By: Matthew Walker, Contributing Writer

Matthew Walker2

So you’re looking for love? You’re one of those who has yet to find that person to walk your journey with. You’ve decided to widen your options to include those who are currently incarcerated. You’ve listed all of the pros and cons and have ultimately decided, why not? You’ve decided there are good enough people in prison who may be worth a chance.

There are men and women locked up that want to walk the walk with you, people ready to commit and contribute to your life. Some want other things though, temporary situations with exclusive benefits to them.

How to find the right one? While patience, perseverance, transparency and good communication are great, here are a dozen additional points to consider. Good luck and be careful!

1) Have you Asked Yourself – Why A Convict?

Why go this route? This is an important step: to list the reasons. Are you having no luck in society? Do you want a situation that more easily justifies your desire to go slowly? Are the restrictions on your time, energy, emotions and other areas of your life limiting your desirability in “normal” dating situations? Are you working on your self-esteem and, for now, need the safety, additional confidence and security that dating a prisoner might offer?

Whatever your reasons – good or bad, sensible or borderline irrational – knowing and naming them is a huge point to consider for a successful relationship. Know what you bring to the table, what you are lacking and what you expect of the other. This is about knowing yourself and your motives honestly.

You’ll need these truths as an extra foundation to buffer the challenge that initially awaits a prison relationship.

2) Do You Understand All That Goes Into A Prison Relationship?

Do you know others in this situation? Get to know people in a like situation for support. They can empathize with difficulties as they arise and can be leaned on for advice, especially regarding the lopsided, seemingly one-way aspects that come up. Though you may receive a surprise bouquet of flowers (more likely a card from canteen), can you accept you’ll definitely not be getting breakfast in bed on your birthday? That you won’t be held tight after a hard day? Can you cope with limited contact and other difficulties? How might you manage if there is a change in their release date? The more you know up front, the better prepared you will be.

3) Find Out What They Are Convicted Of.

Ask them what they actually did. This doesn’t mean they’re likely to do that crime again. What it does mean is that that’s part of their history. It tells you, in part, what to be mindful of. If they’re in for a D.W.I. and their first day out they want to go drinking, maybe that’s a head’s up.

If they’ve remained unchanged, they may still carry traits you don’t want in a partner. A robber, drug dealer, person who has assaulted, sexually offended, or taken another’s life, who has gone unchanged, is for sure a poor choice. Know what they are doing to change, to better themselves.

Ask not only about their conviction but about the circumstances that led up to their choice.

4) Ask When They Are Getting Out.

Do they have an out date? Some may find having a partner in such a limited capacity a plus. I don’t know, but if it works for you, then good. Others may want someone weeks from returning to society. I personally would suggest meeting someone with a little bit of time left. Give yourself a minimum of three or more months to get to know this person.

Why so long? Because this isn’t a normal situation. You can find a jewel anywhere, anywhere at all – but just like when you’re at a garage sale, be careful. There is a reason for discounted prices.

Extra time gives you the best opportunity to get to know them and solidify whatever foundation you can. That may enable you to withstand the weight that goes with their return to society.

5) Are Your Expectations Realistic?

How do you envision the relationship? Give it a try and see how it goes? Or, find a person who’ll fall in love with you, get out and help raise your kids? Help out financially? Fix the wrongs in your life? I’m sure these aren’t your thoughts, but I’ve heard stranger. Whatever your expectations, be realistic with them. If you imagine the person’s return to society to be easy, or the time with them while they’re in prison to be easy, maybe change your perspective. Be mindful that a lot who are getting out have little to no money, and if they do, their immediate goal will most likely be to get situated and stabilize their self.

It is so important to have that talk as soon as possible and to continually update that. What do you expect, anticipate? What do they?

6) Have They Been To Segregation?

If you’re locked up and getting more locked up [put in solitary], that is a sign. The response from friends was funny when I showed them this. They were like, “wait, but I’ve been to seg!” [administrative segregation].

Okay fellows, maybe once isn’t bad, or twice. It depends on the situations. Mainly it is on you to know – how are they living? If they’re reckless in here, without a concern for their losses (meager as they may be) what might they sacrifice out there? Remember, you may start your search for a loved one in here, but ideally you want them to come home and stay home. If they’re in prison for assault and going to seg for fighting frequently, that’s a clue. If they’re in for robbery and going to the hole [solitary] for stealing food from the chow hall, that’s a clue.

