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Why do some women like to date inmates?

Updated on February 25, 2018

Yes, indeed...why?

Who the heck knows - but it's an affliction that ought to be treated, that's for sure. Finding the answer to this complex and rather baffling condition that strikes women of all ages and from all walks of life is not easy for just those reasons - these gals are of all ages and from very different backgrounds. One thing is certain; whatever it is that makes these girls fall in love with criminals, it's simply not a good move.

So what could it be that makes dating hardened crims so attractive to some people? If you think about it logically, it makes no sense. To anybody who isn't emotionally involved, it is hard to find one, let alone more, compelling reason of why a seemingly sane person should look for love that way.

Having given this a lot of thought (for reasons we need not go into), the following might shed some light on why a woman might want to date a prisoner (though it doesn't explain why she goes through with it).

These girls don't think much of themselves so they will appreciate anyone who looks at them.

Some girls feel that being in a relationship makes you complete. I suspect it doesn't take much to be 'in a relationship' with a prisoner, so it's really a quick fix to fill the void, so to speak, while you're searching for other options on the 'outside'.

  • She would like to date a handsome and/or younger man

Let's face it; inmates have time to work out and women find a good body attractive especially if, in real life, these girls haven't had the opportunity to lay their hands on someone good-looking... A hint, ladies, coming your way: If good-looking guys are passing you by, there's a reason for it; look over yourself critically and work it out (literally in some cases)... which leads us to suggest that:

  1. She's an ugly trout and feels she's out of options (There I said it! How dare I!)
  2. She's drop dead gorgeous and just wants to spread it around
  3. She works there
  4. A combo of any of the above
  • She likes the idea of having someone who will admire her and tell her how special, beautiful and wonderful she is

All women like to be told they are beautiful. Inmates take advantage of this desire to seduce receptive girls by flattery. Women crave this type of attention and are basically vulnerable to this sort of exploitation by nature.

  • She's so kind she's a true innocent and will only believe what she wants to believe

There's no help for that sort of mindset, unfortunately.

  • She likes being in control of the romance and the entire relationship

Women who may have experienced abusive relationships in the past might want to date inmates; preferably those serving a life sentence without parole. This is the safest kind of relationship for any woman really simply because the man is not physically there so there is no possibility of the relationship turning violent.

  • She's intent on keeping the relationship at the 'romance' level

Quite often, these girls never get to have any physical contact with their man so the entire relationship is played out in their minds; once again, the script of how the romance unfolds is entirely theirs.

  • She's hooked on the correspondence she gets from the inmate/s

Inmates like to write letters to women for two reasons: they are bored, and to recruit more people to their cause. The cause usually involves getting money from the women to pay for extra food or fund appeals on their behalf etc etc.These fellows need to get as many people as possible to help them so they develop a real flair for reeling vulnerable girls in. And who could blame them? If you were stuck in jail for a very long time, you might want to do the same. I know I would. It would certainly help pass the time...

  • She must know where her man is at all times

Some women are so insecure that they simply must know where their man is 24/7. Dating a prisoner gives them the security they seek.

  • She wants to help him

Never mind that she might need a lot of help herself, she's determined to help the less fortunate no matter what the personal cost.

  • She's looking for a soulmate

And now she may have found him 'cause the dude will feed her whatever she wants to hear in spades.

  • They went to high school together

Back then she thought he was hot; he thought she was not. Wait a minute! That's not right. Back then he thought nothing of her 'cause he never noticed her... But now he's changed his mind. She hasn't.

  • She met him at a bus stop once and now they've rekindled


  • She's Juliet; he's Romeo

Awww... that's just beautiful. I wish them well.

And...tadaaahhh! Drumroll please...

  • Could it be that she's simply an idiot?

I'll leave that up to you to decide.

