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Dating a man in prison is serious business. Why would anyone consider it in the first place is the question? Better yet, I think people really want to know how to find a good man in jail.

Well, there are a lot of women and men, too, who would rather date someone in prison than to be alone. However, I find that to be ironic as you-know-what because you’re still very much alone.

You spend your time on a free prison dating site looking for someone to love. When you find him, you’ll spend your weekends and holidays… alone. Your birthday will come and go and you will have spent it alone unless of course, it landed on visiting day.

Goodness, if all you want is a voice on the other end and some empty promises, there are plenty of single and free men who will happily fill the slot.

I can understand dating a man in prison if you are already involved when your man commits a crime. However, to actively search and find someone in prison says a lot about the person who does this.

Women are Drawn to Inmate Online Dating

You may not believe this but prison romances happen every day. Honey, there are all kinds of women wanting to marry a man behind bars and it’s not just women from the hood.

Some criminals marry their lawyers, while others become involved with their physicians and psychiatrists.

While watching the television series, Prison Break on Hulu, I understand how it happens but only after finding out one dude was in prison because of a baseball card!  It was a $300,000 baseball card, but how unlucky can you get? Did he deserve to go to a federal penitentiary? I think not.

He’s more of a criminal after being in prison than he was before he entered the correctional facility. And how about Lincoln Burrows? He was totally set up by some vicious elements in the political system. [Makes me wonder about president number 45, and his connections.]

When you think about Linc’s brother, Michael Scofield, who committed a bank robbery just so he could save his brother from frying on death row, I can understand dating a man in prison, but that’s television.

Jeremy Meeks with black hat and scarf thick designer sweater
Jeremy Meeks doesn’t really like the nickname, “Hot Felon.”

Well, wait. What about “Hot Felon,” Jeremy Meeks? He was convicted of possession of a firearm and grand theft in 2014. His mug shot ended up on Facebook and received over 20,000 likes then.

Meeks was released from prison in 2016, got a modeling contract and is now engaged to a billionaire’s daughter. So, this story may not be on television… yet, but this success story doesn’t happen every day.

Men in prison have no problems finding other female prisoners looking for love or women on the outside. It starts off innocent enough, I suppose, with emails. Then, one day, they make the ultimate connection in person.

Women like Phaedra Parks and Sheree Whitfield of “The Real Housewives of Atlanta,” know first hand what’s it’s like. Phaedra is an attorney who married Apollo Nida, another cutie pie, “straight outta prison.” Sadly, he’s in prison for the second time, but fraud is a non-violent crime. 

Sheree Whitfield says her honey, Tyrone Gilliams, is a long time friend who, by the way, “gets her.” She says he broke off the relationship because Gilliams didn’t want to get Whitfield involved in any unlawful activity. With that said, she knew something was going on. 

She assures her fans she did not know, but they all look at her sideways. Have you seen her house? Yeah, pretty darn elaborate if you ask me. The fact her man got caught and is doing time for a $5 million wire fraud scam could explain how she really affords it. [Rot in jail, Gilliams]

Personally, I can’t stand a man who robs from another. The rumor is they got married. Nevertheless, she was recently fired from RHOA because she doesn’t have a storyline. She can’t perform her duties as an Atlanta housewife as they can’t film in or near the prison.  

Read More: Did Shereé Whitfield’s Prison Bae Cause Her to Get Fired From the RHOA?

Well, twirling witch, Kenya Moore’s job wasn’t taken from her when she didn’t have a man – when she had to buy a man but I guess she always stirred the tea so her job was safe and secure. Okay, sorry back to Sheree… 

Sheree was married before to Bob Whitfield, a former Atlanta Falcons football player. Their history was shaky, some say abusive. So are these women looking for love or do they have low self-esteem?

It’s no secret prison brides have a chronicle of abusive relationships. Some women are oddly attracted to violent men?! However, they date these men while behind bars to protect themselves. I’m not sure I get it, but okay.

Be Careful Dating a Man in Prison

Surprisingly, if you’re looking for an inmate dating service, there are a few to choose from. The service matches male inmates with women on the outside they could be compatible with.

There are certain risks, although this is likely exciting for the females who want to date a “dangerous” man.

Maybe the woman gets off knowing that he is dependent on her. The inmates may not be all bad, as we know a lot of Black men are in jail or prison for no reason or little reason at all. Most are good men, fun, passionate, intelligent and you know, ripped!

