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10 Tips to Dating a Prisoner

dating an inmate tyro blog

Dating and prison are words that do not seem to go together.

Prison is not typically a place we think of when we imagine a date.  And yet, many women find themselves “dating” men who are in prison.

There are a lot of things to consider before you should commit to dating someone who is in prison.  So, before I share some tips on dating someone in prison, I am going to spend a little time blogging about how to decide if this is the right decision for your life.

Finding your prince charming

No little girl ever imagines her prince charming as a man who is in prison.  We imagine a man who is strong, honorable, kind, brave, courageous, loving, and gentle who adores us.  Unfortunately, sometimes, that man is in prison.

I know many men who have transformed their lives and are amazing men of honor who are still in prison.  I also know many men who are in prison who have NOT transformed their lives who prey on women so they have someone on the outside to provide money, material things, and a connection to the outside world. So how do you know who this man is that your friend is trying to set you up with?

Me and my husband with our baby daughter

Keep in mind that loving a man who is in prison is full of heartache.

 You cannot spend time together whenever you want to.  You do not get to see how he interacts with his friends and family, nor how he acts with your friends.  Prison visiting rooms, phone calls, and letters will be the way you communicate and date.  You will never, ever, ever be alone until he comes home.

My most important advice here:  If you know you do not want to spend the rest of your life with this man, do not date him.  Do not waste your time, and his.  If, however, you think this man could possibly be someone you could imagine spending the rest of your life with, take the time to get to know him better.  Write letters, ask a lot of questions, check out his answers to be sure he is who he says he is BEFORE you start visiting him.

Handpicked Related Content: Married to an Inmate

I am married to an inmate. Wow.  I kept saying that in my head over and over again.  I am married to a convict!  How in the world did this happen?  I never imagined that I would marry a man who was in prison.  I was in shock that my husband was in prison.

Read more

husband in prison ron and cathy tijerina

Note: The women I know who have dated men in prison and it has worked out really well have all been Christians who have prayed and sought wisdom from the Lord before agreeing to make a relationship romantic with someone in prison.  I personally believe this is the best way to make any decision about dating anyone.


If you have decided to go ahead and date someone who is in prison, it is really important to set some boundaries and stick to them.  Remember that prison culture is completely different than our world out here.  There will be some strange rules and also a strange curiosity you may experience that drives you to find out more about the world of prison.  Establish your interest in the man; not just the culture of prison nor the safety of dating someone who doesn’t have much access to other women.  Sometimes, that seems safer than dating someone on the outside.  This is especially true for you if you have been hurt by someone who found another woman.

If you are still sure—here are some tips to dating someone who is in prison:

  1. Write a lot of letters to get to know him. If he doesn’t write back, do not continue the relationship.
  2. Do NOT send him any money or purchase food/sundry boxes for him. Tell him you are not going to spend any money on him except for collect calls and eventually visits. This important boundary will avoid being taken advantage of.  Wait at least 6 months before you spend any money on him.  If he loses interest, he wasn’t really interested in YOU – just in what he could get from you.
  3. Do not take your children to a prison visit unless/until you are engaged. Then, let them decide if they WANT to meet him in person.  A phone call may be enough.
  4. The first couple of months, write letters more than you plan visits. After several months of getting to know him via letters, schedule visits.
  5. Once you are visiting, plan a surprise visit or two. You will learn a lot about his temperament by surprising him with a visit.
  6. Do not kiss him until you have been visiting him for at least 6 months. This may seem like a long time out here—but remember that you will only have very limited time together during those six months. Don’t rush into kissing because it can cloud your judgement and you need that time to really get to know him.
  7. After you decide you are officially dating, take your best friend with you to visit him. Her opinion is important AND it is good to see how he interacts with your friend.  Plus, if it goes well, you will have extra support.
  8. Spend a lot of time sharing your dreams and goals and find out what his dreams are. Can you both achieve your goals if you continue in this relationship? If yes, keep going.
  9. If you both decide this relationship is getting serious, get involved with support groups and courses that teach healthy relationship skills. Hopefully, there is a class you can take together with him (or each of you take and talk about together)
  10. If you have children living with you, do not live with him for at least one year after his release. This will give both of you time to get to know each other on the outside.

I am rooting for you-


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  • Chelsea
    Posted July 16, 2019 at 10:15 am

    I’ve known the man I’m “seeing” for about 7 years now. We were friends before he went in… we lost touch when he went in and recently started writing letters back and forth and started with the phone calls… I see a future with this man, he’s never once asked me for money, nor anything of the sort. Do these guidelines still apply?

    • Catherine Tijerina
      Posted July 18, 2019 at 10:05 pm

      Hi Chelsea-
      These guidelines will help you keep your relationship in the healthy zone. As you transition from friends to a romantic relationship. Check out some of my other blogs on how to “date” in a prison visiting room and grow your relationship if you are planning to get married. We built some great memories and a solid foundation for our marriage while Ron was in prison. It was so worth the effort to create a thriving marriage 🙂
      I am rooting for you!

  • Jacqueline
    Posted September 23, 2020 at 2:28 pm

    i loved your post.

  • victoriea
    Posted September 6, 2021 at 8:57 pm

    When I was twenty-six years old I started talking to this inmate from prison for prostitution when he was 15 and we build a bond. My family eventually found out, I stress and broke it off. It’s been four to five years yesterday he called me. Turns out he has been trying to connect back with me. I decided to give it a chance and he sounds so sincere but I don’t know. Apart of me thinks it’s possible but I don’t want to get hurt, in danger or hurt my family and get them in danger. I have never been in a relationship and the first man I had a bond with a connection is a Pimp . He working on getting his life together by going to school and getting out in 2 to 3 months. What should I do.

    • Catherine Tijerina
      Posted September 13, 2021 at 6:52 pm

      Hi Victoria-
      Any relationship involves risk. Being in a relationship with a prisoner or someone who just got out of prison has even more risk involved. Most prisoners return home with at least some PTSD and social anxiety. It takes some time to work through feelings of being overwhelmed and adjust to the pace of life on the outside. Having said that, if you care about him I think you should find out if there is a possibility for a long term relationship with him. Be cautious, take it very slowly and follow your gut. Don’t leap into an intimate relationship. Be friends, date, and navigate through his Reentry. Then, make a decision about a romantic relationship. I am rooting for you!

  • Elizabeth
    Posted December 2, 2021 at 1:15 pm

    I started a friendship without someone on the outside and we grew to connect with each other, I found myself getting attached and there was no real clarity. I expressed that to him and decided that I needed to be in a better mental space before I started to get serious especially because there was intimacy involved I simply just didn’t want to cloud my judgement. Several months later after I had cut ties with him I received a message on FB from his sister whom I’d never met stating that he was actually wanting to reconnect with me, I gave it some time, looked him up and finally reached out and began writing to him. I care about him, but I also know there are so many things that he needs to heal from, and honestly I know that its going to take time. Trying to navigate the idea of entertaining him, and possibly investing time and energy with him. It can be scary, but so can any relationship!

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