And on the flip side:

  • She's really well adjusted but bored s***less in her perfect life so this is her way of spicing it up
  • She's perfect in every way and is looking for a great friendship with a view to a great relationship and doesn't mind the wait
  • She's writing a crime novel and needs to research
  • She's lost a bet
  • She's made a New Year's resolution to get to know people from a different walk of life
  • She's a popular girl who has exhausted the pool of available men in her neighbourhood so she's venturing out
  • She's quite kinky in ways we need not go into and this just fits the bill
  • She ain't got two brains cells to rub together (on top of everything else that's in the mix already)
  • She's obsessed with the minutiae of her daily goings on and has selected inmates as the target group most likely to appreciate that sort of correspondence, and/or
  • dating inmates has become somewhat of a tradition in her family so she's just keeping up the expectation, and finally
  • she's such a sad sack she doesn't recognize herself in any of the above insisting that her love affair is just another, normal relationship and will defend herself vigorously in the comments. Good for her.

The above list is not set in stone, obviously, as stupidity is a bottomless well, but the list represents all I could think of. If you have anything to add to this, feel free to do so in the comments. BTW, you do realize this is for your amusement only, don't you? So let's just keep on keeping it real, is all I'm saying.

Can dating an inmate ever work?

It probably does for a whole bunch of people, for a while. Some girls will take the jailhouse romance for what it is - silly letters to make them feel good - and that's where the relationship will rest; but other girls will lose their heads altogether, and that's when it gets ugly.

The following account is a true story.

When Sandy met Harry - A Jailhouse Romance Worth a Bucketload of Teeth

A woman I know, let's call her Sandy, was trapped in a loveless marriage with a violent alcoholic. Not a pretty picture, I know. Nobody would have blamed her if she divorced him and went on her way (yet again). In hindsight, it would have been the best thing for everyone involved. However, Sandy chose a different path to resolve this unhappy union. Here's what she did.

On the quiet, Sandy began corresponding with an inmate, an armed robber with a 10 year sentence. She got hold of him through an acquaintance, who at the time was also dating a convicted felon. After a while, on the pretext of visiting her ailing mother in another town, Sandy began regular visits to see this man, and correspondence intensified, sending hearts aflutter until eternal love was declared, sadly on both sides. Still, no harm would have been done if love letters were all that was ever going to happen. But things took a more serious turn when the feller was let out.Though he was unemployed, unemployable, suffering B.O. and burdened by mental issues and practically broke, Sandy, in the face of all this, reaffirmed her love. Spurred on by his poetic declarations of passion and everlasting devotion, she packed up her two young children and left the state to live with the newly released poet somewhere stupid. And they all lived happily ever after...

Not quite. Unfortunately, the story continues...

In comes Sandy's husband. Sandy's hubby, a sad and moronic creature to be sure, had somehow, despite his pervasive alcoholic haze, gathered enough wits about him to take legal action to recover his children. After a bit of a to and fro, the courts decided that Sandy must return the children to their rightful home as her place was judged to be an unsafe and unstable environment. Sandy's response was to promptly go into hiding with the children, then go on the run with them and her new man. After a couple of turbulent weeks spent traveling erratically up and down the coast in a van, the fugitives were apprehended and the children returned to their father, who, rather magnanimously for such a dolt, decided not to take matters further.

And why was this man so reasonable, I hear you ask? The answer is nobody knows. We could take a guess and speculate why this wronged man chose to be so uncharacteristically level-headed after what Sandy had put him through, but it would do us no good. Maybe he was plum out of cash to sue her. Maybe he was planning an elaborate and horrible revenge. Maybe. But I prefer to give him the benefit of the doubt, and give credit where credit's due. Sandy's hubby chose to end the feud simply because he had the kids' best interests in mind.

And now, let's go back to our love-struck inmate-dating gal. Did she find the love and happiness that she fought so hard for? Well, that would have been too much of a fairytale, wouldn't it?

