold. Despite our rather broken hearts (especially my wife’s), we did that lady a lot of good and helped her get a real start when she left prison.

    Then there was another girl who started out honest but, after corresponding with us for more than ten years, she scammed us pretty thoroughly. The Warden at her institution spotted the problem, alerted us, and if we had pursued recovery of the money she’d taken from us under false pretenses and was building up in her prison trust account as a nest egg, she would have faced new charges. We did cut her out of our lives, but she was keenly aware that (a) she had cost herself badly and yet (b) us letting her off the hook gave her a chance. She made the best of it and, so far as we know, has been doing okay “back out in the world” after a 20 year sentence for murder. Again, in the end what we did helped her, and that was a good thing, though the betrayal did sting, you betcha.

    And then we tried one more time…and hit paydirt. Our “last prison correspondent ever” has become very close to both of us. She’s pulled herself up from a life of tough environment and wrong thinking (over the past several years), will be due for parole shortly, and once that’s done, will indeed be joining us. The trust level between all three of us (my wife, our inmate friend, and me) is sky high, and all of that twenty-plus year experience is finally paying off in relationship terms.

    Bottom line, we’ve also seen other people succeed with relationships with inmates. It CAN be done. The only question is, “Am I willing to pay the price?” (Not knowing for sure what that price might be.)

    It did take us a while to learn not to send “surprise money,” ever, and to consider monetary requests from inmates very carefully before committing.

    Hope this helps.


    Jeremy Cooper: First of all, comments and questions never bother me. Feel free to ask as many questions as you like.

    As I did in response to Ray’s query, by the numbers:

    1. Simple letter only, especially for the first one. Or, if you think maybe she didn’t get the first one, for the follow up letter.

    2. I’m not familiar with prison mail rules for New York. Every state is different. In Arkansas, for example, they’re just now instituting a mail policy change that is really ugly. NO mail reaches ANY inmate directly after August 21, 2017 (unless the policy gets reversed, which it may). Instead, the mail room PHOTOCOPIES the mail and gives the inmate the photocopy only. Also, they’ll trash anything longer than 3 pages. (

    We have a friend currently incarcerated in Arkansas, and thank goodness we have email privileges set up with her as snail mail is now pretty much out of the question.)

    3. No photos the first time around. The inmate will need to let you know what the rules are for her institution. Even for much more liberal states than Arkansas, there are usually rules on how many photos can be sent at one time, size restrictions, etc.

    4. Currently, most of the states with which I am familiar do have email setups available. I’m not sure all do, but there are a few companies out there providing these services. Once you’re in contact with her, the inmate can tell you how to go about that if it is doable. All we have to do is pay for “postage,” so may “credits” per email, with a size restriction on each email. Both text and photos can be sent that way, once the account is set up properly.

    5. Internet, no. Inmates are not generally allowed any Internet access.

    6. There is pretty good rundown on Albion mail rules at this link:

    Based on that official page, the odds are pretty good that she WILL receive the letter, but you never know. We’ve had mail disappear every once in a while…though thankfully not often.

    7. I wouldn’t send exactly the same letter again, but rather a second letter explaining that you’re not sure the first letter was received. You can cover the same information on yourself, just reword it a bit. But don’t rush doing this; mail turnaround times can be slow and it might cross in the mail with her reply. Patience is critical.

    8. I know almost nothing about specific quirks in New York state law, but generally, most sentences allow the inmate to try for parole (NOT probation, which is a term applied to someone who never went to prison at all, just had to do the supervised probation.)…parole first becomes available (in most cases) at the halfway mark of the sentence. However it is rare (in my experience, anyway) for the inmate to be granted parole the first time around. Although New York may be different. I would suggest Googling “parole rules New York” or some such to research this issue.

    9. Do they read the whole letter? Good question. The short answer is that one must assume they do. Every word you write must be considered in that light. I don’t even mention anything about, for example, my disabled wife’s prescription medications in a letter or email–because a prison mail room reader might see that as “code for drug stuff” or some such. Assume Big Brother is looking over your shoulder, breathing down your neck, always.

