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)

43 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.

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