If going to seg is never their fault, be careful. An inability to be accountable or responsible, combined with poor decision-making, should be further clues.

7) Are They Working? What Do They Do With Free Time?

Across the U.S. prisons are different. Perhaps some aren’t allowed to work elsewhere, but here all are. If the person you meet doesn’t work or go to school while they are in prison, what do you think they’ll do when free? The same thing. In here, there is time, more time and then extra time to do most of what you want to do. If they can’t make time for work in here, where skills are of no real consequence, what will they do out there?

If their time is spent watching all the TV series and talk shows, if they play cards all day, then what aspirations do they have? If you don’t mind this, great, but know to inquire ahead of time so you at least have a head’s up on this. There are opportunities in here to better one’s self. If not in here, why out there?

8) Are You Sexually Compatible?

In the absence of conjugal visits in most states, how do you know if you’re sexually compatible? Phone conversations and erotic letter writing are ways to gauge if a spark exists. It’s also a way to discern what other issues may be at hand. During talks, are they more inhibited than you’d like? Too explicit? Do they talk about things you’ve never heard of or never thought to try before? Do they have a preoccupation with sex?

Every bit of information is a clue to better knowing your potential partner. If they repeatedly talk about sex from behind – maybe that’s a clue?

This is one of the safest and earliest ways to test compatibility while still locked up.

9) Who Is On Their Visiting List?

Who comes to see them? Do they have multiple names there? Do they have a lot of women “friends”? If they are reluctant to show you their approved visiting list, is there a reason? (I’ll probably be hated for naming this one, but it’s important.) Perhaps those names are your competition. The same way you are looking for love, others are as well.

All prisoners have access to their list, so ask for a copy. While looking at it, see how many of the names say “family” next to them.

10) Are Their Family Ties Intact?

Do they stay in contact with family? Are they estranged from them? What level of contact do they have? Some families lacked closeness prior to the person coming to prison. In other situations, the separation was a direct correlation to their behaviors. Did they sell the family television? Did they steal silverware, jewelry, the family dog? If unable to mend family ties, if they lack the desire to do so, those could be indicators.

People who have more support and connections tend to do better upon release, giving you and your relationship one less struggle to manage. If family relations are stable, when it’s time, ask for introductions.

This prison environment is so sterilized and neutral, it doesn’t lend itself to showing off personality. Family accounts can add a depth to your understanding of your prisoner’s naturally occurring mannerisms and quirks.

I’ve been in prison for years with some people, then one day I see a photo of them in the free world, or overhear them with their family in the visiting room – and I’d have sworn this was a wholly different person. Don’t be surprised.

11) Is There False Advertising at Play?

Is this person who they represent? What are the subtle and glaring misrepresentations? We all have them, even in the free world. Women have their hair extensions and whatever other enhanced aspects to them and men do as well. It could be as simple as faking fashion sense and style. When all must wear the same prison issued clothes, it’s easy to fake.

Most everyone has ‘Photo’ clothes and ‘Visiting’ clothes that look nicer than their other clothes. No subterfuge at work there, but the disparity between one’s daily clothes and visiting clothes is a clue. Some people in here, if you see them daily, you’d think they never got out of bed, the wrinkles and such. When they have visits, that’s the only time they clean up.

Do you really know about their hygiene habits? Are they who they say they are? Are they nice? Are they smart? In here there are many ways to make money, selling artwork and the such, but another one is letter writing. People pay others to write their letters, so they don’t appear as illiterate or poor with words. When getting to know someone, be sure you’re getting to know them. If how they talk doesn’t match the style in their correspondence, that’s a clue.

12) What Are They Committed To?

Do they have obligations when getting out? When the two of you discuss plans for the future, are their talks surrounding THEIR plans, THEIR dreams, what THEY need and what THEY are going to do? Be sure your relationship is two-way.


Hopefully, these tips help. One benefit for extending your romantic options to include those who are incarcerated is that you’ll get a higher level of captivated interest and a heightened receptivity to relationships. Love can be found anywhere, and with work, it can flourish. But! Be mindful and be careful. There will be enough naturally occurring difficulties in developing a relationship, don’t let the above add to them. Have realistic expectations and be wary. There are scammers and those with a limited capacity to truly know others on a deeper level.

No matter how mindful you are, there will be challenges. Good luck!


Matthew Walker is serving 15 years in Minnesota for criminal sexual misconduct.


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Matthew Givon Walker #158836

Moose Lake CF

1000 Lakeshore Dr.

Moose Lake MN  55767