“It was difficult to admit I had feelings for a prisoner”: Here’s what having a prison pen pal is like

“I was looking to understand someone in a situation that was completely opposite to mine.”

While the genre of true crime may feel relatively new, our obsession with felonies dates back to 1600, when members of the clergy would plaster details of illegal activity on town walls for all to see (gossips). Now the multimillion-dollar industry includes tell-all books, documentaries, interviews and podcasts dedicated to our fascination with crime.

Psychologists speculate that to best protect ourselves from potential threats, we obsess over knowing the ins and outs of cases and memorising key points so the same thing won’t happen to us. The recent prison release and overnight fame of Gypsy Rose Blanchard is a prime example that for true crime audiences, parasocial relationships run deep.

Interested to hear how others navigate the world? Head to our Life section. 

During her time in prison, Gypsy says she received over 250 love letters, one of which came from her now-husband Ryan Anderson (and yes, the D is fire). I wanted further insight into what a relationship with a prisoner was like – not the kinds of ones you see in hyperbolic retellings (like Zac Efron’s Ted Bundy).

Instead, I wanted to understand the people looking to form meaningful connections with criminals on the road to rehabilitation. To find out more, I asked Jill*, 22, who has been writing to prisoners for the last two years.

Can you tell us a bit about yourself and what got you into the prison pen pal landscape?

I’m a student studying science. Growing up in a relatively conservative family, I never knew of anyone who had any convictions or [had] been to prison at all. The importance of following the law was drilled into me as a child. Of course, I also knew that a crime doesn’t define someone. I was looking for connections and to understand someone in a situation that was completely opposite to mine.

How did you find out about emailing prisoners?

I always knew people had prison pen pals. I searched for people looking for someone to talk to and Write A Prisoner came up. I actually found out that inmates have to pay $40 to be listed.

How many pen pals have you had in total?

I’ve had three prison pen pals over the course of the last two years.

How do you choose who you want to write to?

Prisoners get to write a short bio about themselves. I picked my pen pals based on their profile description and their crime. I specifically picked crimes that I could see as ‘justifiable’ and within reason. I never picked anyone who had performed acts of neglect, abuse, drug-based violence, robbery etc.

What are the types of relationships you’ve had and for how long?

I’ve had friendships spanning several months with two of the prisoners. Our emails consisted of… advice, their time in prison and their lives before incarceration. I had one pen pal on death row who was just happy to hear what I got up to in the past week.

I never saw it as a philanthropic relationship where I helped someone in need, but rather a relationship where I could learn from their situations and reasons for their crimes.

You’re currently in a romantic relationship with an inmate, how did that come about?

I asked if she wanted any pictures to hang up on her wall (I meant scenic or aesthetic). When she said, “Hell yes, I hope they are of you!” I was like “Wtf, you want pics of me?”. I asked if she wanted bikini pics, she said yes and it continued from there.

It was difficult and sort of embarrassing to admit that I had feelings for a prisoner, especially since I was the one who had the feelings first. I went into it thinking I could never have a relationship with a prisoner and surprised myself.

What attracted you to her?

I was already physically attracted to her when the emotional feelings began. I admired her strength, the way that way would protect people, and her ability to give life a kick in the ass.

What have you learnt since being in communication with inmates? Are there any surprises or things you found difficult?

The actual prison system itself was the biggest shock. Is it bad that I always thought American prisons were empty jail cells and people were regularly beaten by guards ([although] this was true in the case of my pen pal on death row)? But as for my current pen pal – she surprises me with the programs on offer.

There are parenting, writing and trauma classes, with accommodations made for her Native American faith… [there are] things like sweat lodges that have a qualified spiritual pipe carrier who goes into the prison, ceremonies, walks, feasts. It’s the bare minimum but again, it surprises me.

Would you recommend getting involved in Write A Prisoner?

I would totally recommend getting involved with Write A Prisoner, there are some meaningful connections to be made with people who you wouldn’t usually get a chance to speak to.

That being said, be careful of [their] intentions. It’s mandatory to have their legal crime listed on the website (which has to be vetted) but the nature of the crime itself isn’t [mandatory], i.e. sex offenders, child neglectors and people who have murdered their own children. These are the types [of crimes] I avoid because I personally cannot justify talking to someone who has committed them.

*Name has been changed for privacy.

For more on prison pen pals, head here.