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Dating an Inmate

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Growing up, most girls imagine themselves as a princess marrying their Pince Charming. Sometimes, that illusion fades away as they realize that their Prince Charming is behind bars. In fact, it's surprisingly common for women to intentionally start dating an inmate.

My daughter's father was in prison for years. I know other people that faithfully served prison sentences with their boyfriends. I've heard the stories from both of them, and have learned quite a few things myself. From gifts bought from behind bars to inmates scamming as many girls as they can, whatever you've heard could be true. That's why it's important to learn about prison dating before picking up a pen to write a letter.

Prison Dating Sites

When people decide that they want to date an inmate, they often think of the many benefits. Your newfound love will always call, be nice and you can decide how involved they are in your life. However, most people are left wondering where to begin in this entire process. The secret is that there are prison dating sites. However, they are technically called prison pen pal sites.

These websites show you the inmates that you can write to so that you can be pen pals with someone. That is a great way to start if you're considering dating an inmate.

Start as Prison Pen Pals

It can be tempting to jump right into prison visits, but it's important to take things slow when it comes to prison relationships. Most of the people in federal prisons have plenty of time of their hands, so they might get impatient. Make sure that you set boundaries as you would in any other relationship, and then stick to them.

In the beginning, before phone calls and visits, make sure that you start out as pen pals. This is similar to how you would want to text someone for a bit before meeting in person if you met a person on an online dating app.

After you take your time getting to know them, you can then enjoy phone calls and in-person visits or video chats.


What Do You Write to Someone in Prison?

When you first start writing a prison inmate, it can feel a bit awkward, especially if you've never had a prison pen pal before. Don't tell them too much personal information, such as your full name or address, until you know that you will be safe. You also want to follow basic internet safety rules, such as not telling people your social security number.

Aside from those rules, there are plenty of things to talk about. Being a prison inmate is akin to living in a fish bowl. They are looking at the world through a very small lens, so they'll love to hear you talk about pretty much everything. Take this opportunity to get to know each other, too. Here are some great topic ideas:

  • World events
  • News stories
  • Celebrity gossip if they have favorite stars or artists
  • Ask questions if you're curious about prison culture
  • Let them know if you are, or are not, okay with having an inmate boyfriend
  • Tell them about yourself, such as hobbies, interests, etc.
  • Ask common getting to know you questions

As you continue to write each other back and forth, you'll find that the conversation flows more naturally.

Falling in Love With a Prisoner

It can sound crazy to fall in love with letters or emails, or even just phone calls, but it does happen. It happens more than most people care to admit. If this happens, it's important to decide whether you're okay with your Prince Charming being behind bars.

If you do, be prepared. Learn about dating an inmate, and what that can mean for you. Read tips on inmate dating. There's nothing wrong with dating an inmate, but it's important not to have illusions about it.

How to Make an Inmate Fall in Love With You

If you've already started to fall head over heels for your inmate, it can be disheartening to know that he doesn't feel the same way. Give him some time, and follow these tips.

Open Up

It's normal for people to have a strange curiosity about inmates if that's a new world to them. However, it can also lead to inmates having feelings for someone that doesn't have feelings for them. This is particularly common through pen pals.

Not only will opening up let him know that you're not doing that to him, but it will also give him the chance to get to know the real you. People don't fall in love until they get to know the real person.

Be Understanding

It's important to be understanding if you're in a relationship with a guy in prison. He can only call at certain times, and he doesn't get to send you gifts. It can be hard for him, but you can show him that the things that matter the most don't cost money. Be understanding of his limitations and make sure you have the phone next to him.

Ignore Regular Dating Games

We've all heard of the classic rules that you should wait to text someone back or not answer the phone for a few days. This is not a good idea when it comes to dating a man in prison. He'll think you're ghosting him or get irritated. Instead, cut out the games and just relax.

Show Him You're Thinking About Him

Although he's in prison, you can still show him that you care. Join a prison forum to learn more about what his life is like, and let him know what you learn. Take the time to write him an email every night before you go to bed. Pop up for a surprise visit if you can. Send him a book or two. Although you shouldn't send him money constantly, there's no harm in a little care package that shows you were thinking of him. (TIP: Make sure that you don't constantly send him money or gifts to make sure that he is not using you.)


Signs an Inmate Is Using You

Although there are plenty of situations that are genuine love in prison, there are also plenty of men that get a pen pal in hopes of having conjugal visits and some new blankets. The culture of prison is drastically different than the outside. Some guys have it rough. They don't have family or a friend in prison to help them out, so it doesn't take them long to start using people. Watch for these signs an inmate is using you.

Start Off Small and Working Their Way Up

Not all inmates take advantage of people that they talk to. However, the ones that do can be very good at what they do. They can write for several months without asking for a single thing to make it look like they don't want anything from you. Then, they will slowly ask for things, slowly working towards larger amounts. If they think you're head over heels in love with them, they'll flip out when you start telling them no. That's an important pattern to watch out for.

Crazy Stories

Inmates that are full of crazy stories as to why they need money are just like the scammers that you'll come across in real life. If you wouldn't fall for it on an online dating site, don't do it with an inmate.

You Met Him Online

It's important to note that there are plenty of inmates online that won't scam you. However, they are more likely to scam you than if you meet an inmate through a mutual friend.

Asking You to do Illegal Things

A man that loves you won't put you at risk. It's that simple. If he's asking you to take drugs or other things into a prison that could land you in prison, it's not love.

Signs an Inmate Is in Love With You

There is a common misconception that men and women in prison are horrible, and they are just using people they connect with on the outside. While this does happen, there are also situations in which a prisoner and pen pal do genuinely fall in love. Watch for these signs an inmate is in love with you.

They Remember the Little Things

When a person is genuinely interested in getting to know you, they tend to remember certain things about you, like your favorite color or favorite food. They might remember your routine and what you like to do in your free time.

Making Efforts to Change

He may have been doing his time before, but now he suddenly has a purpose. He starts enrolling in programs and taking classes on communication to be a better person. The fact that he's suddenly trying to be a better person that won't wind up back in prison now that he's in love with you is a good sign.

You'll Feel Loved

When a person loves you, they make sure that you feel loved. Granted, the two of you might not be able to go on romantic dates or take a vacation, but that doesn't mean that the feelings are different. The situation is different. The location is different. There are plenty of things that are different when you're dating an inmate, but there are quite a few things that are the same too. If you feel that he loves you, there's a good chance that he does.

There's Communication

When one person loves another, they take responsibility for their actions. They take the time to work through problems. Regardless of where your partner lives, you'll find that they do this when they love you because they want to make it work.

He Sends You Gifts

Some men won't be able to do this, but if he can and does, it's a sign that he's not just using you. He'll draw or make you something. Some men find a way to send you flowers, or they will send you a card. It's a sign that he's thinking of you.

When dating an inmate, it's important to take things slowly. Write letters for months before visiting. Set boundaries on how much you will do for him before you catch feelings, and make sure that you don't send him money for several months, if ever. Don't let him take advantage of you. More than anything, be prepared for the heartbreak that not being able to call him and see him when you want will inevitably cause. Don't fill your own head with empty illusions about what prison love will be like.

This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.

© 2022 Amber Lynn