The Lost Art of Letter Writing

Pen Pal Program FAQ



1………………………………………………………………………………………………………………………………………………………..…Review Program Information below. 


2……………………………………………………………Send your pen pal a letter using your assigned pen name and our virtual mailbox as your return address.


3………………………………………………………………………………………………………..Wait for a response letter that will arrive electronically to your email inbox.




Consider the following before you become a pen pal… 


a) Why do I want to write to someone in prison?

It’s important to take some time to ask yourself what you want to get out of a pen pal friendship. It is absolutely okay to not have a complete answer, but it is good to think about what your motivations are. We all carry lots of assumptions and need to continuously challenge them. Ask yourself what assumptions you might have about people who are imprisoned and how that might impact the way you write.


b) What is my capacity and commitment?

For many prisoners, receiving one or two letters from someone who promises to write regularly but then fails to follow-up can be incredibly disappointing. So please think about whether you can realistically commit to regular letter writing. Being a pen pal doesn’t have to be an intense time commitment; letters can be as long or as short as you want them to be, but we do ask you to write at least once per month. It’s also important to be upfront with your pen pal about how often you will write, so you don’t create false hope or unfulfilled promises.


c) How might I deal with hearing about the prison system?

Writing to people in prison can often lead to a deeper understanding of the physical and emotional hardship of imprisonment. Sometimes people inside share experiences of trauma that can be upsetting to hear about, so it’s good to be prepared for that possibility. You may want to think about what supports you have in place if things come up that are upsetting or triggering.


d) Am I anxious about writing to a prisoner and/or giving out my personal address?

Many of us feel nervous about sharing personal information with brand new people in our lives and that is quite reasonable. There is, however, extra stigma around sharing information with imprisoned people. It is important to be clear about our own boundaries while also reflecting on what assumptions may lay beneath any fears or worries we hold. We encourage everyone to do what feels right for themselves while at the same time looking deeper at what might reduce fear as we try to build connections and community across prison walls.  Inside Circle will protect your full legal name and will not disclose your home address as part of this program. 


e) What kind of difference does letter writing make?

Letter writing may seem like a small act, but it can have a big impact – for everyone involved. Not only do letters provide an important form of connection, but when prisoners receive mail, it is a message to prison staff and other prisoners that this person has support and is not forgotten. This can be a vital way to reduce violence against people who are locked up. Likewise, writing may have a big impact on you – it may change the way you think about prisoners, it may challenge assumptions you have, and you may learn important things about yourself in the process. Try to be open to the possibilities.

General things to keep in mind when writing…


Be conscious of trying to approach letter writing from a framework of solidarity rather than charity. The Inside Circle letter writing project is not about condescending notions of ‘helping’ prisoners, but rather about connecting with and supporting each other. The project is about building and strengthening community across prison walls.

Don’t pretend to know someone else’s situation if you don’t. Expressing things in this way will compromise effective communication and can create unfair power dynamics. That being said, this is an ongoing learning process for us all. If you want more information about navigating these issues (solidarity, support, privilege, etc.) get in touch with us directly.

It is generally impolite to ask people what they are in prison for. Imagine if someone asked you to describe the worst thing you’ve ever done and how that might make you feel. Check your assumptions about why you want to know the reason they are imprisoned. If your pen pal voluntarily discloses their conviction history (which many people do), that’s one thing, but requesting that information can come across as invasive and judgmental.

Likewise, if your pen pal has not voluntarily disclosed their conviction history, we ask you not to try to find out this information by other means. In our experience, knowing this information can create unhelpful barriers and judgments that impact trust building. 

Confidentiality: Please be respectful of privacy when it comes to sharing the content of letters with other people. It is great to talk generally about the project with others, but you should not disclose personal or detailed information with other people, unless you have permission to do so. Again, this is not only a privacy issue, but one of trust.

Prison Mailrooms


While we generally encourage outside pen pals to take their lead from their inside pen pal, it is also important to note that mail going into prisons is screened and read more frequently than mail coming out of prisons. Don’t assume that just because your pen pal disclosed personal information in their letter that it’s alright to discuss it freely from then on. If unsure, ask which topics they feel comfortable talking about, and whether it’s okay to reference information they revealed in previous letters.

If you want to send something to your pen pal beyond a simple letter (such as a photo, or magazine or newspaper clipping, stamps, etc.), you should ask what specific restrictions apply to the prison or detention facility where they are held.


Negotiating Your Own Safety


Always keep in mind that it is very possible that all incoming letters will be read and screened. Do not include any incriminating information about yourself, or the person you’re corresponding with. Prison Services have been known to share sensitive information with other arms of law enforcement. Be mindful not to disclose your immigration status or other information that might compromise your safety. If unsure, err on the side of caution. That being said, our intention is not that you be completely self-censoring; we understand this project as an experiential act, so if you and your pen pal have established what you are each comfortable discussing, we don’t discourage experiential discussion, just exercise caution.

