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He's in jail now. When he gets out do I tell him I was a prostitute and other things about my past?

Tagged as: Big Questions, Family, Online dating, Troubled relationships, Trust issues<< Previous question   Next question >>
Question - (4 October 2013) 25 Answers - (Newest, 5 October 2013)
A female United States age 30-35, anonymous writes:

So I'm talking to a man, who is currently in prison for a charge he caught at 17, for burglary.

He gets out in 12 days, and I plan on spending time with him. We write all the time and I have met him. My problem is, he wants to know me, like really know me. My past, my ups and downs, etc. I have had a semi hard life.

At one point in time, I'm ashamed to say it, but I was a prostitute. I only did it about 6 times. I had my child taken away due to drugs (he knows this) and my parents were incarcerated. I literally had nothing. It took a year to get my baby back and get on the right track. Since then I have gotten my little boy back, acquired a job, have a car, and am stable. I am scared to tell him about some of the shameful things ive done.

Should I not let him in that close? Or just be honest? Im scared of what he might think, especially of the selling my body part. His past isnt great but we were both kids. I need help.

View related questions: drugs, in jail, prostitute

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A male reader, Stoney1215 United States +, writes (5 October 2013):

You are ok with him being in prison currently. The least you should expect of him is him being ok with your past. Im mean seriously he is a convicted felon do you really think you should accept him looking down his nose at you.

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A female reader, anonymous, writes (5 October 2013):

You could tell him there are things in your past that you are ashamed off and that you would rather forget. That it hurts too much to talk about them and that one day, when you have known him long enough and feel comfortable enough .... you MAY talk about it but until then you would rather focus on your future because you learnt the hard way about how low one can go in dire situations and how hard some regrets are to live with. You want to build a future, not dig up the past too much.

If he truely cares for you, he will accept that answer.

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A reader, anonymous, writes (5 October 2013):

This is verified as being by the original poster of the question

Thank you everybody! You guys have truly been very helpful to me and I thank you all for takin the time out for responses! :)

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A female reader, CindyCares Italy +, writes (5 October 2013):

CindyCares agony auntPardon me, I don't mean to be witty at your expenses, and I realize that this for you may be a dramatic situation, but.... for real ?! You are afraid that a BURGLAR may look down at you because of your shameful past ? Hey, what about HIS shameful past ? At least prostitution is legal in many countries, burglary is illegal EVERYWHERE !

Anyway : you may be an ex prostitute but you are currently a MOM of a young child. Think long and hard what kind of people you want your child to be exposed to, to grow up with, to take as his role models- and ask yourself sincerely if THIS guy is the best you can offer him from this point of view. It's not all about you and what YOU want and like- you have to think of your child's wellbeing and future first.

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A female reader, Aunty Babbit United Kingdom +, writes (5 October 2013):

Aunty Babbit agony auntThank you for your responses :)

You certainly sound to me like you've thought it through.

Please just don't be ashamed of your past, it has made you who you are and, if he's a lovely as he sounds, he will understand and respect the hardships you faced.

It may even bring you closer because you've both done things as kids that you regretted and have both paid a high price for them but have both turned it around.

I wish you happiness.

Hope this helps AB x

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A reader, anonymous, writes (5 October 2013):

This is verified as being by the original poster of the question

I plan on making him prove it. I have put my heart out too much to just let it get stepped on again. I will never risk losing my child for anyone again, not even myself. I plan on making him show me progress, show me that he wont do drugs, or steal. That he'll work, and show me the qualities I look for in a man.

He served two years. It was a family dispute. Now he still keeps in vontact with that family member. I dont plan on jumping into marriage or making him my sons step daddy so soon. I want to take things slow. I'm recovering from a heartbreak caused by moving too fast already. That guy told me there was no such thing as moving too fast, then proceeded to leave me because I wouldnt move in with him, in less than six mo ths of being together.

I want to go slow, and get to know someone. I want a connection thats more than physical. If that makes sense.

