Writing A Friend In Prison After 13 Years

One of my best friends in high school is in prison for doing something awful. He was on the run for 2 years and has been in prison for 7 years. I haven’t spoken to him for longer than that – maybe 10 or 12 years? Let’s just say 13 years. I have been wanting to write him a letter but I don’t really know what to say. I’m not even sure if he wants to hear from me at all. We weren’t exactly on the best terms after high school. Here’s the story on why I’m writing a friend in prison.

I had a crush on my best friend in high school.

We met freshman year. I had just moved to a new school. He let me sit with him in math class. He was nice. We talked a little every day. We loved the Resident Evil video games. Eventually we started hanging out after school and at each others’ houses playing video games. We were really good friends for a few years. About a year or so into our friendship, I was crushing on him. Eventually I told him and it was not cool. Being gay in 2001 was sort of like awful. He stopped talking to me.

Here’s the thing: up until the point that he dropped me, he was really nice and cool. He was nice to other people, at least from what I remember. He wasn’t a bully. He liked X-Men and Super Smash Bros. He liked wrestling. He had a dog. He had values. His older brother was really important to him. If I needed him he was there. He fended off other bullies for me from time-to-time.

He bought me this X-Men 2 dvd for my birthday once:

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After high school we made up and talked a few times, then he did something awful and went to prison.

I want to write my friend in prison a letter.

I want to write him a letter, but I don’t know why. Here’s the other thing: our friendship was very short compared to other friendships I’ve had. I had friends in high school after he dropped me that were my friend much longer. I’m not entirely sure why I still think about the short friendship as if it was the best thing ever I had. I don’t have any romantic feelings for him anymore. To be completely honest I’ve seen his prison photos and I’m not attracted to him at all anymore either. But, I miss having his friendship. Or, maybe I miss feeling like one day we will be good friends again. I used to feel like that before he got charged for the awful thing.

So yeah, anyway, I’ve decided to write him a letter.

What do you say to an ex-best-friend in prison?

I don’t know what I’m supposed to say. I can’t bring up the old crush because what if someone finds the letter and gives him a hard time about it? We haven’t spoken in like 13 years so I don’t even know if he’ll want to read the letter in the first place. I also don’t know anything about him anymore. I doubt he still enjoys playing Resident Evil. From what I can tell, this limits our conversation to something like:

“Hey, what’s up? Remember me? You’re in prison and that sucks. I’m not in prison and I’m in grad school. Okay ttyl.”

Yeah that’s pretty much all I’ve got. Writing a friend in prison you haven’t talked to in 13 years is hard.

I could just talk about what’s been going with me, but why would he care really? I could talk about some of the good unique and interesting times we had, but I really can’t think of anything crazy that happened. There were no super funny stories or anything. There’s just us playing Resident Evil 2 and Super Smash Bros.

I don’t know. I don’t know why I want to write him and I don’t know what I want to say. I don’t know why I’m blogging about this and I don’t know if best friends are even real anymore anyway.

Have you ever written a friend in prison?

Have you? What about an ex-friend who you sort of made up with before they went to prison, but not really and you’re not super sure about it and it’s awkward? I suppose I could ask him that in the letter. So far that’s:

“Hey, what’s up? Remember me? You’re in prison and that sucks. I’m not in prison and I’m in grad school. I remember we weren’t speaking for a long time in high school and then I remember we talked after high school and sort of made up. Did we? Are we friends again or not? Okay ttyl.”

Well, at least I’ve got somewhat of a paragraph. Writing a friend in prison who you’re not sure is a friend anymore is awkward.

Have you ever written a stranger in prison?

Don’t they have things like pen-pal services for prisoners? Aren’t there people who write prisoners because it’s nice and it helps them feel less lonely? Are those real or am I just making them up? Maybe I heard about them in a movie or something. If they are real, maybe I should start with writing strangers first?

I used this app called Slowly a few times to write people from other countries. I was kind of cool because it simulated real mail. It took days for the mail to arrive to their inbox and more days for you to get your response back. But like most things in my life I didn’t keep up with it and I haven’t used it since like May. I guess I should respond to some letters on there.

Anyway, I can’t write him like I don’t know him at all because that would be really weird. I know him, or at least used to, and we have a history.

What he was charged for doing was really awful.

I’ve said this a few times, but it is a factor in how I approach my letter. What he did (at least according to the system) was super bad. Like, really bad. I know that there are secretive groups of people in prisons who watch the mail and watch for people who write certain people. These people have people who check up on these people to try to figure out how they’re associated with them. I’ve heard of them causing trouble for some of these people. I definitely don’t want that. I also don’t want someone giving him a hard time when they find out a gay dude is writing him.

I just want to write him because I used to know him and I miss having a friend like him. Well, the cool him. He really was very nice before.

At some point after he dropped me, he joined the military and got really buff which was nice, but then he got into drugs and stuff. I didn’t know him during those times. I only knew him when he was skinny and played video games and watched X-Men. We shared Nintendo Power and Game Informer magazines. We called each other all the time to help each other get through sections in video games because you couldn’t just look up a let’s-play on YouTube back then.

Anyway, I’m not sure if I should bring up what he did or not in the letter. Probably not.

So I’m writing a friend in prison a letter but I don’t know what I’ll say.

I’m going to write him because if I don’t I’ll always feel like I should have. The letter will probably be short and awful and stupid, but I’m going to do it anyway. It might cause trouble, it might not. I hope it doesn’t. Seriously, have any of you ever written a letter to a friend in prison after a long time? How did you approach it? Why did you write them after so long? Please comment below and let me know because I’m kind of needlessly stressing about it. Am I crazy for writing a friend in prison after 13 years? I mean ex-friend or a maybe friend?

Me having my coffee this morning. When I’m done with my coffee I’ll get started on the letter.

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Update: I wrote the letter. Now I just have to figure out how to address it. I doubt he’ll actually write back, but at least I got this out of my system.

By Eric Shay Howard

Eric Shay Howard lives in Indianapolis. He's a teacher, a literary editor, and writer. He's a graduate student in the Bluegrass Writers Studio MFA in Creative Writing program at Eastern Kentucky University. He also has MBA and BA degrees.

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