What do you think the purpose of a penpal is? Someone to vent to? Share laughs with? Build a connection? For some, it’s all of the above. But let’s be honest—penpal relationships can be tricky, especially when a few bad apples spoil the bunch. It frustrates me to no end when I see friends and fellow inmates take advantage of women they meet through penpal websites. This behavior not only damages those relationships but also gives all of us behind bars a bad name.

I’ve got a friend—let’s call him “John”—who married a woman he met on a penpal site. At first, it was beautiful; we were all happy for him. But now? His interactions with his wife mostly consist of him asking her to do things: “Call this place,” “Email that person,” “Send me this.” It’s like she’s his personal assistant! And if she doesn’t do it fast enough? He gets mad. Love should never feel like an obligation. Acts of service might be his love language, but it’s manipulative to demand or guilt someone into doing things. Love is about gratitude and mutual respect—not making someone feel like they’re only valued for what they can do for you.

Then there are the ones who treat penpals like ATMs, constantly angling for food packages or money. Let’s be real—staying connected with someone in prison can get expensive with phone calls, emails, and postage. But that’s no excuse to exploit someone’s kindness. These users give all of us a bad rep.

Not every man on a penpal site is like that, though. Many of us are genuinely looking for friendship, emotional support, and meaningful connections. We don’t want to take—we want to give. Whether it’s lending a listening ear, sharing stories, or just being a source of encouragement, inmate penpals can offer unique perspectives and companionship. Think about it—where else can you connect with someone who has the time to truly listen and appreciate the little things in life?

So, if you’re considering writing to someone in prison, don’t let a few bad experiences scare you off. There are plenty of genuine people looking for real connections. And if you’ve had experiences—good or bad—I’d love to hear about them. What would you look for in a penpal? What do you think makes a great connection?

Shoot me an email at jiovani.jsantiago@gmail.com and let’s talk. Your story might help someone else find their perfect pen pal match.

Contact Jiovani Santiago at jiovani.jsantiago@gmail.com

Learn more about Jiovani Santiago by reading his pen pal profile at PenPals.Buzz

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