    In practice, there’s no way they read every word of every communication. Many mail room workers are bored, overworked, lazy, incompetent, untrustworthy, petty, vengeful, or any combination of the above. Think about it. If you were setting your sights on a stellar career, how likely would you be to think, “Hey, I know! I want to sort mail for prisoners for the rest of my life!” You get what you pay for. So common sense tells us a lot gets missed.

    But you can never assume YOUR letter will be skimmed over lightly. Always prepare for the worst and you’ll never be disappointed, right?

  43. What do you think about the question regarding meet-an-inmate.com. Can I mention this website in my first letter to start a conversation?

  44. You’re welcome, Jeremy.

    I’ve never written to anyone in Texas, so can’t help you there. Or rather, if memory serves, we did write to one girl in that state some years back, but she did not reply.

    I try never to mention meet-an-inmate.com or any other prison pen pal website, regardless of the state involved. Florida definitely has the worst reputation when it comes to that, but I simply figure better safe than sorry. However, I have on occasion referred to something the inmate listed in her ad…but without pointing directly at the site. For example, let’s say her ad stated that she loved rodeo (that did happen once with a pen pal in Nevada). My first letter mentioned, “Your love of rodeo inspired me to write. While not active in the sport now, I did compete professionally in saddle bronc and bull riding back in the day….”

    She was sharp enough to realize I’d read the ad and did write back. As it happened, I met my wife (not an inmate) right about that time, or she (inmate) and I might have hooked up.

  45. Unfortunately I always start a letter with the source where I found it ( in my profession I have to send always a lot of letters). I did not know that this could be a problem. or is it ONLY in Florida a problem?

  46. You mentioned that you had contact with about 200 prisoners. What was the percentage of inmates. What was the percentage of prisoners who did not answer you? This woman in Albion is very important for me and I do not want to make mistakes.

  47. Only a handful did not reply at least once, but a friend of mine wrote four inmates one summer and only heard back from one of them, the difference being that I write well and he, quite frankly, does not.

    Your English is far better than my Deutsch, believe me. During my U.S. Army time, stationed at the Fliegerhorst Kaserne not far from Hanau (1964-65), I doubt I learned more than fifty words. Just enough to ask a fraulein to dance or to order weinerschnitzel, that was about it.

    The greatest danger in mentioning a prison pen pal site in your letter is not so much that she won’t get the letter–although in Florida that may be true. Worse is the fact that if it’s a state that frowns on such sites, receiving a letter that mentions something verboten may result in the inmate receiving a DR, or Disciplinary Report, thus being punished for having placed an ad in the first place even though she did not write the letter. When I first started writing prisoners in 2006, I quickly learned to become extremely protective of the girls with whom I was corresponding. I don’t know how many states actually penalize inmates for prison pen pal ads. As a best case scenario, Florida might be the only one.

    Or not. I just Googled the topic and came up with this excellent link:


  48. Thank you Ghost32. I know Hanau as well because I am from Frankfurt. I think in New York it is easier than in other states like Oklahoma or Florida (I hope). The experience I have now will help me in the future.

    And be honest for me Jennifer is not a criminal. 15 years imprisonment for a car accident (only with broken bones, without dead people) is a very hard sentence. In Germany killer and murderer get less sentences. In general I prefer a strict law system but in this case 15 years are too hard and I can understand that she has a problem with this sentence. The aim of my letter is to support her and not to punish her. I know it is not good to mention strong feelings for her in a letter (maybe later) but I have this feelings.

    What will happen when i put an email address in a letter. Nothing? Or punishment for her as well? My friends are worried that it is dangerous to write this letters to inmates. What do you think? I know only the case of Lee Grace Dougherty (you can google the details) where a gang tried to blackmail the penpals. Even on such websites like “meet an inmate” or other websites there is a information about this. What is your experience? I cannot believe that Jennifer is such a person. I saw her interview on youtube and in my research I read a lot of articles about her. What do you recommend to do or not to do?

  49. I know it is not allowed to talk about the case/crime of the inmate. What can I do when I am interested in more details about her appeal or other facts? Is itfor her possible to write about this topic?