While the two of you could have loads to talk about, he may not be totally honest with you about the details of his conviction. For that, you could find someone in prison by using the Free Inmate Locator.

I am all for writing to these men or becoming email pen pals but I don’t know if getting serious will work out for many women. There are over two million convicts serving prison sentences.

Although some men are locked up due to trumped-up charges, more are in US prisons for hideous crimes; rape, murder, and theft. You should not forget that.

Men are extremely more likely to be incarcerated than women. It only makes sense they want to find a mate before leaving prison.

I took to looking at some of the websites to see how to write someone in jail. The first site was WriteAPrisoner and I found one man matching criteria I set for myself. He sounds like a nice man and he likes to write poetry, so that piqued my interest.

Then I moved on to browse InmatePassions [an ex-convict dating site] and they seem to be a cool dating service to network and meet friends or lovers. The last one I checked out was Meet-an-Inmate. They claim to be rated number one pen pal site for inmates.

It’s free to send a letter to the inmates, however, the inmates must pay a fee to be listed on the site to receive emails. Before you start sending letters to convicts, you may want to keep reading. We have some advice for you.

Tips for Dating a Prisoner

We know you want to correspond with a compatible inmate but there are steps to finding the right inmate. Have patience, be careful and don’t give out personal information! What I’m saying… don’t be so trusting or gullible. With that said, let’s get to the tips.

Why do you want to date a convict?

There are free men running around here every day and you feel the need to date someone behind bars! You should first examine why is it important to seek someone with restrictions. Are you intentionally looking for a relationship without commitments?

Do you have self-loathing issues? Do you have a secret desire to live the life yourself but don’t have the guts? I mean, let’s face it, people, there are female inmates looking for marriage, so why are you? What can he bring to a relationship? What will you gain? Be honest with yourself.

What it Takes to Date a Man in Prison

Do you plan on getting married in prison? You will spend holidays and special occasions without your husband and that’s sad. How will you cope when you have someone but your mate is locked up? It’s going to take a whole lot of patience and understanding to deal with a man behinds bars.

woman in wedding dress in the dark
Photo by Scott Walsh on Unsplash

At some point, you will need to share your thoughts or get answers to what he is going through even. Do you know of anyone in the same situation? If so, talk with them to discuss their issues, especially if there are children involved.

He can’t help you raise those kids locked up, you realize this, right? I mean, you can’t just talk to him when you want.

Ask About Their Conviction

Find out why is he in prison, to begin with. Is it a first-time deal or are they a repeat offender? Will they ever get out and if so, what are they prepared to change to make their lives better?

Are they continuing their education while incarcerated? What are they doing on the inside that’s positive behavior?

Keep Realistic Expectations

What happens when he gets out? Are you looking for love or someone to help you prosper in life? You know it’s going to be extra hard for him to get a job? Does he have the capacity to be a boss and work for himself?

You know, women are notorious for forming a relationship in their minds way beyond what it actually is. In other words, we go too far mentally. We get married on first sighting in our minds and the guy hasn’t even asked you out on the first date yet.

We do this without thinking logically about the future. Are you prepared to take care of this guy until he gets on his feet?

Does Dating an Ex Convict Work?

Now, I know people go to jail all the time, especially in these days, on a humbug. The police are certainly earning a bad rep… you get no arguments from me about that.

However, at the same time, there are some men who do the crime. They do the time and they get out, and they never to go back. I applaud those who do.

This man will need support, mentally and financially. Are you prepared to be there for him? How about his family? Are they in contact with each other? You may want to examine that matter if he’s not. How does your family feel about you dating a man in prison?

Is this going to be a problem for them and how will it impact your relationship with your family? Sometimes, our decisions affect more than just us.

If this is true in your case, are you prepared to deal with their attitudes and behavior toward you and your ex convict? Whatever your intentions are after he gets out, make sure

a] You get an HIV/AIDS test and bring him along so he can be tested as well,
b] Do the three finger test to make sure he’s a virgin [keeping it real, ladies] and
c] Do a full criminal background investigation. This should be done before you invite him into your home.

If you really want to go through with this, I’m not going to try and talk you out of it.  You never know where love comes from but be careful, ladies, and take your time. Good luck. I hope it works out for you.

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