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A male reader, dougbcoll United States +, writes (5 October 2013):

dougbcoll agony aunt "should i not let him in that close ? or just be honest?" well if your relationship with him or anyone else grows or goes anywhere, not being honest well more than likely eat at you. i believe you would not be posting for help on this subject if it was not true.

we all make mistakes and may have done things we wish we would have done different, or not have done at all at some point in our lives. most of us regret things we may have done that may have happened at a time while we were young and not thinking about the future or how it would impact us or others around us and in our lives.

but everything we do in life effects not only our self, but also people that are in our life. the thing is to learn from our failures, mistakes, and go forward. to try and be a positive effect in the lives of people we come in contact with.

as i always say relationships are built on love, trust, and honesty. those are some of the foundations a relationship is built on. where ever your life may go you have lived and learned from mistakes, go forward , and be honest with yourself and others. if you don't let people in close to open your heart to them, relationships will be just on the surface and not able to get to a depth of the real you.

this is my perspective and i hope it may help you.

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A reader, anonymous, writes (5 October 2013):

I feel much better than I did when I initially wrote my first response to your post. I have a lot of concern for you. I realize how hard a mother who lost her child to child protection authorities would have to work to get their child back.

A good friend of mine is an attorney for the state in this department where I live. He has told men dozens of horror stories. Not to mention those I've read about or heard about on the news.

It's not just about you and what you want; but what is best for the child. If there is any possibility that the environment of that child is not safe. You will once again have to release the child to the custody of child protection authorities.

Conscientious neighbors and family members may intervene, if by any chance the child is at risk. I also have concern for your well-being.

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A reader, anonymous, writes (5 October 2013):

This is verified as being by the original poster of the question

*continuing my last post, I accidentally hit the post button on my phone.

I feel more comfortable because he's taking it upon himself to go slow. He tells me when he gets out he wants to be stable before we jump into anything, that way we wont have to stress all the time.

He asks me what I want to do with my life, where do I see myself in ten years, how do I feel about my son going to public school, etc.

I dont knoq, my family is full of convicts, both my parents are as well, so I know how they usually act. He just seems different.

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A reader, anonymous, writes (5 October 2013):

This is verified as being by the original poster of the question

To be honest with you guys, more specificly Tisha-1, I also used to work for the prison he was in. I never had any issues with him and never crossed prpfessional boundaries while there. I quit because as I said, my son was taken because of my drug use, my job and place of living was too far for me to juggle 12 hour shifts, visits, drugs tests, mandatory therapy, and meetings with caseworkers. It was stressful, I quit and moved back to where I got in trouble at, where my family lives as well, got a new job & am doing great.

As for him, let me tell you about him, he is 24 now. He doesnt hit on me in every letter, not even close. He tells me he will not be happy if I send him money. Says save it for me and my baby. He tells me about his family. Talks about nature, astrology, things of that nature.

His dad is a superintendent of a drilling company, so he has a job to start off with when he gets out. He talks about how he doesnt want to go through this again, and he will never settle for less. Making it by just doesnt cut it.

I think that the fact that he's actually the one going really sloe,

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A female reader, Abella United States +, writes (5 October 2013):

Abella agony aunthe's been in prison where STDs are rife and where drug taking does occur.

What skills and lessons has he learned in prison to make it a little easier to get work.

You most certainly should not be expected to give him free accommodation and home comforts when he gets out of jail. He has to learn to stand on his own and start looking after himself.

Is he likely to want to be friends again with other people who encouraged him to do things that landed him in jail? We are the company we keep.

He may also be in no mood to wait for sex with a woman since he's ben incarcerated for some times.

And to protect you and your child you deserved to be allowed to take things slowly since there are some risk factor surrounding him.

You have met him and have seen him face to face. Interest and infatuation and extreme curiosity about a person are no match for integrity and respect and empathy. Meeting him on the outside may introduce new pressures into the relationship.

The reality of seeing someone 24/7 can mean a loss of connection. Or big tensions can arise.

I would explain to him that it is in your best interests to take things slowly. Find out how judgemental he really is.

Men in jail sometimes target a woman with a child just so that they can get closer to the child. Some such men do actively attempt to abuse a child. So please be careful.

And this is also very much about you. So you need to protect yourself. I think men just out of prison can be a risk to any woman.

In such circumstances men just out of prison are not the best of guys to start a relationship with, especially as you have a child, and your child must come first.

Meet him in a public place for coffee, without your child present, once he is out of prison.

Get to know if he loses his cool too easily or has a temper - you do not want to find out too late that he has no empathy, or is cruel, or loses his temper too quickly.

Wait until you know the man better on the outside before your child meets him.

Do not leave him alone to babysit your child if you need to go somewhere.

And as far as you revealing all? Six times is a transgression on your part.

You should not expect to have to pay penance for the rest of your life for this.

