Just reading the title, I’m sure you already have ideas and thoughts about what this will be like. What I’m going to say. The type of man he is and the type of woman I must be. You probably have some assumptions about our backgrounds and upbringings. I don’t blame you. If you’d said those words to me fifteen years ago, “I’m in love with a man in prison,” I would have had the same reaction. There’s a reason these things get their own reality television shows—because they’re outside of the norm. They’re taboo.
They’re exciting.
Sure. It’s those things. But it’s also hard. People make judgements—swift ones—without knowing the person they’re making judgements about. As humans, we function off our own biases and knowledge and the fact of the matter is this:
Until you know someone in prison, you don’t know about prison.
It’s fair to say that most people don’t know anyone in prison let alone regularly think about what it must be like to be there. Acknowledging you’ve ignored someone else’s pain is a hard pill to swallow. Most people never even fill the prescription. No one wants to think of themselves as uncaring—and ignoring someone’s pain doesn’t necessarily mean you are. It means you’re human. We aren’t designed to self-inflict pain or naturally want to do things that are uncomfortable. There’s a reason that word exists and there’s a reason we avoid it. By avoiding it though, the pain transfers to someone else. Pain has to go somewhere.
Mental health, food insecurity, educational disparities, the poverty cycle, addiction…all of these things are so interconnected to our prison and judicial system, even our economy as a country. Once it starts, once someone falls prey to it, everything stacks against them. Young men who’d robbed a gas station at seventeen to get money to buy food for their family are still sitting in prison thirty years later. Not rehabilitated. Not a betterment to society. Just, there in pain.
I’d always been interested in social justice and activism—but I was at best a “passive activist.” After the 2016 election and then the events of 2020, I knew I had to swallow the hard pill and start acknowledging what I didn’t know. I had to get out of my comfort zone. I had to challenge how I looked at everything. It didn’t make me jaded, it made me aware. Suddenly, I had all this new knowledge, but I still wanted to know more. I wanted to keep learning and do better for the causes I was passionate about.
The American Prison System isn’t made for rehabilitation. It’s made for punishment and profiteering, and it requires the inhabitants it takes so easily. Without them it wouldn’t stand. If people were educated, had access to health and mental health care, were paid living wages…the prison system as it exists today, would crumble. It’s a game of politics. It’s about money. And the people being swallowed by it? Most of them never stood a chance.
When you put human beings under harsh adversity, they’re constantly living in fight or flight. There’s no free-conscious living anymore. Addictions worsen, mental health declines, the already limited access to education is exacerbated and by the time these men and women come back to society, they’ve been so broken and beaten down on the inside, daily living can feel nearly impossible. And now they’re being forced to claw and fight their way back up to some level of acceptable humanity in society. But society doesn’t make that easy.
Have a felony? Can’t get a job. Oh, you also can’t vote for people who would fight for your rights.
Don’t have an education? Here, take this menial job that will pay you less than a livable wage.
Are you following me here? This system is a cycle made to take people from their burdens of circumstance, put them in a punitive institution designed to keep them down and then make it desperately impossible to live once they re-enter society. And people still have the audacity to wonder, “What the hell is going on?!”
Why.
Can’t.
They.
Just.
Get.
It.
Together.
Already?!
In my bones I knew what I needed to do. I needed to talk to someone who was, or had been, incarcerated because until I really allowed myself to know that world and the residents inside of it, I couldn’t fight for the betterment of it. The truth was, I’d never known anyone who had experienced the system I was suddenly so angry with.
I learned quickly that the prison system wasn’t working in favor of “law and order” or “rehabilitation.” I learned the cards were stacked. I learned the whole thing was broken. Still, while I learned all these things, I only knew them on paper.
At least until I met Bear, then I learned more than I ever expected to.
Writing is something I’ve always done, it’s my ultimate passion and I knew if I was going to drop myself into the deep end, it had to be through a medium I was comfortable with. Which settled things–I was going to find a pen pal.
From the beginning I knew there would be another living, breathing person on the other side of these letters, and that was not something I took lightly. I couldn’t imagine bringing harm or suffering to their life, especially when they were already in one of the most vulnerable positions. I was diligent in my search. I spent an entire afternoon looking for someone who I felt would understand my intentions, who would be willing to share their experience with me, and maybe even someone I vibed with, because ultimately, I was secretly hoping that we’d end up being friends.
