Reentry Lifeskills

February 2, 2023

How to Write a Letter to an Inmate or Prisoner in Jail?

Writing a letter to someone in prison can be a difficult task. It’s important to remember that incarcerated individuals often feel isolated and forgotten by their friends and family. Writing a letter provides emotional support, letting the individual know that someone cares about them.

Here are some tips to consider when writing a letter to someone in prison:

  • Address the letter formally. Start by using the incarcerated individual’s full name, followed by their prison ID number and address. Ensure all the information is correct so the letter will be delivered to the right address.
  • Keep the content of your letter positive and respectful. Avoid discussing topics related to their crime or any negative issues that could cause them to become upset. Instead, try to focus on topics that will make them feel supported and encouraged, such as their hobbies or interests.
  • Include personal stories and anecdotes. Talk about things that are going on in your life or stories that might interest them.
  • Keep the conversation light and upbeat. Avoid discussing serious topics or anything that could be seen as confrontational.
  • End the letter with a positive note. Finish by expressing your hope that they remain positive and hopeful about the future. Let them know you’re thinking of them and wishing them well.


Writing to someone in prison can be a difficult task, but it can also be extremely rewarding. It shows that you care and are willing to provide emotional support to someone in a difficult situation. Keep these tips in mind when writing your letter. It can be an uplifting experience for both of you.

Conversation Topics That Work Well When Writing a Letter to Someone in Prison


When you sit down with a blank sheet of paper and a pen, it can take time to come up with ideas for topics to discuss in your letter. Here are some conversation topics that work well when writing to someone in prison:

  • Talk about memories from before they were incarcerated. This can help them feel connected with their past and the life they used to lead.
  • Discuss current events that are happening in their area or around the world. Keeping up with the news can help them stay informed and engaged with the world while they’re in prison.
  • Talk about hobbies or interests that you may have in common. This can help them feel connected to the outside world and give them something to look forward to when they’re released.
  • Focus on the future. Talk about their plans after they’re released and how they can work toward achieving their goals.
  • Share funny stories and anecdotes. This can provide much-needed comic relief and help them stay positive in a difficult situation.


Writing to someone in prison can be both a difficult and rewarding experience. Remember to keep your content positive, respectful, and uplifting. The topics you choose can make all the difference in providing emotional support and helping them stay connected to the outside world.

Example Letter To an Incarcerated Individual


Dear (First Name),

I hope this letter finds you doing well and in good spirits. I wanted to write to let you know that I’m thinking of you and wishing you the best.
I wanted to share some news about what’s been going on in my life recently. I’ve been working on a project for the past few months, and it’s finally ready to launch! I’m so excited to see the results.

I also wanted to catch up on your hobbies and interests. How have you been passing the time in prison? What sorts of activities do you enjoy?

I hope that your days are filled with positive energy and that you’re using this time to build skills for your future. I’m sure you have a lot of dreams and goals, and I’m confident you’ll achieve them.

Take care,
(Your Name)

This is a highly simplified yet good starting point for writing a letter to someone in prison. Be sure to use your own words and personalize the content as much as possible to make it meaningful for the recipient.

What Does Reentry Lifeskills Offer?


Reentry Lifeskills offers a comprehensive range of education and assistance to people looking to lead more fulfilled lives. Courses are designed for everyone, from those recently released from prison to individuals with complex struggles in their lives. The course content is unique in that it is based upon real people’s stories of how they overcame difficult obstacles and challenges, providing practical wisdom and insight into successful reentry into life and society. Participants learn basic skills such as goal setting, problem-solving, communication, and developing trust through these stories. With the development of these skills and more, Reentry Lifeskills works to empower its students with the knowledge needed for making all-important lifestyle choices that can lead to increased happiness, productivity, self-reliance, and personal growth.

Incarcerated Individuals Are People Who Matter


Language is powerful, and it’s important to use the right words when discussing incarcerated individuals. Referring to someone as an “inmate” stigmatizes them in a negative way, connotating a loss of autonomy. Moreover, terms such as “prisoner” suggest an attitude of us versus them that doesn’t acknowledge the person’s individual humanity or basic rights. By using more respectful language, like “incarcerated individual,” we can emphasize their individuality and, at the same time, create an atmosphere of compassion and respect, which can lead to better outcomes for individuals leaving prison or jail. Ultimately, by choosing to refer to incarcerated individuals with language that communicates understanding and compassion, we strive towards reducing long-term disparities that feed into mass incarceration and its accompanying cycle of poverty.

Contact Reentry Lifeskills Today


At Reentry Lifeskills, we understand that everyone has the potential to turn their lives around and live productive, fulfilling lives. We offer a range of courses that can help incarcerated individuals make meaningful changes in their lives, build self-confidence and make a successful reentry into life and society. Contact us today to learn more about how we can help you or someone you care about. Let’s work together to build a better future for us all.

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