Dating Someone In Jail (10 Crucial Things To Know)

Last updated on June 11, 2022 by April Maccario

If you find yourself smitten by someone who's currently incarcerated and you are wondering if the relationship can materialize, the answer is yes. It may not be an ideal situation, but many a love story has been written that started when one of the people involved was in prison.

I'm not going to sugarcoat things and tell you the relationship with the person would always be rosy. Dating in the free world is hard enough without the limitations of the four walls of a prison. You will have cold nights and lonely days. There will be times when you will go to bed crying because of the sheer frustration of not being able to share the little things with the person you love.

While there are a lot of men in prison actively looking for a relationship, some really just want someone to use as a tether to the outside. This is not to discourage or scare you; I just need you to know what you're about to get into so your investments don't end up a waste.

When it comes to dating someone in prison, love is not enough. Should you decide to start a relationship while your love interest is still convicted, you will find these following tips helpful.

Tips On Dating Someone In Prison - What To Expect?

1. Prepare To Write A Lot Of Letters

Unlike the outside world where we go on dates to get to know our prospects, dating within the four walls of a prison is quite different. There won't be fancy dinners or the fun outdoor stuff you are probably used to. Letter writing will be your most frequent means of communication, so prepare to become pen pals with your new lover.

You can also communicate with them through phone calls and plan dates around visiting days, but those are limited, so you may not get to say much that way. Writing to your partner may feel archaic, but, on the bright side, it adds a touch of vintage romance to dating.

It is worth mentioning though that you shouldn't be the only one sending mails. If the person you are trying to get to know doesn't reply to your letters, that kind of defeats the whole purpose, wouldn't you say?

2. Ask The Important Questions During The Talking Stage

The only difference between the regular talking stage and yours is that you send letters in place of regular texting. There's also the fact that you can't be as spontaneous as you'd like (prisons have rules). Those are some of the little joys that being on the inside takes out of dating.

The means of prison correspondence asides; what truly matters is that you both make good use of this period to trash the crucial things out. Get to know the man – or woman – behind the jumpsuit, and let them know you too. Ask what landed them in prison, the day they get out, what their plans are, how they spend their time, etc.

Exchange pictures, share your plans, ask for theirs. This stage would be a good time to gauge your compatibility with this person – mentally, emotionally, maybe even sexually. And if it turns out you two are not compatible, executing an exit strategy would be easier now than later.

3. Write More Than You Visit In The Early Days Of The Relationship

It may seem weird that I am hammering on talking, but I have my reasons. Dating outside prison has its challenges, let alone one where you won't get to spend time alone with your partner until his sentence is served.

As if the lack of privacy isn't bad enough, you don't even get enough time with them, to begin with. Absence, they say, makes the heart grow fonder. Having limited access to a loved one only makes you want them more. So, it is understandable that you crave some form of physical connection whenever you get to see.

And that is precisely why you must have known them to a certain extent before this happens. Once you begin to get physical (even if it's only a kiss), the emotions become even deeper. While this isn't necessarily a bad thing, your judgment can get clouded, and that will do you no good in the first few months, at least.

4. Don't Let Money Be The Basis Of Your Relationship

Emotional investment is enough of a risk with dating a guy in prison; don't put your finances on the line too, especially at the beginning. This is a boundary you should put in place to guard yourself against the bad eggs that paint prisoners wrong in the dating scene. These ones only pretend to want a relationship because of what they stand to gain from it (you).

Unless you had a contrary arrangement prior to their incarceration, restrict your spending on your new boyfriend to the essentials only. By essentials, I mean things like collect call charges, and maybe the bills incurred when you eventually start visiting. 

Let them know you are not willing to send them cash or any other stuff that requires you to spend money other than the above. Do this for the first few months at least, someone whose intentions are genuine wouldn't mind this reasonable term. And if they do and withdraw, then you dodged a bullet

5. Be Sure To Find Out If Their Interests Align With Yours

You may need to ask yourself some personal questions before applying this particular tip. What are your expectations of this union? Did you choose someone in prison for a reason, like a psychological need that attracts you to prisoners? A bad boy complex of sorts? Or you fell in love with a man on the outside, and he got incarcerated afterward?

Whichever your case might be, it will do you some good to identify what drives you and see if they are okay with it (vice versa). This puts you both on the same page, and it defines the relationship dynamics. Think of it as the "what are we?" talk. 

If this is just fun for you, make it clear. Don't lead them on to thinking there might be something deeper there. Also, don't assume anything or make plans for a future together behind their back, your intentions may be good, but they may have their own plans too. 

6. Operate Based On How Time Works In There

You will notice I have been using ‘months’ loosely like it's ‘weeks’. That's because time works a bit differently in there than it does out here. Though the person in prison has lots of it on their hands, only a fraction of that wealth of time gets shared with you.

As this person is in prison, you could be exchanging letters and having conversations on the phone, but there's only so much ground you can cover with all of those. So, you two could be celebrating six months of dating, but in the real world, you have only spent about a month or less of that time together.