  50. Is there a regulation about the amount of pages of a letter. Is it possible to send a letter with 10 or 12 pages?

  51. Jeremy, I wouldn’t send an early letter with that many pages. If Jennifer is honest as you believe, it might overwhelm her, give her a fear of, “Wow, this guy is over the top.” And if by some chance another less ethical inmate spots a huge letter like that, the first thought will be, “Okay, sucker on the line right here!” It is never safe to assume that your letter will not find its way to people you’d rather didn’t see it. We’ve had pen pals who simply went to take a shower, forgot to lock their foot locker, came back, and had been robbed of everything. Also, there have been instances when an inmate was transferred to another prison and not all of her stuff made it to the new location. Thirdly, people have come out of being “in the hole” (solitary confinement for some violation of the rules, real or imagined) and their stuff was gone.

    So ALWAYS be aware of those possibilities. NEVER put the kind of personal information in ANY letter that could hurt you if it was posted publicly for the whole world to see.

    I agree that the danger for you, writing from Europe, should be very low. In this country, most of the time we use a Post Office Box rather than our street address, just for that little bit of security knowing that the P.O. Box will not point directly to our home, but there have been places and times (we’ve moved around some over the past 21 years) where we did use the street address. The closest thing to “threatening” was a few years ago when a girl who had been released from prison to a halfway house, about 200 miles from our residence, revealed her “true colors” as a hardcore drug addict.

    We did a deep background check then, including hiring a private detective, and discovered that instead of the 3 charges she’d told us about (and which did show on the Arizona prison website), she’d actually accumulated 51 charges, starting at the age of 21 and going forward. When I told her over the phone (I had visited her twice and we spoke by phone regularly) to tell her she was being cut out of our lives (on two counts, both the addiction and the lying about it), she went ballistic. There was a lot of loud “discussion” over that phone for a while, and we eventually had to block her from calling. Last we heard, she’d been busted again and was back in prison.

    If you’d like me to look up your Jennifer in a bit more detail, feel free to drop me a private email with her full name to: azborderfort@hotmail.com

    An email address in the letter will result in…yes, exactly nothing. Inmates are generally not allowed to email directly to a civilian’s email address but must go through one of the email vendors servicing that prison. But I’ve not heard of a girl being punished for a correspondent including an unauthorized email address.

    Yes, Jennifer can write about her crime if she chooses to do so. In most cases, outgoing mail (FROM the prison) is not even inspected while incoming mail (TO the prison) is looked at for possible contraband such as hallucinogenic drugs in the glue of stamps or envelopes or an amazing number of other possibilities.

    The regulations on the amount of pages in a letter depends entirely on the state and can change at a moment’s notice.

  52. Thank you. I sent you the email.

    A letter with 4-5 pages is okay? I cannot reduce the letter to less than 5 pages. And I do not want to sent 5x 1 letter.

    I use my address but I think the risk is very low that they will stand in front of my door in the future.(I send intotal letter to 9 women). But my main interest and my strongest feelings are for Jennifer. The letters for the other women are only 1 page with less information about me. when Jennifer will stand in front of my door in the future I would be happy.

  53. did you know the case of Lee Grace Dougherty? I saw her profile now on almost every penpal website. Very dangerous for people who send her a letter. Is it in such a case not better to inform the authirities? What do you think? I am not a victim of her but in several forums there this informations. She is the boss of a very criminal and violent gang (even she is in prison).

  54. Four or five pages should go through okay in most states.

    Was not aware of Lee Grace Dougherty. One look at her pen pal profile(s), however, and I instantly recoiled. She would never get access to me or mine because I wouldn’t touch her with a ten foot stick. There are plenty of people who aren’t able to spot such things up front, but the fact that Dougherty is bad news practically shouts at me from the page(s).

    But informing the authorities is not something I would normally do unless my family was under direct threat. Most of the time, in my book, it’s a waste of time.

  55. You are the expert. What are the alarm signs in the profile of Lee Grace Dougherty? Before I send a letter to a woman I check the name online (details about the crime, feedbacks in forums) and I try to make a research but on her website it was not so clear for me. It was more a bad feeling and not details of the profile.

  56. Is it really possible that a letter from europe needs more than 2 weeks (From Germany to Albion (NY)? When I order something in the USA is needs only some days. I got the confirmation that the letter was 29.07.2017 in New York city.