Poor old Sandy swore to stand by her man, through thick and thin. Theirs was a love story worth hanging onto, Sandy declared and promptly moved with her ex-con to another state, thousands of miles away from her kids, to enjoy the romance in peace. However, things did no go according to plan. Predictably, after a few more weeks of unwedded bliss, this trailer park romance took a violent turn. In a drunken rage the inmate took a hammer to the trailer, busting out the windows and the cooktop as well as Sandy's few remaining teeth (she had been married twice before, you know). It got a bit heated and s**t went down, as Sandy put it, reluctantly admitting defeat from her hospital bed where she landed after the trailer went up in smoke and the inmate was hauled off to the watch house. The erstwhile love-struck Sandy, now drinking soup through a straw and consequently in a much more sombre mood about the entire relationship, conceded that she had made a BIG mistake moving in with a hardened criminal. The upshot of the romance was the loss of her children, her teeth and her credit rating. Yes, Sandy was now twelve thousand bucks in debt despite having a full-time job because, while Sandy worked hard to make ends meet, her happily unemployed convicted felon had been busy gambling her money to relieve the boredom he felt at home.

So, what can one say about this sad end to this very sad story? Truthfully, not a lot. Obviously, it did not end well. It was never going to. Everyone but Sandy saw it coming but were powerless to stop it.

Two years later Sandy admits that moving in with a newly released inmate wasn't the cleverest thing she ever did but it wasn't the stupidest either. The most irresponsible decision was to let this crazy dude near her children. Having regained her senses, Sandy realized she had put the kids at risk, just by allowing this fellow near them. Well, all's well that ends well, right?

Hopefully. But just recently, when this situation was rehashed (yet again) Sandy was asked by a curious friend what it was that drew her to the inmate to begin with, as none of us could see it. To this Sandy replied that she thought that he was handsome. Oh dear, the company shuddered, the room suddenly filled with a sense of foreboding as we all realized where this was heading... Just the other day Sandy moved another handsome man into her trailer. (Stay tuned for an update, which you will find here.)

So the point to this cautionary tale, in case you've missed it, is that dating an inmate is NEVER a good thing! Seriously!

... With that said...

Are you a likely candidate for a prison romance?

Most of you reading this right now would probably disagree. But who knows what lurks beneath your everyday hum-drum facade? Secret desires you are too afraid to acknowledge, perhaps?

Take the quiz below to find out if you're likely to seek romance behind bars.

Which one of the following would have to happen in your life for you to date a prisoner?

See results

Do you have a secret desire to date a prisoner?

view quiz statistics

Ladies, ladies, ladies! Lighten up a little. If the shoe fits... if it don't, it's just as well.

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    Post Comment

    • profile image


      2 months ago

      I suggest that the one type of woman you propose, doesn't exist. I do, however, have an alternative type of woman, or situation, that might cause a woman to want to date a felon.

      First, the non-existent woman:

      "She's really well adjusted but bored s***less in her perfect life so this is her way of spicing it up"

      I don't believe that a well adjusted woman would ever allow herself to get THAT bored! Seriously, if someone is well-adjusted, I would expect her to either be happily married and busy, with a husband and kids, and a great social life, or single and dating men who are actually able to pick her up for dates, and give her a great time. Writing letters to an inmate would be a whole lot more boring than dating a flesh and blood man (notwithstanding the suspense and anticipation provided by the possibility that an inmate boyfriend might come after you and slit your throat, if he ever gets out!)

      My alternative suggestion is:

      • a woman who wants her husband murdered (possibly for financial gain): she may try to get a violent inmate to fall in love with her, so she can get him to kill her husband, once he is released. She may find she has bitten off more than she can chew, in the end, though!

      As for some of the very offended, defensive women who have responded, previously: (a) it was obvious to me that you were referring to women who started dating men after they were incarcerated, and (b) most women who do "fall in love” with felons tend to go after very violent murderers and/or sex offenders. Sadly, they seem to be very eager to be convinced that the man is totally innocent of any crime, or he’s really, really sorry, and of course he would never do it again! If he’s particularly good looking, she’s likely to be one of many women, flocking to believe this “poor man”! Because, who wants to believe that good looking men can be killers?! If she’s very lucky, he’ll be in prison for the rest of his life. If she’s not, it’s a toss-up as to which of them will have a shorter life, but if he has killed before, my money would be on her!