One profile stopped me. I’d been scrolling through pages for what felt like hours, and then time halted when I found his. He spoke about consciousness, about the world. He was a college graduate from one of the top three art schools in the country. He was well traveled. He did yoga and meditated. My unconscious biases slapped me hard across the face because my first thought was, “This man is everything a prisoner shouldn’t be.”
There was no more searching, no going backwards or forwards. I needed to talk to him. I needed to know more. I ran background checks, searched court records, pilfered news articles and social media profiles. Whatever information was out there about why he was in prison—I read it. I knew what I was walking into. I knew why he was there, at least judicially…but I wanted to know more, I had to know who he was.
My first letter took days to write before I finally got the courage to hit send. I waited. I tried not to have expectations around whether he would respond, or what he might be like if he did…but I’d be a liar if I said I wasn’t anticipating that first response, that I wasn’t excited—because it IS exciting.
Four days later, I had an email. Not just one–but three. 12,000 words that gave me a peek behind the curtain of his mind.
He’s well read and eager to talk about books and music. He’s artistic and creative. He studies things to his fullest ability. He never stops learning. He’s kind and compassionate. He pays attention to things most people overlook. He cares about people and what they think. He listens intently. To say that he went against the norm was an understatement. He was an outlier. I couldn’t make it make sense that he was there. Yeah, I knew on paper why he was there…except I wanted to know the real why–the underlying turn of events that led him to this current karmic predicament.
The answer wasn’t glamorous. The answer was–it’s life.
It happens. It happens to all of us. Our choices, our decisions, our actions—they all have outcomes. Sometimes we’re fortunate and sometimes we’re not.
What I came to find out and what I appreciated most about him was that he was aware enough to realize that his own actions, his own choices led him to this place. That self-awareness showed me who he was in the center of his chest. He’d learned that even though his actions and choices put him here, those things no longer had the power to dictate who he was or who he would be when he walked out those doors. He’d accepted responsibility and he wasn’t going to let it define him any further.
That perspective was what he wanted to teach others. That they CAN walk through fire and come out the other side. It’s hard work. It requires you to look inward and unearth the ugliest truths about yourself, but when you dig them up and examine them, they can’t grow like they did when they were planted deep in the soil. I’m a firm believer that you can’t teach others about something you don’t understand yourself. You can try, but eventually the ruse falls through and the man behind the curtain is exposed.
When I came into the picture, it had been over a year since he’d started focusing on serving others versus himself…and it showed. He was passionate when he spoke about helping people. I could feel the energy radiating from him when he talked about his Eastern Religion class. He was rehabilitating himself within the walls of a system that would gladly swallow him whole and leave him to rot. He was taking action that would eventually serve him, but that wasn’t why he was doing it. He did it because he wanted other people to feel the same way he did. Awake. Alive. Valued.
And he was doing it all in some of the harshest circumstances.
The more we spoke, the more he solidified my perceptions of him. I’d never met anyone like him. I could listen to him talk about art and music for hours. That passionate fire within him sparked one inside of me. It woke up dormant thoughts and ideas that I’d forgotten about. More importantly, he made me feel.
I’m not talking about the feeling of attraction or romance. Those first feelings were of self. Of me. I felt inspired to write again, to challenge myself, to expand what I was reading, to dig in between my own ribs and learn who I was–what made me tick.
More letters. More phone calls. More artwork. More of him, his soul, who he was at his core. I shared more of myself, opened up, and truly trusted the process of getting to know someone in ways I hadn’t before. In the process of getting to know him, I came to know myself all over again. Things I’d known—my magical thinking, my ideas about a soul’s journey, consciousness all came right into the spotlight because I suddenly had someone who understood. Who saw the same colors I did. Who saw me. Just me.
There’s value in that simple act, in being fully seen by someone. I’ve been loved my whole life. I’ve never felt unloved…but this was one of the first times I’d ever really felt seen.
He could anticipate things about me before we ever spoke about them. He sensed how I was feeling well before he’d call and verify it for himself. It should have been unnerving, to have someone that could see you as if they were watching your every move—but it wasn’t. It was the most effortless sensation. Like every part of my being knew exactly what to do with it. It felt safe. It was as natural as falling asleep and waking up. I let myself lean into these feelings I was having with him. Each day I felt it grow. We were tending to a garden that could only be accessed by the two of us.
At the edges of the garden though, was the system that caged him and the people outside who didn’t understand how this could even come to pass. Both constantly knocking at the gate, trying to gain entrance and prove that you couldn’t possibly fall in love with someone who was incarcerated.
“No one will understand.”
“You’re setting yourself up for heartbreak.”
“It’s a scam.”