So, if you are the type who sets relationship milestones based on how long you've been dating, you might want to revise that system and factor prison limitations into the equation. Although, when all is said and done, it is the quality of time spent together that matters and not length. I just thought it was worth mentioning.

7. Notice If They Are Truly Getting Rehabilitated

Even if you have made your peace with whatever crime they committed, it will still be nice to know that they are actually changing. They may be showing you a side of them they want you to see, but there are other ways to know for sure. Unleash your inner detective girl, catch them unawares on visitation days or something.

A surprise visit can reveal if they can be so troublesome at times that it gets them thrown in solitary confinement (Prison Break comes to mind). While once or twice isn't necessarily a red flag, if they keep getting locked up in prison, you should probably take a cue there.

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Also, how they spend their time can tell a lot. Some prisons provide opportunities for inmates to acquire a skill or another. They can choose to work and earn as well. If your beau isn't taking any steps towards self-betterment despite having all that time, it's worth checking into.

8. Celebrate The Special Days And Seek Support For The Hard Ones

There will be tough days, but you'll also have plenty to celebrate together. Their birthday and yours, anniversaries, Valentine's, and tons of holidays. If it's not too much trouble, try not to let them feel alone on such special days. If you can't be there physically, put a phone call through; let them hear your voice.

They may not glorify things like their birthday in their regular life outside, but events like these are usually more profound for them in prison. Even if they are lucky enough to have made friends inside, those people cannot possibly fill the space of their partner.

On the flip side, they can't quite be there for you on all your tough days until they get out, but others can. Join a support group for people in the same situation, your friends may not be enough at times like these. You can draw strength from such forums until your lover can come home to you.

9. Get To Know The Other Active People In Their Life 

Since you started dating, have you come across any family member or friends from their life outside the prison on your visits? If you have, that makes getting to know them a little easier. You can learn something about your partner that didn't come directly from them, for a change. If you haven't, is it because they are estranged, or is he hiding you from them?

A look at their approved prison visiting and telephone list should give you a clear picture of who is still active in their life. You just might find you're not the only woman in their life as they may have led you to believe. I digress.

Getting to know your partner's family and/or close friends is essential, even more so if you two met after they were convicted. Stable family ties mean the responsibility of supporting them when they get out won't be solely on you, so if you two are serious, ask to be introduced. And if it turns out they don't have anybody else, find out why.


How Do You Date Someone In Jail?

You may not get to go on dates like you would outside, but there are still means of communicating with someone who is in prison. Exchange letters a lot, pick up when they call, and visit them when it's right. Some states also allow conjugal visits for unmarried inmates who are in serious relationships.

Do Relationships With Inmates Work?

Relationships are challenging irrespective of those involved, but the chances of success are significantly reduced when one partner is in prison. This doesn't mean there haven't been people who have made it work one way or another. At the end of the day, the likelihood of it working is dependent on the two people involved.

How Do You Show Someone You Love In Jail?

Be open about your feelings for them, remind them in your letters how much they mean to you. More importantly, let your actions match your words. Remember their birthdays and other days that are special to them. Show them love through presents like magazines, food, and toiletries boxes. You can also attach pictures of you to the letters you send.

What Do You Say To Your Boyfriend In Jail?

The same things you would say to your boyfriend if he wasn't in prison. The four walls are limiting enough as is, don't let them define your conversation with your man as well. Although it may help to be more encouraging than nagging, he still wants to know about your good and bad days as usual.

How Do You Tell If A Prisoner Is Using You?

Some signs are not always apparent because some prisoners play the long game. However, there are some things people like that do that should indicate ill-intention. Somebody who is using you will continuously put himself first, irrespective of what you're going through. If he always acts like he has a monopoly on misery, then he's most likely a scammer.

Think About It...

You are not wrong for falling in love with someone who is in prison; you just need to be careful so you don't fall victim to those in it for the benefits. That's where these tips come in. If you find them helpful, please let me know in the comments. Also, share the article, we rise by lifting others.

Do you hate it how everything seems to always revolve round him while you just seem to be an afterthought sometimes?
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It almost makes you wonder whether he actually likes you or whether he's just stringing you along.

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April Maccario
I'm a huge nerd when it comes to understanding how relationships between men and women work, and what drives a certain behavior. I spend much of my time getting into the nitty-gritty and try to share my findings on this site with the hope of making life a little easier for women that are struggling in their relationships or love life.

5 comments on “Dating Someone In Jail (10 Crucial Things To Know)”

  1. In meant someone. 5! Yrs ago I have fell in love with ca guy in prison. His name is. Chris we are engaged. I asked. To send godly he did I really he asked put money so we can or write to each other JPay we see each 2x month he. 3. Hrs from his family loves me & except s. Me. He awesome black &. I’m. White v Do u think I should continue thi? He want Cousling?

  2. I appreciate the plethora of tips on dating an inmate! I’m new to this and I’m still in the reluctant stages because I want to be careful; since I have a tendency of giving more than I receive from previous relationships ( all non incarcerated but a few with priors)! Your column has expanded my POV and clarified a few expectations and the reasoning behind them! Thank you for sharing!

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