    • profile image


      2 years ago

      Thank you for being a perfect example of what needs to be presented to congress & other government officials. It's sad that USA citizens are seen as unworthy or "free to be judged" because their hearts are invested in an inmate. Even more sad that lawmakers realize 20+% of them need rehab or a psychiatrist instead of 10 years behind bars. I'll pray for you.

    • profile image


      2 years ago

      I started dating my boyfriend before he got locked up. Everybody has a past weather its good or bad. and for you to judge a person shows how you view things is negative. not every women who is dating a guy in jail has low self esteem or is despite need of a relationship.

      So if you went out and commited a crime and got locked up would you want your spouse to leave you? I wouldnt i mean depending on how long i was in there maybe. but I love my boyfriend and i will stand by his side no matter what he gets himself into. because that is what a relationship is. standing by your partners side through good or bad. but everybody has their opinons on this matter but its just that opinions. dont speak on something you know nothing about. I am a christian and i follow the word of the Lord and he is the one who lead me to my man.

    • profile image


      3 years ago

      I use work in a jail and they use to brag about how they use to get women. All the women I knew who fell for that were either hurt or Dead and I know 2 women who are dead. It may not happen now but it will happen later

    • profile image


      3 years ago

      I found this hilarious! My fiancé is an inmate. The whole thing is, I didn't know he was an inmate until after we started talking. Lol nice try though

    • profile image


      3 years ago

      I like reading others options, was this from personal experiences? It sounds like you know your facts. I am just curious how you pulled these statistics.. You spoke of an Inmate like they are not human. Every person is held accountable for their actions. God sees and knows all. Not every inmate is inhuman or unable to change. You are putting all inmates in one category and all woman associated with them in one category. Things happen life goes on. So how's your love life? Sounds like you have it all together. :)

    • profile image

      A. Hatfield 

      3 years ago

      Although I do believe some of this article to be true, it does not fit all relationships. My husband and I did go to high school together (that actually got a laugh from me), and neither of us noticed one another. We were in totally different circles and completely different times in our lives. I am a paralegal and have dated plenty of very attractive, fun, loving men in my life and we have gone our separate ways on our own. I am very dominate, independent, hard working, have a ton of great friends, wonderful family, and I have never been self conscious. With all of that being said and taken into consideration, I went seeking for my now husband who is an inmate. He is doing a 10 year sentence and I have waited almost 5 years for him. I approached him just to show support. It started as a great friendship. He was very flattering but I was used to men being this way anyway. I fell in love with his positive attitude, his extreme support and understanding and lack of judgment towards me. He is a happy man, loving, and although most women do support these men financially, he was sending me home money, flowers at work, etc. He had been on the news for running a youth program and is very well known, respected and liked by many community officials, judges, the list goes on. I can agree sitting in a visiting room watching a mid aged woman cuddling up to a 20 year old while he looks like its forced, I can say that this article fits some. But this article does NOT fit my story and I know this to be untrue for marriages that have worked out and had a "happily ever after" just for the simple fact that the inmate actually appreciated the woman that stood by his side in hard times. Just like all other things in life, some stories are good, some....not so good. But don't bash us for what we are.

    • profile image


      3 years ago

      Whoever edits and puheisbls these articles really knows what they're doing.

    • Tina Asalina profile image


      4 years ago from Alabama

      Ouch! I think criminals are everywhere many just haven't got caught. So therefore they don't have the title inmate or maybe they will never have it. To make a long story short, most of the woman that are in treatment has relationships with an inmate because it's someone from their past. Believe it or not they or inspirational to each other. With that been said to each it's own.

    • profile image


      4 years ago

      You are so wrong and offensive its shocking. I am one of those women and do not fit those categories. I suggest its you that needs a life, not me.

    • profile image


      4 years ago

      Also, the sense of danger can be rather attractive and intense. A strong, dominate, dangerous man can intrigue all kinds of woman. Someone who is tough.. ya know.


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