So, you’re thinking about becoming a prison pen pal.
You’ve heard about it, maybe read a story or two, and now you’re curious, like, what do I even write?
Is it safe? Will it be awkward? What do I say to someone behind bars?
First of all, take a deep breath.
You’re not alone in wondering. In fact, before reaching out to incarcerated pen pals, most people have the same common prison pen pal questions.
And in this blog post, we’re answering the most common ones. Let’s get into it.
1. Is it safe to write letters to incarcerated pen pals?
Yes, it can be safe, as long as you take a few precautions. Most penpal writers use a P.O. Box or a secure mail forwarding service instead of sharing their home address. Avoid sending money or overly personal information, especially early in the conversation.
Start with boundaries, stay respectful, and remember, you’re allowed to say no or stop writing at any time.
2. Are there any trusted pen pal services available?
Absolutely. Some well-known prisoner pen pal services include:
- A Way Out Pen Pals (that’s us!)
- Write A Prisoner
- Black and Pink (focused on LGBTQ+ inmates)
- Conpals
These platforms are designed to match volunteers with incarcerated pen pals based on shared interests, age and location. Just make sure the service you choose is transparent and clearly outlines safety and communication guidelines.
3. Where and how can I even begin?
The first step? Decide why you want to write.
Is it to offer support? Share friendship? Learn someone’s story?
Once you’re clear on your “why,” you can:
- Sign up for a trusted pen pal platform
- Browse inmate profiles
- Choose someone you’d like to write to
- Send your first letter through their listed mailing method (some use snail mail, others use secure email platforms like JPay or GettingOut)
4. What can I talk about in my letters?
It might feel awkward at first, but you don’t need to overthink it. Inmates are just people. They appreciate normal conversations.
Here are a few questions for penpals to get the ball rolling:
- What music do you love listening to?
- What are your favorite books or shows?
- What hobbies did you enjoy before prison?
- Do you believe in second chances?
- What’s something you’re proud of?
Just be yourself, stay kind and don’t push for personal details they’re not ready to share.
If you need more suggestions or guidance on what to write, check out our blog post on: How to write a letter to an incarcerated person.
5. What are good questions to ask a pen pal?
Aside from the casual ones above, here are more thoughtful common prison pen pal questions that can lead to deeper conversations:
- What motivates you to keep going each day?
- Have you learned anything surprising about yourself during your sentence?
- What’s one thing you wish people understood about you?
- If you could give advice to your younger self, what would it be?
- What does freedom mean to you?
These kinds of questions can build a strong and meaningful connection over time.
6. Where & how can I find a prisoner pen pal?
Start by visiting one of the prisoner pen pal services mentioned earlier. These websites allow you to filter inmates by age, gender, interests and location. Some sites even highlight inmates who haven’t received mail in a while, so you can make a big impact right away.
Once you find someone who resonates with you, follow the mailing instructions provided in their profile. Most profiles include their facility’s address and inmate ID number.
7. What are the rules for having a prison pen pal?
Rules may vary depending on the prison, but here are some common ones:
- Always include the inmate’s full name and ID number
- Don’t send prohibited items (check each prison’s list)
- Avoid sexual or inappropriate content
- Keep your letters respectful and positive
- Don’t make promises you can’t keep
Following the rules shows respect, not just for the prison system but for the person you’re writing to.
You can also refer to our detailed guide on: Letter writing guide for inmates: Do ‘s and Don’ts
8. How can I positively respond to negative questions from a pen pal?
It’s okay if tough topics come up. Some inmates may open up about their regrets, trauma, or loneliness. You don’t have to have all the answers, so just be honest and compassionate.
Here’s a helpful way to respond:
“I can’t imagine what that’s like, but I appreciate you trusting me with it. I’m here to listen if you ever want to share more.”
Sometimes, kindness means just being there, even if you don’t have the perfect words.
9. What are the benefits and risks of writing to a prison pen pal?
Benefits
- You help someone feel less alone
- You gain perspective and empathy
- You build a human connection across walls and labels
Risks
- Emotional dependency (from either side)
- Misunderstood intentions (especially around romance)
- Potential for inappropriate requests (rare, but possible)
That’s why boundaries are key and why using a reliable service makes all the difference.
10. Should I Write to an Inmate Pen Pal?
See, you don’t need to have it all figured out.
If your heart is in the right place and you’re willing to offer a few kind words to someone society has forgotten, you’re already making a difference.
Summing Up:
See, you don’t need to be perfect to become an inmate’s pen pal. And honestly, it takes courage to take that first step, which can bring up a lot of questions, just like the ones we covered here.
We’ve tried to answer the most common things people wonder about before they decide to write. But if there’s something else on your mind, we’re always here to listen and help.
So whenever you’re ready, or even if you just want to ask something, reach out. We’d love to hear from you.