“It’s not real.”
For individuals who’ve never experienced it, those things must seem like true statements. People want to understand because when we don’t understand things, when we can’t find a reason, we have concerns. People won’t see the air the same way you see it, they crave explanation and they need to have their anxieties met with resolution and calm.
Loving someone incarcerated doesn’t give you any of that, at least not regularly. There are deep sets with sharp edges and there are easy, cool nights when you forget about the barbed wire and concrete between you. It’s up and down. It’s unpredictable. It’s scary. You can’t give calm resolution when you don’t know what is around the corner. There is a real threat every day. A constant cloud of stress and suffering that he’s exposed to. It’s not a resort—it’s prison. It’s an environment that is designed to break people, and it will if they let it. It’s easy when you’re talking on the phone to lose sight of that. It’s easy to let yourself become immersed in the stories you’ve created with this person.
Through the pursuit to learn more and ready myself for the fight to remedy a broken system, I’d found something bigger than I ever imagined. I found him. Despite what the outside world thought about the situation, I never doubted it. Instead, I chose to trust it. To trust this connection.
When I wrote that first letter, I thought I knew what I was walking into. When it came to what landed him there, I did for the most part.
But loving someone in prison? It’s not like movies or tv. I found myself in the middle of a sharp world that didn’t care about this person in the same way I had come to. Everything was designed to make his life harder, to remove what made him human—the parts that I’d come to love most about him!
I only thought I came into this caring about prison reform. I spoke in favor of the notable changes that needed to happen: more rehabilitative initiatives, less incarceration for non-violent offenses.
Now? Now I know that out of 50 states, 44 don’t have air conditioning in their prisons. I’ve experienced the anxiety of waking up in August to see that it’s going to be 105 degrees and a person I care about will be stuck in a concrete box that’ll get to 125 degrees by noon. At one point, his walls were literally sweating.
I’ve experienced what it’s like to hear from others that there’s been a disturbance in the building where they live. You can’t text them. You can’t call and check on them. You have to wait for them to contact you. You have to create a checks and balances system beforehand. “If you haven’t heard from me in this amount of time, call. Throw a fit. Demand an answer. Please make sure I’m alive.”
I know what it’s like to anticipate a phone call and not get one and then spend the rest of the night and the next day worrying yourself sick about whether it was just the WiFi being down again, or if this was the time he was caught in the middle.
Those are just the concerns that we face while he’s inside.
What happens when he gets paroled? I’m half a country away – will he come here? Can he come here? How would that work? I’m sure there’s a process…I should look that up. I can’t pick up and move to Texas, not that I’d want to because let’s be honest—it’s Texas. Does that mean that it ends? Does it keep going as long distance?
Long distance rarely works with both people being out of prison. Statistically speaking, relationships that start when one person is incarcerated fall apart within the first year of them being back in society. That won’t happen to us though, right?
A lot of people in the carceral system do well because it’s structured, it’s routine. What if the structure of being inside is what is holding him together and the constant chaos of my outside world causes him to fall apart?
The list goes on and on and on. Trust me, if there is a “what-if” scenario…I’ve thought about it. I’ve worked it all the way through to conclusions that are at worst, devastating and at best, delusionally optimistic.
But you pause.
You breathe.
You learn.
I’ve learned that loving someone who is incarcerated doesn’t mean you suddenly become willing to turn a blind eye to the obstacles you’re going to face because they may not be right in front of you in that moment. It means you’re willing to support them through the obstacles when they come around; and they will come around. It becomes a conscious decision to help them keep going when it feels easier to give up.
Being willing to love someone incarcerated means you’re willing to fight for them. It becomes less about fixing the broken system and more about making sure they survive it. To do that? To really fight hard requires you to educate yourself on their world, to believe in their recovery, in their rehabilitation and not continue punishing them for their past. Prison does enough of that already. If you’re going to fight to change it for the better—you have to learn it from the inside, through their eyes and start there. That’s what it means to love them unconditionally. You’re willing to look towards their future, to hope for them.
Hope is where you get to the heart of things. Hope is where you find out what it really means to love someone fully. When we love someone, we all hope for the same things, whether they’re incarcerated or not.
We hope for happiness. For connection. For feeling seen and being known by someone else. For blue skies and warm breezy nights. The best I can hope for us? Betsy and Bear?
I hope we land somewhere safely among the clover in the garden we’ve grown together. He gets to take an uninhibited free breath, I get to see him take it and that garden gate the world kept knocking at? It’s wide open for us.

