Dating Someone In Jail (13 Fab Ways To Make It Last)

Are you dating someone who is in jail? Do they allow conjugal visits? Have you met someone who was incarcerated when you first were introduced to them? 

It’s really tough to keep a relationship going when one of you is in prison. You may feel lost and confused right now, not knowing how to best get to know each other in this situation.

Have no fear; we are here to help you with some fabulous ways to make it work. In this article, we’ll look at all the details that come with dating someone in prison and how you can make it work. This is important information to know if you are dating a prisoner and are about to fall in love with this person. 

You may not know this, but in the United States, there are more than 2.1 million men and women who are behind bars! That’s a huge number!

I get it; you just want him to come home! Unfortunately, I can’t make that happen, but I can give you tips to follow if you’re ready to take this relationship to the next level. Are you ready to learn more? Let’s get started!

Top Ways to Make It Last with Someone in Prison

1. Write letters

If you have not met him yet, be sure to send him plenty of mail. Wait for him to reciprocate before you spend too much time doing this. Talk about who you are; what do you do for a living? Why did you decide to start writing to him? What do you like to do for fun? Explain what your life is like so that he can know what it’d be like to be with you.

Take your time writing to him. You don’t need to rush things. Falling in love with someone via letters is an easy thing to do, so watch your feelings closely. You don’t want to fall head over heels for a person who is talking to multiple women or doesn’t feel the same way about you. Make sure he writes you back, too. 

The relationship certainly shouldn’t be one-sided. There should be some give and take. He should be sharing what his life was like before prison, what he used to love doing for fun, and what he currently does for fun. Learn all about him to see if he could be a positive aspect of your life.

2. Find out why he’s locked up

It may be an awkward thing to ask, but you should definitely know why he’s in prison. Was it just one small offense, or did he do multiple things to get himself locked up? How bad was the crime he committed? Is he innocent? Get all of the facts before you fall head over heels in love with him, thinking he is Prince Charming with a bad rep.

3. Get to know him well

Again, before you invest too much in this relationship, you should learn all about him. What was his life like before he went to prison? How long has he been in there? What is his day-to-day life like now? Are there things that he’s going through that you can relate to? For example, if he has someone picking on him, you may have the same.

4. Find out if you have common interests

find out if you have common interest

The next thing you should do is to find out what the two of you have in common. Most inmates are allowed to play games like chess or watch regular television all day. Maybe his favorite show is the same as yours, or perhaps you both love playing chess. Discover what interests you have in common. 

To discover his interests, you’ll need to communicate often. Most inmates are allowed phone calls, so that is the perfect opportunity for you to get to know him better. Make an effort to give him a phone call as often as you can without seeming desperate. This will give your relationship a chance to blossom as you get acquainted with one another.

5. Don’t rush the relationship

One thing you know you have if you are dating a person in prison is time. They probably have months if not years left on their sentence, so you have plenty of time to build the relationship in a healthy way. There’s no reason to rush things and say, “I love you” too soon, even if you do feel that way. Instead, let everything take its course.

6. Decide together if you will be exclusive

Hopefully, if you are investing time and money in your visits to the prison for this guy, the two of you have decided to be exclusive, but you should talk about this topic together. Make sure you are on the same page, have the same feelings on the subject, and agree with the way you want your relationship to be.

This is especially important for you since you are on the outside. You have the chance to date whoever you want, really. So, if he is talking to other girls or getting visits from multiple women in prison, you know he isn’t serious about only seeing you, so don’t bother fending off other gentlemen. You can date around if he is.

7. Send care packages

For someone stuck in prison, nothing brightens their day more than a mail call. If they get an awesome care package from you, you can bet you’ll steal his heart in no time. 

Make sure you check with the prison to see what their rules are regarding what is allowed and not allowed as part of a care package. You might fill it up with books and letters.

Give him things to do while he’s locked up in prison. If you can, send him a deck of cards or some really cool stationery and pencils so that he can write you back. It never hurts to contribute to his commissary account, too. However, I would caution you about this until the two of you have decided to be serious with one another.

8. Find out if other girls are visiting him

find out if other girls are visiting him

Before sending him care packages, which take up your time and money, be sure you find out who is visiting him. Is he flirting with other girls? Does he have another girlfriend? You may be able to tell the truth by checking out the visitor’s log if the guards allow that. Confront him about who is visiting him in prison before committing to him.

9. Visit often

Each prison is different in its rules for how often they allow visitors. Find out what the policy is at the prison where he is locked up. If you can swing it, try to visit often. Your visits are probably the highlight of his week and mean the world to him. Plus, what better way to get acquainted than to talk to each other all the time?

10. Talk about important things

When you do talk, explain that you want to know about the important things in life. For example, ask him about his hopes, dreams, and aspirations when he gets out of prison. Hopefully, he will want to know the same things about you. Opening up about topics like this can really build a close and healthy relationship, a lasting bond.

11. Get to know his friends and family

If you have gotten serious with an inmate, he will probably have you meet his other visitors. This way, you can all get acquainted. Plus, your visiting times will eventually clash more than likely, so you’ll run into them sooner or later. You can then get better acquainted with them outside of the prison walls to learn more about them.

12. When you are ready, let him meet your friends and family

when you are ready let him meet your friends and family

If you feel the relationship is serious enough, you may want to bring your friends and family members with you to your prison visits. Let them get to know him so that they can see what he’s like. Plus, you’ve probably been talking about him non-stop; now, they can know who the heck you are gushing about and why you are crazy about him.

13. If he’s innocent, make calls and write letters on his behalf

If you are sure that your incarcerated boyfriend was falsely imprisoned, you can make calls to lawyers and judges possibly to see what you can do to get his sentence reduced. It may mean writing letters to your government or joining the Innocence Project, which works to help falsely accused inmates get out of prison.

You may want to lobby on his behalf to try to get him out of prison sooner. I’m sure you are dying to see him outside of those walls, so put forth the effort you can to get his sentence reduced if possible. It never hurts to try to do something like that. You may just be able to make a huge difference on his behalf! You just never know until you try!


How do you date someone in jail?

The best thing you can do is to communicate well with this person. He probably gets lonely in prison and wants to hear what’s going on outside the walls of where he is. He’d probably also like to get to know you better, so send lots of mail.

How do you tell if an inmate really loves you?

He doesn’t accept visitors from other women; he stops communicating with pen pals he had before you came along if they were also women. You know he only has eyes for you if he rejects advances from other women. You’ll also know he isn’t cheating on you!

How do you maintain a relationship with someone in jail?

Treat him like a pen pal and send him lots of letters; visit as often as you can so that he knows you care and want to make him a priority in your life. If you are in a relationship with someone in prison, you want to keep communicating.

Can my boyfriend cheat on me in jail?

I would consider it is cheating if he gets visits from other women. I’m fairly sure that prisoners can deny visitors, so even if he’s lonely, he could reject other women from seeing him. If he only has eyes for you, I would think he’d only want to see you.

How do you tell if a prisoner is using you?

Does he write to you and call you back? If you make an effort to do lots of letter writing but get no letters back, he is acting selfishly. You know he has the time to write you a letter or two while he is just living life in prison.

To Conclude

Are you dating someone incarcerated? What tips do you have for our readers that are in the same boat as you? How have you made your relationship work? We’d love to hear from you. Please leave a comment, and share this post with others who could benefit from it!

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