Prison Letters and Why Women Love Men in Prison — The Re-engineered You

Todd Lemense
5 min readJul 7, 2020

This episode is about prison letters. The interest came when I received a letter from the Oregon Department of Corrections. It was from an inmate, and he was addressing someone he seemingly had a connection with in the “outside” world. The handwriting was perfect, the words flowed very well, and he clearly was trying to reach out to a woman who most likely lived in my home before me.

Though the letter never reached the person it was intended for, it did spark significant questions, such as why do prisoners attract women so well? Does real prison love exist, or is it all a scam? And how do these prisoners learn to write so well in the first place?

Myth: Women Must Be Twisted to Fall in Love with Prisoners Hybristophilia

When it comes to having a strong attraction to societal deviants, criminals, and prisoners, Hybristophilia comes to mind. This is a paraphilia where people are aroused by people who have committed outrageous acts, such as cheating and crimes, including rape and murder. The thing that makes this so interesting is that it is different for everyone. Some are more passive about it, while others are aggressive.

· Passive Hybristophilia: This is when someone is drawn to criminals, but they do not act on it or try to assist them in any way. They may show passion through being an advocate for the prisoners, or simply enjoy movies such as OITNB and Prison Break on a deeper level.

· Aggressive Hybristophilia: This is where trouble can arise. These are men and women who proactively help the criminal they are attracted to. This means they could lure victims in, cover for criminals, bury bodies, and other severe acts. Bonnie and Clyde are the perfect example of this type.

So, why do so many prisoners/criminals in relationships? The answer is quite simple. It is a mixture of Hybristophilia, the desire for excitement from their mundane lives, the long-distance passion, and the fantasy of it all makes people drawn to that lifestyle. In fact, there are over 40 different websites that cater to prisoner dating, such as

Potential Consequences

Though it would be nice to have a happy ended every time, there are significant consequences from dating a known criminal. For example, a book called “Dream Lovers — Women Who Marry Men Behind Bars” by Jacquelynne Willcox-Bailey talks about a real-life incident. Two sisters walked out of their long-term (boring) relationships to get with prisoners. When those men were released, one of the sisters was murdered, and the other was beaten and tortured, which sent her supposed lover back to jail.

With this as a possibility, always be aware of the dangers you could be subjecting yourself if you decide to follow that journey. With that being a solid case, does that mean that all prison love is fake, and they are nothing but predators?

Myth: There Is No Such Thing as True Love in Prisoners

There are some genuine and sincere relationships, but there are also tons of scams as well. How do you know the difference? If you are reading a letter from someone behind bars, and they ask for money in any way, it is likely a scam. Do not fall for it. They could either be reaching out to women and men for financial gain, attention with the media, or to gain supporters, just like Ted Bundy, Richard Ramirez, and Scott Peterson did.

For the record, serial killers such as those noted above are less often associated with scams and writing letters. You may think that they are great at manipulation, but that is not the case with them. They get away so well with murders and crimes because they are bold, always act like they have nothing to lose, and never overthink what they are doing. With an IQ of below average, more love letters come from non-serial killers who are much smarter and think things through better.

Overall, use your best judgment. These people will not always con you, and they may be truly into letter writing for human connection. There are many people in jail who do not have family or friends to reach out to, so they turn to pen paling to feel involved, valued, heard, and feel like they matter. Though it may not always be about love, it can still be about companionship and support and worth volunteering to help people such as them feel cared about.

Bonus — How to Craft A Prison Letter

One thing I noticed the most about the letter I have how well written it is. There are no errors, the penmanship was nearly perfect, and the message was very well contrasted. So, how did someone in prison learn to write so well?

One word: practice.

Those who write love letters would use trial and error in their writing. For example, they would keep tabs on the responses they would get from their “loved ones” when they said certain things. They would then work on perfecting in those areas to get even more positive responses. In addition, they could also have utilized other inmates for assistance as well. More perspective is a catalyst for fostering new ideas and learning how to write a moving love letter, or scam someone successfully.

If you want to learn to write a great letter, start with practicing, use your feedback as a guide, and never be afraid to ask for help so you can become a pro.

Final Thoughts

Falling in love with criminals and prisoners is Hybristophilia. Though having this characteristic in a passive sense is fine, seek help if you feel like you will act on those passions. There are limited professionals that can assist, but it is worth finding a reputable person before you do anything drastic that could land you in jail yourself.

Remember, human connection and writing to prisoners is a great way to improve their quality of life. If you are talking to someone who has no one else on their side, keep being a hero to them. But always know the signs and be mindful if they are trying to scam you or not. The last thing you want to do is fall in love with someone behind bars, only to find out they were using you for personal gain.

As the last word from us, we don’t know everything, but we do have an opinion on everything.

Todd Lemense

Originally published at on July 7, 2020.