Skip to content Skip to footer

5 More Tips for Dating a Prisoner

Five effective ways to connect to a loved one in prison.

Keeping a relationship alive in the midst of a prison sentence can be a challenge. But you are not the only one who has gone through it. You might be surprised to know how many couples have made it through the others side of a prison sentence,  stronger than ever. Relationships in prison are going to require effort, but these tips can serve as a reference to make a prison relationship work

1. Get Ready to Write:

We talk about writing letters to inmates often. That’s because writing and receiving letters are the bloodline of any prison inmates relationship. This is a crucial aspect to dating someone in prison. Writing letters is  the easiest and most common way to maintain a good level of communication with someone who is incarcerated.

2. Make Communication Meaningful

There are a great deal of things we may want to talk about when we have the chance to talk to our loved one. However, with limited time to communicate with someone in prison, we have to make sure we prioritize the meaningful conversations first. This can include important life updates, plans for the future, family events, etc.

3. Stay Involved with their Family

This tip is typically more applicable if you have already been in a relationship with the prisoner prior to incarceration. Even if not, this is still important to read. Thus, staying involved with the family can be beneficial to all involved. By showing their family you still want to be part of their life, you show your loved one that their family still matters to you. This further helps you by still feeling connected to your loved one.

4. Keep Realistic Expectations

Make sure to do your research on prison relationships. One of the hardest parts of a prison relationship is adjusting to the difficulties of it. Be real with yourself. Be mindful of the struggle your loved one is in and don’t put added stress in their life or your own.

5. Ignore Doubters

There is a stigma that a prison relationship simply cannot work. You will cross paths with many people with this mindset, some that are strangers and some that you are close with. You must ignore these kind of people. Nobody but you and your loved one can determine if your relationship will work. TYRO is living proof that prison relationships can work. Do not let others affect how your prison relationship goes.

No matter the challenge, no matter the doubt, prison relationships can work. We at TYRO are cheering you on, you got this!


  • Sara
    Posted March 21, 2022 at 5:29 pm

    I really appreciate these tips you give, it really opens a persons eyes to the reality of the situation. My boyfriend and I were kids when we met, and hung out. And I have contacted him over the years to see him here and there. But we never got to actually spend time together in a manner of a relationship. We just wanted to be around each other, we were like best friends. In 2008 he was unfortunately sentenced to prison. He didn’t have any help or a lawyer and was sentenced to 17 year flat bid. He has already done 15 years. Talk about fate his cousin moved into an apartment close to my house and I was able to get his information and start writing to him. That started in 2012 and is still going strong, we were friends first, and he has always been very patient and kind. He offered to talk to my son as a friend when my son was having issues with (not having a dad around, my boyfriend is not the biological father) other kids in his school and our neighborhood. He has really been a great influence on my son and in my life. And we are thankful to each other because we have both grown so much. Your article gives me ideas to talk about that we haven’t so thank you.

    • Catherine+Tijerina
      Posted March 22, 2022 at 11:53 am

      Hi Sara!
      Thanks for sharing your journey with me. I am glad this blog was helpful. We are here if you have any questions or need support as he transitions out of prison.
      Enjoy the moments along your journey!
      I am rooting for you –

Comments are closed.