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The Complete Guide to Dating in Jail

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It’s love that makes the world go round, right? Even in jail? Yes, even in jail. With more than 2.5 million inmates currently languishing in U.S. prisons, that’s a lot of potential partners who are, well – otherwise occupied, let’s just say. But that doesn’t mean they can’t also find love. Here’s the complete guide to meeting the girl or guy of your dreams, even if one of you is enjoying the state’s hospitality. Relationships are typically long-distance and many are by correspondence only, but for those who find something special in each other there’s always the chance of a match that can outlast the inmate’s sentence.

Find the One

Online DatingBefore you can start dating someone in jail you need to find an inmate who’s interested in you. There are now a number of online dating sites such as Meet-an-Inmate, WriteAPrisoner, PrisonInmates, InmateConnections, Convict Mailbag and InmatePassions where male and female inmates can have their profiles posted with an attractive photo of themselves. Inmates don’t have access to the Internet so the accounts are usually opened on their behalf by someone else, but they include their real names, photos and a short bio.

Convicts will need to get someone to set up a profile for them. Those on the outside, however, can start the search by visiting the various websites that focus on inmates. Select the gender and age group that interests you and view the various profiles until you find one that resonates with you. Some sites offer links to platforms where you can verify the identity of the prisoner you’re interested in dating.

Make a Connection

When you write your first letter to the inmate of your choice, you’ll need to provide a fair amount of detail to introduce yourself.

Make the initial connection by explaining:

  • Why you want to become pen pals,
  • How much of a time commitment you’re prepared (or able) to make.
  • Be respectful of the person’s time—even if they are serving a sentence it doesn’t mean they want to read fluff
  • Address the envelope exactly as shown, to make sure the letter reaches the right person
  • Include a photo of yourself and a description of your interests and hobbies.

Take It Slow

Just because one of you is locked up doesn’t mean you should rush anything. After all, the inmate is a convicted felon and you only have information provided by the prisoner themselves. You can do a basic check online that their name and other details are correct, but it’s vital that you get to know each other thoroughly through your letters.

What to Write

Ok, this one’s a doozie. You can write whatever you want, but remember there’s a good chance the letters are going to be intercepted and read by prison staff to ensure there’s nothing in them that contravenes the law. So you can’t plan the latest episode of Prison Break with your penpal, capiche?

You might also want to think twice about getting hot and steamy, because you never know when something might get “leaked” online. I’m not saying you shouldn’t do so, just that you need to be sure you have nothing to hide from anyone if you do!

Planning a Future

Inmates who establish positive relationships with people on the outside are less likely to return to a life of crime once they’ve done their time, so there’s no reason not to plan a future with your penpal—provided, of course, there’s a projected end to the sentence! Life sentences without parole are a bit more difficult, because chances are good you might never get more than a monthly conjugal visit and you have to first prove a long-term relationship to achieve that.

The great advantages of dating someone in prison are that usually, competition for the inmate’s attention is low (duh!), issues such as age, body size and shape are incidental. Also, any relationship formed is largely non-physical and is built mostly on each other’s fantasies. So for anyone longing for more of a mental connection with a lover, this could be the answer you’re looking for.

Macbook Pro by Jeff Geerling / CC BY 2.0

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