When people hear I’m in a relationship with a man who’s incarcerated, the reactions fall somewhere between disbelief and pity. Sometimes curiosity. Sometimes judgment pretending to be curiosity.
“Why would you date someone in prison?”
“Don’t you want more for yourself?”
“I could never do that.”
And every time, I think the same thing: You have no idea what you’re talking about.
Because this isn’t a Hallmark movie. And it’s sure as hell not a fantasy. It’s a relationship—just like anyone else’s—but with every possible difficulty dialed up to eleven.
It Didn’t Start With Handcuffs
We didn’t meet through some prison love website. I wasn’t seeking it out. A friend mentioned a pen-pal program. At first, I just wanted to be kind. Send a letter to someone who hadn’t gotten mail in months. I didn’t expect anything back. But he wrote. And I kept writing.
What started as curiosity became connection. Then emotional intimacy. Then love.
He told me the truth—about what he did, how he ended up where he is, and who he used to be. He didn’t sugarcoat it. But he also didn’t ask me to rescue him. He just showed up, emotionally and honestly, every time I needed him.
That was more than I could say for half the guys I’d dated on the outside.
The System Becomes Your Third Wheel
What nobody tells you about being with someone in prison is that your real relationship isn’t just with your partner—it’s with the prison system itself.
Every part of your connection runs through red tape:
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Phone calls? Up to $1 a minute, monitored, recorded, and cut off mid-sentence when count time starts.
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Letters? Searched. Sometimes lost. Sometimes rejected for reasons that make no sense.
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Visits? Dictated by dress codes stricter than private schools. I once got turned away for wearing a long-sleeve shirt with a zipper. I’ve been told to change clothes because my bra was underwire. I’ve had to explain I was menstruating to a male CO just to be let inside.
Visitation is rarely romantic. It’s long drives to nowhere towns, vending machines for dinner, and holding hands across a cold metal table while a CO watches from the corner.
And don’t even think about making plans around it. Lockdowns happen with zero notice. Your entire weekend can be canceled without explanation. Just like that.
The Emotional Load They Don’t See
Loving someone in prison is like building a house on quicksand. Just when you think you’ve found stability—he’s doing programs, working a prison job, in a good mental space—boom: someone fights in his dorm, and he’s locked down for 23 hours a day.
And suddenly you’re the emotional anchor. The therapist. The secretary. The banker. The entire support system.
You have to be okay even when you’re not okay—because he needs you to be strong. You’re often the one paying for calls, sending money for commissary, emailing pictures to remind him he still has a life outside of razor wire.
People don’t get how lonely it can be. You’re in love, but you’re alone. You celebrate birthdays on phone calls. You spend Christmas in a waiting room. You fall asleep to silence, not someone breathing next to you.
And yet—there’s intimacy there, too. Forced by circumstances to really talk, we got to know each other more deeply than I ever had in “free world” relationships. There’s no room for games. No hiding. You learn to listen and be present in a way most people never do.
The Judgment Hurts More Than the Distance
The hardest part isn’t the distance. It’s the way people look at you when you say you’re with someone in prison.
They assume you’re broken. Or being used. Or settling for scraps.
But here’s the truth: I’ve never felt more emotionally cared for. I’ve never had someone speak to my soul so clearly. And I’ve never had to fight so hard just to be allowed to love someone.
We carry the stigma of their sentence like it’s our own. People think they know your whole life from that one fact—he’s in prison. But what they never ask is what he means to me. Or what I’ve learned about myself through this love.
The Unseen Realities
There are things you just don’t realize until you’re deep in it:
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The financial burden of keeping a connection alive across walls and wires.
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The fear every time the phone rings late at night.
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The humiliation of being treated like a criminal just for showing up to visit your partner.
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The way time stops during a lockdown—and how powerless you feel when he disappears into silence for days.
But also:
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The way his letters smell like the paper of your childhood journals.
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The way his voice softens when he talks about your future together.
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The way you find strength you never knew you had—because you have to.
And Yes, Sometimes It Ends
Some prison relationships don’t survive release. The structure and safety of confinement vanish, and real-world pressure sets in. I’ve seen women wait years, only to be ghosted the moment he got a taste of freedom.
It happens.
But that doesn’t mean the love was fake. Or that we were fools. It just means life is complicated. Especially life that starts behind bars.
So Why Do I Stay?
Because this man makes me feel more respected, seen, and emotionally safe than anyone ever has.
Because love isn’t always convenient—but that doesn’t make it any less real.
Because I believe in redemption. Because I’ve watched someone grow, evolve, and take accountability from the hardest place on earth to do it.
Because in a world that rushes past people, that discards them the minute they mess up, I choose to be someone who stays.
And because, quite frankly, I’m not interested in a world where love is only considered valid when it’s easy.
To those on the outside looking in:
I don’t expect you to understand.
But don’t mistake your lack of understanding for my lack of value.
And don’t confuse my love story with a cry for help.
It’s not perfect. It’s not easy. But it’s mine.
And it’s real.
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