Order of Malta


Difficult Prison Pen Pal Questions and Suggested Answers


Pictured above: Connecticut (SWN) Area Pen Pal Program meets regularly for pizza..and to discuss best practices.

This story is the seventh in the “Best Practices” series from the American Association’s Prison Ministry Committee. Read part one here, part two here, part three here, part four here, part five here, and part six here


Frequently Asked Questions and Suggested Answers for Prison Ministry Pen Pals

By Emily D., Twin Cities Pen Pal Prison Ministry, MN

1.My pen pal has been making comments about romance and intimacy that are making me uncomfortable. How should I respond?

While these kinds of comments are uncomfortable to read, it’s not entirely uncommon for pen pals to reach out in this way. Their isolated state makes them very prone to loneliness, and many of them are seeking relationships with those on the outside. However, it does mean that you’ll need to reset the boundary and remind them of the application they signed.

Suggested Response: I want to remind you of the agreement you signed as part of your application to this pen pal program. It states that you agree not to discuss romance in your correspondence. I understand your hope to be in a relationship, and it must be so hard to be seeking this in a place that makes everyone feel so alone. If romance continues to come up in your letters, I won’t be able to continue to be your pen pal because it’s not allowed as part of the guidelines in this ministry.

Also, it is always okay for the volunteer to decide that s/he simply isn’t comfortable with the correspondence and no longer wants to write to this particular pen pal. If this is the case, please notify us. We will write to your pen pal to put closure on the match and offer you a different match, if you’d like.

2. My pen pal sent me the name and contact information of his lawyer and would like me to contact her because she isn’t responding to his letters. He needs legal help before his next court date. How can I help?

This is a tough question because we inherently want justice and fair treatment of those in prison. However, it is also part of the pen pal agreement that volunteers cannot contact any family members, attorneys, or others on the outside on behalf of their pen pals. This rule is in place to protect our volunteers’ identities and prevent them from getting in the middle of legal issues or family dynamics in which our ministry does not train volunteers to participate.

Suggested Response: Because of the agreement we signed, we need to understand that I cannot get involved with attorneys or family members. (“Blaming” the pen pal program guidelines and agreement is a way to NOT make it personal. These are simple rules that you didn’t make but must follow if you want to continue correspondence.)

Please contact Emily if your pen pal continues to push on getting you involved with legal issues after you’ve reminded him or her of the rules. We will write a letter to your pen pal.

3. My pen pal’s letters have become increasingly negative and he sounds very desperate, almost threatening. I’m worried that he might hurt himself or someone else. What can I do?

Letters from your pen pal might be a rollercoaster of ups and downs when it comes to emotions and moods. This is the nature of incarceration, and self harm can be a real concern. If you are worried about this, you should reach out to Emily. She will call or email the chaplain at the facility and ask if he/she can reach out to your pen pal in response to some concerning communication received through our program.

You can also encourage your pen pal to reach out to the chaplain. People in prison aren’t always made aware or easily provided with the resources available to them.

Sometimes an encouragement from you is just what they need to take action. It’s hard not to take on a feeling of responsibility for solving the problem, and your letters mean more than you realize in terms of helping your pen pals increase in self esteem and self worth.

4. My pen pal keeps asking if I will email him since it doesn’t require as much money as postage and email communication is much faster. Should I email him?

As more and more facilities are starting to offer email-like communication, many of our pen pals have begun to ask their volunteers to communicate this way instead of through handwritten letters sent in the mail.

The only platform that Twin Cities PM has vetted and approved is jPay. There are serious risks associated with digital pen pal communications.

We have two or three volunteers that have transitioned to using jPay as their main form of correspondence. Using jPay does mean that we have no way to track and document communications.

Please contact Twin Cities PM if you choose to transition to jPay so they can make note of it in the database and answer any questions you might have.

5. My pen pal would really like to continue corresponding with me after he is released next month. He sent me the address of his new apartment so that I can reach out. How do I respond?

We have a handful of volunteers who continue to write to their pen pals upon release. Continuing this relationship during what is typically a very turbulent time for our pen pals can be very helpful and provide some stability and needed encouragement. If you do choose to continue writing, we require that you still adhere to all the pen pal guidelines that ensure confidentiality like using our PO box for all mail, maintaining your pseudonym, and reaching out if you are ever feeling uncomfortable. You get to decide if you’d like to continue writing. It is also fine to end correspondence and decide you’d like to be matched with a new pen pal.

6. My pen pal is frustrated that he can’t write as much as he’d like to because of the cost of supplies (envelopes, stamps, paper), and he’d like me to send him stamps or transfer him a little money so that he can continue writing.

It feels like nothing to send a couple stamps or a few dollars to our pen pals, especially if it means they can have access to writing material. However, this is never allowed. The mailroom will confiscate the stamps, so they won’t make it to your pen pal anyways. Sending money of any amount always has the potential to put incorrect expectations on the nature of the pen pal correspondence as well as opens the door for manipulation. Keeping money out of your relationship protects both volunteers and the residents from inappropriate expectations and assumptions.

Suggested Response: Again, remind your pen pal of the agreement that you both signed.

7. My pen pal keeps asking for me to send pictures of me and my family because he feels like I’m not a real person without being able to see me. And he says he feels like he’s being tricked by my using a fake or incomplete name

It’s easy to empathize with this frustration especially if your pen pal is sending pictures of himself and family to you. Faces and names are such personal parts of who we are. This request is often resolved with a one time response that restates the boundary that your pen pal already knew about because he signed an agreement.

Suggested response: I understand how frustrating it is to not receive pictures or my real name. In order for me to be able to continue writing to you, I do need to adhere to the rules the Order of Malta listed and had me sign.

You can choose whether or not to explain that the rule is in place to maintain safety and confidentiality for volunteers.

8. My pen pal frequently talks about being lonely and requests that I write more letters. He thinks he should be receiving a lot more mail from me, especially since I’m the only one who ever communicates with him on the outside.

The amount of mail residents write to our volunteers varies greatly. Some are sending letters each week while others are sending once every couple months. Regardless of the frequency your pen pal is writing, you are only expected to write once a month for 12 months. This suggestion is meant to make this ministry doable and not overwhelming for our volunteers. We want to protect your time. Some volunteers do choose to write more than once a month which is also just fine.

Suggested response:  “I’m sorry that you wish I was sending more letters, and I understand that it feels like too much time passes between them. The Order of Malta recommends writing once a month, so I will continue to do so. Let me know if you would be interested in being assigned another pen pal so that you could receive two letters per month. Sometimes the ministry has enough volunteers that this is possible.”

Please let us know if your pen pal would like to write to more than one volunteer. We are usually in a place with volunteer applications where this is possible.

9. I write to my pen pal faithfully and I haven’t heard from them in months.  Should I just quit writing to them? 

There are a variety of reasons that your pen pal might not be responding that can include lack of access to resources like money for stamps, envelopes, and paper. He might also be encountering various challenges like illness or an emotionally difficult time. While it’s also possible that he has been released or transferred to a different facility, we’ve had several volunteers write for months without a response only to receive a letter from their pen pal thanking them for the encouraging letters and providing the reason for their inability to write.

We encourage all of our volunteers to write once a month for 12 months regardless of response rate.

You can always reach out to us with questions if you suspect your pen pal has been transferred or released. We can check for you.

For more information regarding the Pen Pal Program, please click here

Order of Malta

American Association, U.S.A
St. Patrick’s Cathedral Parish House
14 E 51st Street
New York, NY 10022
(212) 371-1522