  57. Jeremy, I was short on time (as usual) and only quick-scanned Dougherty’s profile, but:

    1. Her appearance was enough. I can’t read every woman “on sight” from a photo, but some are so powerfully negative there’s no mistaking it, and she is one of those. Her eyes alone hit me what a shot of pure nasty.

    2. In her profile, one thing I do remember is that she states, “Some men are into control but that does not work for me.” There’s nothing wrong with not wanting to be controlled in a relationship; “different strokes for different folks” is an old saying that really does apply couples as well as individuals. But the way she put it right out there, up front and in your face, hit me wrong. I can’t tell you exactly why it did that; it just did.

    I don’t know why your letter took that long to reach New York, not having any first class mail correspondents overseas. I do know that when I order something online from Europe or India, either one, it sometimes takes 3 weeks or so to reach me.

  58. Hi,

    I hope you’re fine. I’m sorry that I have not reported to you so long.

    I am now only in contact with one woman.
    She sent me until now four very nice letters and photos.
    I am only a little bit confused. She told me that she had only 5 visitors in the last 6 years. Online I found the information that she is in prison since 2014. Earliest release date end 2020. Her sentence: 60 month = 5 years

    Is this really possible? You know the American system very good. What do you think. Maybe I am only bad in mathematics. I do not think she’s lying. Or maybe she was a long time in prison before the trial? In Germany they reduce this time from the sentence. I am very interested in your opinion. (I sent you as well an email)

  59. Thanks for posting your question.

    Note: I couldn’t find the email you sent me. Don’t know why; I looked through my SPAM folder and all that.

    About your one remaining pen pal lady: Something is definitely not quite right. I have no way to know if she’s lying or not about her six years in prison, but with a five year sentence and having been incarcerated, her earliest release date should show 2019, not 2020. As for the possibility of her having been in jail (not prison–prior to conviction, people being held for trial are usually in jail) for a long time before officially heading to prison…hm. Three years in jail is NOT the norm; it would have required some really unusual circumstances. Unless she was a repeat offender and she’s thinking of two different sentences, running them together…overall, I have to admit I’m a bit puzzled, too, and would count that as a “yellow flag,” worthy of additional caution going forward. Were it me, I might simply ask her about that–I’ve never hesitated to let pen pals know I’ve looked up their online prison stats…while being aware that if she IS fibbing, her explanation will probably sound pretty believeable. πŸ™‚

    However, the part about having had only 5 visitors in the last 6 years is not surprising at all. We’ve known countless inmates who got NO visits at all, from anybody (even family), EVER. In fact, our one remaining very good friend has had only ONE visit in roughly that amount of time (six years) which was me, when I went to see her in 2015. Not because I don’t want to visit more often, but the trip is long, expensive, and I simply can’t be away from my disabled wife for any length of time these days.

  60. First of all, I want to thank you for writing all these tips! They have been very helpful to me as I compose my first letter. I had two questions:
    1 – This is a more specific question. Any tips on how to end a letter? Is it better to be more formal or casual? Any go to phrases you would suggest?
    2 – This is a more general question. Is it better, if one is just interested in a friendship, for a person to write to an inmate of the same gender? I was wondering how much difference it makes when it is a woman writing to a man. I am interested in what your thoughts are on that.

    Again, I really do appreciate your article.

  61. Hi, April–and thanks for commenting. It’s the comments that keeps these pages alive. To answer your questions:

    1. I always make my final paragraph pretty casual but get “slightly” formal by signing off with “Sincerely” (and my written signature, first name only but below that my full printed name).

    2. Friendship. It’s been my experience that gender doesn’t matter because whether you write men OR women, the relationship possibility will usually raise its head. Quite a few inmates are either bisexual or willing to play that role if it’s to their benefit–as in, “Hey, I’m game.” Example: In late 1996, mere weeks before my wife and I got to know each other, I placed an ad in a Nevada newspaper seeking prison pen pals. The ad was placed under “Men Seeking Women.” I received replies from fourteen women–and six men!

