I’ve heard people say we found love in a hopeless place. While writing this article, it got me thinking; does one of these hopeless places include finding love in prison?

Well, there is a chance that you can find love with that person behind bars because you feel they’re still worth a chance. And knowing the pros and cons of dating an inmate, you feel I can still cope with it.

Inasmuch as there are many “negative” characters locked up in prison, there are some who have become better people and wouldn’t mind having a relationship with you on the outside.

Besides perseverance, transparency and good communication, there are other tips to consider before dating a prisoner.

Here are 12 tips that you must look out for before going into that relationship with a prisoner.

relationship with an inmate

This is a very important question you must first ask yourself before going through with dating an inmate.

Why do I want to date this person? Will I find luck dating a prisoner than a law abiding citizen? Are you restricted by certain factors that cannot guarantee that you’ll devote your time, energy, and emotions in a “normal” relationship?

Do you think dating an inmate will boost your confidence and self-esteem or you feel dating a prisoner will give no room for cheating?

Listing out your reasons is the first step to dating a prisoner. You must know what you want in such a relationship and if the prisoner has the desired qualities that compliments areas where you think you’re lacking. 

This will help you appreciate and respect each other more, plus provide you with the strength to go through with the challenges of dating a prisoner.

One way to really understand what you need to put into a prison relationship for it to work is talking to someone in the same situation as you are for advice and support.

Some of them may have gone way ahead of you, so you will need to ask them how it was possible to still pull through despite the difficulties of dating a prisoner.

You should understand that dating a prisoner involves little or no contact, so you won’t get to enjoy a hug from your partner after a hard day, you may not be able to talk over the phone often, you can’t get intimate benefits.

If you understand this, you’ll be able to prepare for the journey ahead.

Before committing yourself in a relationship with a prisoner, you must find out what crime brought the person there in the first place.

Although they must have been kept behind bars for a terrible offense, it doesn’t mean they haven’t changed for better. It only means you’d have to cope with the person’s offence which is already part of their history by the way.

Knowing the prisoner’s history will kind of give you a hint of what to look out for in future.

However they may still remain unrepentant and will have the tendency to exhibit traits of violence or assault.

A person that was convicted of robbery, illegal possession of drugs or weapons, or murder and still exhibits little traits of their past once in a while is a wrong choice for a relationship. Therefore, before committing yourself to a relationship with a prisoner, ask about the crime for which he/she was locked up, and find out if they’re already taking steps to improve on themselves.

Know when the person you intend to date is due to finish his/her jail term and reunite with you on the outside.

You may prefer to date a prisoner who’s weeks or months from getting out of prison, or best someone who has a bit of time left so as to get to know the person more. I suggest at least three months or more.

It is important to wait a little longer to know who you’re really involved with because it will give you a chance to solidify your relationship on the trust you’ve both built over time.

Be clear on your expectations from the relationship, let it be one that’s workable and realistic. You should know what you want from the relationship like: do you want a partner that can help you raise your kids?

You just need a companion? You wish to learn some values you think he/she possesses? Or are you in it for the money? If you’re clear on your expectations from the prisoner with whom you want to create a relationship, then you can go ahead.

However, the only way you’ll be sure of what to expect is by having that talk with them. Ask them what their plan for the future is, and if they share the same expectations from you.

If the one you intend to start a relationship with is constantly being locked up in segregation commonly called solitary confinement, then that’s a red flag. Note the word “constantly” because being locked up once or twice doesn’t mean such a person is unyielding to change as it might as well be a mix up or mistake.

Find out how frequently they’ve been locked up in segregation. For instance, if such a person was put in jail for drug possession and is constantly getting into trouble for the same crime in prison, you should know better whether such a person won’t go back to such crime once out of prison.

If they always claim it’s not their fault for going to segregation, you should also be on the lookout because such a person wouldn’t want to take responsibility for anything and will possibly make terrible decisions outside of the prison walls.

You shouldn’t just end up with one lazy ass, know more about what they do with most of their time. One thing I know is that some prisons offer a wide range of extracurricular activities for prisoners plus an option of even working to earn money.

If the person you’re involved with can’t make time to learn a skill, vocation or even enroll for a program, then it is very possible such a person won’t do anything when out.

Ask what the person does with his/her free time? What kind of skill he/she is learning? If he/she is considering furthering their education during their free time? And a lot of others.

However, if they spend most of their time in front of the TV or playing cards, still try to find out if they would be willing to do something more beneficial so you will at least have an idea of what the person is going to turn out to.

I know most prisons would not allow conjugal visits, so how do you know if you’re sexually compatible with such a person? One way I recommend is through phone conversations and letters.

Are they more open to erotic messages? Do they shy away from topics relating to sex? Are they too explicit? Are they obsessed by sex? These are things you should know and can find out through phone calls, letters, or in a one on one conversation with them.

In absence of conjugal visits, you can still find out if you two are sexually compatible with these mediums.

Find out who comes to visit them to know if it’s mainly just family or visits from “women friends.” You should endeavour to know if the person you’re going for loves and cherishes you just the same way you do to them, or they’re just in for a ride. Who knows, you might be in a competition with others.

Ask them for their visitors list and examine how many are labelled “family” or otherwise.

I’ve seen prisoners who don’t get calls, letters or visits from family members due to reasons which I know are not far from negative. Therefore, it is important to inquire if they’re in contact with their family, how often they communicate, if they’re on talking terms at all. 

If their relationship with their family is estranged, you should inquire about the cause of it. Is it because they stole from their family, or it’s because of some kind of altercation? Inquire about these things.

Prisoners who communicate more with family members will definitely have a stable relationship with their family members and so, are more likely to possess a positive attitude and become better people. You can even get to meet them when your partner is out of prison.

It is difficult to know if you’re being played by the person you intend to start a relationship with in prison. Ask yourself, Is this person truly who they make you believe to be?

Are they faking their fashion style? While in prison, I came across people who complained how their prison clothes were demeaning and poor quality that if they were out there they wouldn’t put on clothes of such poor quality.

Do they maintain healthy hygiene? Some folks in here will only shave or clean up when they’ve visitors.

Find out if they’re as smart as they claim to be. You can try by starting a conversation with them in their areas of interest and try to determine if the person is educated, intelligent, eloquent with words, or is just trying to paint themselves in the impression of which they’re not.

Try to find out what they’re committed to do, what plans do they have for the future when they’re out of prison.

Start up conversations in those areas to know if such a person still has dreams and is planning towards achieving a better future not only for himself, but for the both of you.

Love can still be found in hopeless situations, one of which is in prison. Dating a prisoner is possible if you follow through with the tips I listed in this article.

Note that it’s not that easy and is not going to be all rosy as there will definitely be challenges. As such, I wish you goodluck!

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