Dating a prisoner could be emotionally taxing, but maybe the nuts and bolts of the relationship may be easier than a traditional one? I set out to examine this from all sides, do my research and find out what it takes to date, or be social with a CT inmate.

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I'll tell you what led me to this subject, I was watching TikTok the other night, and in my feed there was a video that opened my eyes to the dating world for incarcerated individuals. Below is the video that made me curious.

@idahoinmates1 #prison #prisontiktok #prisontok #inmate #writeaprisoner #penpal #lgbt #lgbt🌈 #gay #pride #bi #🏳️‍🌈 #ShowUsYourDrawers #fyp #foryou #foryoupage ♬ original sound - idahoinmates1

Chelsea seems to be an attractive and sweet person. Once you put a face to an issue like this, it changes things and you start to wonder more about what life must be like for someone who is locked up. I brought my curiosity to my radio show. We discussed this on the Ethan & Lou Show on I95, Thursday morning (3/10/22).

During the research for the segment, we learned some things. We learned there are way more dating sites/apps for inmates than we ever could have imagined and these are just a few:

Love a Prisoner says their mission is to "give inmates a sense of hopefulness by connecting them to people on the outside world.” Those from all walks of life have committed to our pen-pal service to communicate with inmates and have formed nurturing and unconditional friendships."

Meet an Inmate says it's been connecting inmates with pen pals since 1998. 

Prison Inmate Pen Pal allows you to "write female or male prison pen-pals free. Female and male inmates have address, photo, incarceration details and personal Bio information with direct 'mail-to' contact information for every prison pen-pal listed."

This is all well and good but I tried to do a few test-runs, wanting more information on how a person would contact a CT inmate. I figured there have to be strict guidelines. I can't imagine that every inmate gets an e-mail address and can just contact anyone. I went in search of some of these answers and found some helpful information along the way.

Can you just write an inmate with old school snail mail? 

According to the State of CT Portal the answer is - "Yes. All correspondence must include the inmate's full name and their inmate number in addition to the address of the facility where they are incarcerated. There shall be no limit placed on the number of letters an inmate may write or receive at personal expense, except as a disciplinary penalty, in accordance with Administrative Directive 9.5, Code of Penal Discipline."

Can I just e-mail a CT inmate? 

The CT Department of Corrections has a system in place for this, they contracted a private company called JPAY Incorporated. Some prisoners have access to tablets through this program. Friends and family members of inmates need to setup JPAY accounts. Once they do, they are prompted to add the inmate to their JPAY approved e-messaging list. The whole process can be done through the JPAY website.

Since I need an inmate's ID Number, where do I get that information? 

The CT DOT has a search page dedicated to this where you can enter the person's name and the Inmate ID number should appear. I didn't have any specific inmate in mind so I just searched "Smith" and it seems to work.

Does CT Allow conjugal visits? 

According to the Criminal Defense Lawyer website, CT is one of only six states that DO allow for conjugal visits, New York is another. Investigation Discovery and several other sources make clear that conjugal visits are not easy to get, and there are a ton of reasons you could be denied. I also learned that not all conjugal visits involve sex, or are based around sex.

How often can a CT inmate see visitors?

The CT State DOC says inmates are allowed no more than one 30-minute social visit per week, and that is subject to change based on many circumstances.

If you are thinking of socializing with, becoming a pen pal, or dating an inmate in CT, I'd get a JPAY account setup, get a hold of the ID number/s of the inmates you want to "chill" with and do some research on that person/s specific Institution, and then party.

Important NOTES: The Federal Corrections Institutions like the one in Danbury (Danbury FCI) are regulated by the Federal Government so they have different rules and regulations. My research did not figure for COVID-19 protocols and rules.

Jacob Ammentorp Lund
Jacob Ammentorp Lund

Here is a list of CT Prisons

Prison Hands 2
Dan Bannister

Ask yourself this question, when was the last time you felt in charge of a relationship? When was the last time you had the power dynamic in your favor? For most men, the answer is probably never. Some men would argue that they're always "in charge" of their romantic life, and those men are likely, very single. But, if you date an inmate, you and the warden are in the driver's seat.

Here are some of what I  believe would be the pros/cons of dating an individual that is incarcerated:


  • Power dynamic is on your side.
  • You (with permission) decide when you want to hangout.
  • You can go out with your friends as much as you want.
  • Small gifts like snacks are more appreciated & significant than they'd be in a traditional relationship.
  • You don't have to spend time with your significant other's family.
  • He/she is always happy to see you.
  • You can likely date WAY above your head.


  • You need special permission to be intimate (depending on state laws).
  • The phone bill can become problematic, and one-sided.
  • There is a lot of pressure on you to make the time you have together special.
  • Their friends always ask you for favors.

I think those are the things the challenges and joys of being in a relationship with someone who is behind bars, but I don't know, I've never been in this situation. All my knowledge on the matter come from TV and movies, specifically Seinfeld.

P.S. When I started the article, it seemed like a fun idea for single men and women looking for a different kind of relationship. After doing my homework, it sounds like a lonely headache.


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