You should also communicate your own needs in corresponding, and the specific information you do and do not want disclosed in letters. This might include your own history of imprisonment, parole conditions, or added surveillance you are under as a result of this, etc, that you think your inside pen pal should know. This way they can be better informed in terms of what they should and should not be communicating in their letter, in the interest of not compromising either of your safety.

Setting Boundaries


If you feel uncomfortable or that lines are crossed with your pen pal on any front, please don’t hesitate to seek the support you need. You can send us an email directly at [email protected] including PEN PAL in the subject line. 

If things don’t work out with your pen pal, or you decide you can no longer continue the correspondence for whatever reason, that is completely your decision, and we can match you up with someone else. Please just let us know so we can find them a new pen pal.

Some letters received may have a sexual or romantic tone. This can be in part because sex, gender, and sexual identities are things people in prison often have limited access to healthy representations/experience of and may want to talk about these issues. Being interested in and asking questions about your romantic life isn’t necessarily an indication of romantic interest in you, though it may be. In our introductory communication to prisoners, we explain that the Inside Circle pen pal project offers friendship and community and is not intended to facilitate romantic exchanges, legal services, financial support, business ventures or anything else beyond the realm of shared connection to the human condition. If you feel uncomfortable with any content/propositions, we encourage you to be upfront with your pen pal in setting boundaries, and expressing your intentions, in a firm but caring way.


Important Note about Matches


There are often significant differences between inside and outside pen pals, particularly with respect to personal experiences, levels of privilege, and areas of interest. So it is important to be aware that you may be matched with someone who is different from you in lots of ways. From our experience, this can be a positive thing, and most people (both inside and out) have made great connections through and across both similarities and differences. We hope that you will too.

Inside Circle is committed to supporting all prisoners, regardless of their charge or conviction. We take this approach because we recognize that the reasons why people end up in prison are complex and we are not in a position to judge. We also recognize that the prison system disproportionately targets people who already face high levels of inequality, discrimination and oppression.

This is not to excuse the serious harms that some prisoners may have committed; rather, it is to recognize that giving up on people or reducing them to their conviction is not a successful strategy for accountability and healing. Inside Circle is committed to anti-violence work and believes that such work requires us to break cycles of violence rather than perpetuate them through isolation and marginalization. 

Inside Circle feels it is important to respect all pen pals’ boundaries and comfort levels. At the same time, it is important to be aware that we do not ask prisoners to disclose what they are in prison for (just as we do not ask outside pen pals to tell us the worst thing they have ever done). We have no direct access to prisoners’ records, so we can never fully guarantee the background of the person you are matched with (just as we don’t/can’t guarantee the background of outside pen pals either).

Initial Contact


Writing your first letter can be exciting and daunting. If you aren’t sure what to write, start by saying something about yourself, your interests, and why you want to be a pen pal. Ask some questions about what your pen pal is interested in and what they’d like to get from the pen pal project. Don’t worry if it takes a bit of time to build up a relationship – as with any friendship, you’ll probably find you have lots to write about once you’ve got to know each other better.


Tips for your first letter:

  • Write your first letter on plain or lined paper, in a plain envelope (no stickers, no photos, etc.) to increase the chances of your first letter getting through.
  • Make sure you include the following on the envelope (or your letter will not go through):

      – Prisoner’s full name and prison number

      – Prison address and postal code

      – Return address using your assigned pen name and virtual mailbox address: 

Line 1: Your assigned pen name

Line 2: Inside Circle

Line 3: 2443 Fillmore St. #380-4123 

Line 4: San Francisco, CA  94115


  • You must correspond using your assigned pen name rather than your legal name. 
  • Make a copy of your first letter in case it doesn’t get through right away. There are many problems with mail going ‘astray’ and people getting transferred without notice.
  • Please confirm with us once you successfully get in touch with your pen pal. Just drop us a line either by email or post to say that you’ve written and when you’ve heard back from your pen pal using our [email protected] address and the subject PEN PAL.
  • If you don’t hear back from the person you’re corresponding with within 3 weeks, send them a follow-up letter.  Unfortunately many letters go “missing” in the prison system and so the person may not have received your first letter. Prisoners also have limited access to stamps and envelopes so they may not be able to respond right away. If you don’t hear back on the second letter, please let us know.

Pen Pal Checklist


  • First letter:  
    • Have you included your full pen name and return address (the Inside Circle virtual mailbox address) on the envelope? 
    • Have you included your pen pal’s full name, address and prison number?
    • Did you make a copy of your letter (or a note of the date you sent it) in case it doesn’t get through?
  • Please let us know when you’ve sent your first letter to your pen pal and drop us a line (email: [email protected] with the subject PEN PAL) when you hear back from your pen pal so we can confirm the match.
  • If your pen pal is moved or released, please let us know so we can update our records.
  • If you move or change your contact details, please let us know so we can update our records. We will use the email you provided upon sign up for all contact. 
  • If you decide you aren’t able to write to your pen pal anymore – for whatever reason  – please let us know so we can match them with someone else.
  • Be sensitive and careful about not putting the safety of your pen pal at risk. If in doubt, check in with us. If you run into any problems, have questions, or want to talk about issues that come up, please get in touch with us.