    Bottom line, nearly all of them (with one spectacular exception) had lost all support from civilian sources. Family had given up on them, former lovers had shied away, and they were inexpressibly lonely, without resources, and looking hard. NOTE: A significant percentage were also looking to SCAM their pen pals, so keep that in mind as well. But there are some good people behind bars, too.

    CAVEAT: I’ve never written for “friendship only” so my knowledge in that specific area is limited.

    And finally: Thanks for appreciating the article. Made my day. πŸ™‚

  62. Thank you so much for your reply, sir. I am in contact with two people currently, thanks to your advice, a man and a woman. My uncle was in prison for many years, and I remember how he always talked about how in despair he felt behind bars, even with my dad keeping in contact with him. I do wish to support those people who have none by being pen-pals.

    At the same time, I am wary as I have come to realize that I am evidently “very” young and worry that I will be slow to recognize a scam. Do you have any tips on how to see these? Or will it be fairly obvious? (I know sending large amounts of money is a big one; but is asking for small amounts of cash or pictures suspect?)

    Last question (I think). I had read one of your earlier comments and read that opening up a P.O. box was not a bad idea; I went and did so. I realize though I may have to change addresses in the next few months. Do I need to just mark a different return address on the envelope or would you suggest that I specifically inform my pen pal of the new address change (or P.O. box change, in my case)?

    Sorry for the kinda dumb questions but I thank you for taking the time to answer them.

  63. Thanks for checking in, April. It’s good to see your correspondence going well.

    It’s best to specifically inform your pen pal of the new address change (or P. O. Box change, as you say.)

    About scams: You pose a very good question that requires a complicated answer. I’ll do the best I can.

    1. Some scams are pretty easy to spot. Any pen pal who begins discussing his or her need for money, in whatever form, is best viewed as a red flag. Ditto for an obvious push to go farther in a relationship or perhaps provide a place to live when the inmate is released from prison.

    2. However, other scams can be extremely subtle and difficult to spot. The best way I’ve found to spot them is to stop and think after reading each letter, deciding, “What does this letter FEEL like? Is there ANYTHING in it that, when I sit down and think about it, makes me feel uncomfortable?” Pam and I were scammed a few times even though both of us had decades of tough “street experience” behind us and you’d think we’d have seen the danger signals sooner than we did.

    3. There’s a third category which is very, very tricky to see coming. That’s when an inmate CHANGES over time, usually as a result of long, long years of incarceration. I’ll give one example: Jennifer, who corresponded with us for more than ten years. When we first got to know her, she was still young (25) and had been incarcerated since the age of 16. She grew up n prison, basically, what they call a “jail baby.” And she was the sweetest thing in the world, even after 9 years behind bars.

    About 8 1/2 years later, she nailed us (over a period of time) for a significant chunk of change.

    She would never have done that in the early years, so what changed? Simple. Instead of 9 years behind bars, she had progressed to more like 18 years behind bars…immersed in criminal culture the entire time. It was like she’d finally gained her PhD degree in criminal behavior, but since her demeanor toward us was well practiced and no different, our guard was down.

    All that sounds kind of discouraging, right? And it can be. But that doesn’t mean the inmates don’t need contact with the outside world. Those who write them simply need to understand the world in which the inmate lives.

    Note: Your questions are never “kinda dumb.” Some of my answers may be frustratingly incomplete, though.

  64. Thank you once again; your reply has really helped me.

    I am curious, though, if you don’t mind me asking, what was your next step if you ever read a letter and felt uncomfortable? Did you keep up the correspondence and just became a lot more wary? Did you confront them outright about whatever made you feel uncomfortable, or decide to end the correspondence? I know that really depends on the situation but is there a general “better” way to respond to potential scamming?

    I will certainly keep what you said in mind.

  65. Hi,

    I’ve been wanting to write to an inmate for some time now but I’m afraid they won’t reply because of my age. I’m 18 years old, turning 19 this month and maybe, I’m thinking, they will deem me too naive or something of the sort.

    I hope my question hasn’t been asked yet!

  66. Claire, Fred passed on a few months ago. You probably will not have a problem getting one to reply to you. They seem to like the naive, they will try to talk you into sending them money for their commissary, don’t do it though. Be careful, because they will take advantage of your youth, if they see a way.

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