And extreme caution at the outset about not telling all immediately. You do not know this man as much as your think. Mixing with some brutal men in jail can lead to a person using solutions that may only work in jail, sometimes.

Because if the relationship turns sour he will throw back at you all that you said to him and likely twist it to really hurt you emotionally. Or tell others. As I said above, 6 times is just a transgression. Tread cautiously.

Get to know him. Away from your home and your son, at first.

You will know soon enough, if it is in your best interests to pursue, or reconsider?

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A male reader, Jadakiss87 United Kingdom +, writes (5 October 2013):

It's interesting to read that you just wrote to him one day?

How long have you been in contact with him? How many times have you visited?

Il be honest with you right now, if my little sister who is about your age was planning on starting something with an ex convict I would be hugely stressed, especially with your history and what you've done to get your child back and build a life for the two of you!

Please think very carefully about what makes this man in particular stand out as a match for you, your ability to turn your life around through hard work is a testimony to yourself and any man who is lucky enough to have that as part of his partners traits is a lucky man! I guarantee you there are many men who are probably better equipped who would give an arm and leg for someone like you. Please don't just settle for him because you don't want to be alone.

If you truly do want to try with this man then going forward with him, I wouldn't let him into your life fully for a long time, let him earn your trust for one, and your respect second, if he comes out and can get into work quickly, put a roof over his own head and seems like he has sorted his life out then I would consider telling him your past. Please don't rush things and don't try to fix/save him by putting a roof over his head or provide for him. Your child is the one you need to think of the most here.

Good luck

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A female reader, Tisha-1 United States +, writes (5 October 2013):

Tisha-1 agony auntAnd to go on that last post from you, I guess you could say that you are also well-behaved and don't cause problems. You have been checked and at the moment have no detectable diseases.

You also have fought for getting your child back, found a job, have managed to get a car, and feel stable.

How old is this man who was caught, tried and convicted for a crime he committed at the age of 17?

I'm still going with being honest.

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A female reader, Tisha-1 United States +, writes (5 October 2013):

Tisha-1 agony auntYou wrote him one day because…..

your friends said he was well-behaved and didn't cause problems?

Why does that sound like an ad for a rescue dog?

Why did you choose to write to him and want to start a relationship with him?

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A reader, anonymous, writes (5 October 2013):

This is verified as being by the original poster of the question

I wrote him one day, and eventually got to go visit him. Alot of my friends work at the prison he is in. They say he is well behaved and doesnt cause problems. I know everyone has their opinion on what a good man is, but if I didnt believe he has changed, I wouldnt waste my time :) I am STD free and plan to make him get tested too. :)

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A female reader, like I see it United States +, writes (5 October 2013):

like I see it agony auntFirst off I want to congratulate you for cleaning up your life the way you have. You should be proud of your present, not ashamed of your past. To live though hardship and yet recover from bad choices takes a lot more character than a spotless past on someone who has skated through life without ever really experiencing its troubles.

If I am being honest with you, sweetie, my concern here is not whether you (past and all) are good enough for this man, but whether he is good enough for YOU. He's coming straight out of prison and while you don't say how long he has been in for, chances are that regaining his freedom will be a major adjustment for him. I've worked closely with current and former inmates over the course of my current job and it seems like one of two things happen. Either they emerge from prison having realized their mistakes, cleaned up their acts, and vowed never to take that path again, or they emerge the same person they were upon incarceration... except older, more bitter towards the system, and with more "street smarts" and tricks up their sleeves than they had going in. These are the ones who have not learned their "lesson," if you will, and who are likely to end up back in jail within a few years.

I hope for your sake that this guy falls into the former category, but until you have really gotten to know him in person and know that he has cleaned up his act, I would tread very, very carefully, especially since you've worked so hard to build a safe and responsible life for yourself and your son. Please, please take the same precautions with your first few meetings with him as you would when meeting a stranger off the Internet... make sure you meet him in a public place during daylight hours. Tell someone where you are going and when to expect you back. Don't introduce this guy to your son until you know he is someone you can trust.

A note regarding the STD testing: make sure HE's clean too. Depending on the prison, injectable drugs and risky sex practices are not out of the ordinary, and it's not like inmates have the freedom to go buy condoms or new sterile syringes whenever they want. You know you are clean, so don't play Russian roulette with your health by assuming this guy didn't catch anything nasty while he was incarcerated.

If you take only one thing from this post: please make sure this guy is safe and *worth* letting into your life before you worry about how best to let him in Good luck and best wishes :)

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A reader, anonymous, writes (5 October 2013):

My vote is for letting the past stay there.

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A female reader, Tisha-1 United States +, writes (5 October 2013):

Tisha-1 agony auntHow did you meet him, by the way?

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A female reader, Tisha-1 United States +, writes (5 October 2013):

Tisha-1 agony auntI think being honest and brave is the best way to be.

If he can't deal with your reality then he's not the guy for you. He's not exactly a poster child for "perfect human being."

You had a rough start. You had a rough middle. Are you back in control of you?

You now have a child, a job, a car, and stability. Sounds to me you are back in control of you.

So you will probably have a very good life from now on, because you are back in charge of it. Why would you let these insecurities take over? You have moved ON, girl.

Be honest. The guy that shows up to be your match will be awesome.

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A reader, anonymous, writes (5 October 2013):

If he was in jail and served time, who would he be to judge you? You apparently don't know each other well.

He wouldn't have served time; unless he had prior offenses that compounded burglary. Juveniles get off with a slap on wrist for first offenses. So don't worry.

You got your child back, beat addiction, and turned your life around. You're an inspiration to troubled youth. You have no reason for shame, and if he can't deal with your past, he'd be a hypocrite. Let no one judge you for your past. It's the present that matters.

I think you might be putting your hard work in jeopardy; if child services finds out you're spending your time with a recently released convict.

He will likely be out of work for a while, so you may end up having to stretch your already limited budget three ways. The stress will get to you, and he will be as dependent on you, as your child. Who is the top choice above any other human being in your life.

I hope he isn't expecting for you to support him, or provide him shelter. It is likely you are receiving assistance, and you could lose benefits. So please be careful.

Guys recently released after serving time are a handful.

They are paranoid, temperamental, and can be overly aggressive. They aren't the greatest people to have around young children. You are no stranger to the system.

Letters don't reflect the man behind them. Women are taken in by these charming inmates, and end up in a lot of trouble. You aren't his savior and won't necessarily turn his life around. That's up to him. He's just looking for a place to land when he gets out. Single lonely females are always first choice. They usually have low self-esteem and a Florence Nightingale complex. They believe they can save lost men; and they're undeserving and unattractive to anything better. I hope this isn't you.

He can hide a lot under a phony exterior, and his true nature comes out when you piss him off; or he is under the influence of drugs and/or alcohol. Keep your eyes open for red-flags.

Your current life,is in no comparison; in spite of your past troubles. If you served time, you wouldn't have earned your child back. That means you worked your tail off.

You have a child to worry about; and you may be heading for disaster. Your life has been tough, and you couldn't have chosen the worst of prospects. It's your choice to make, but your child also depends on your better judgment. Child services will not think twice at the first sign of trouble.

As you know. You're taking on a huge responsibility. So I am going to address that for your sake, and for the kid.

He'll be jobless, possibly on probation, homeless, and he'll be expecting you to take him in; if he has no where to go.

You're so young, and life dealt you so many obstacles in your life. Your child deserves better than being in and out of the system. I'm sure that's what you've known throughout your own life.

You've already opened the invitation. Most likely you've formed an emotional attachment, but your post is far off track. His judgement of your past is far from important.

Your staying on course and taking care of your child is the priority here.

A guy who just got out of jail, is the last thing you need in your life. You're really a good girl, that was dealt a lot of crap in her life.

If this advice means anything at all, put you and your child first; and keep him out.

My heart sinks; because I know how this usually turns out.

My best hopes for you and your kid all the same.

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A male reader, no nonsense Aidan United Kingdom +, writes (4 October 2013):

Tread carefully.

Of course the man can’t be condemned forever if he’s genuinely sorry for what he’s done, you turned things around and maybe he will too (although it’ll not be easy). He’s just about to be released following a sentence for burglary, does he now firmly reject criminality? Whatever you do, however much you think of some-one think carefully about whether their presence in your life threatens the stability you have created for you and your child.

If you think telling about any aspect of your past puts you or your boy in danger, then of course don’t.

Otherwise, you don’t have to. It depends on whether you will feel like you’re holding something back from him and that will stop you being fully able to participate in this friendship or relationship. IF you’ll be consumed by guilt that you’re hiding stuff, tell him.

You do have the luxury of time though: you’ve created a stable environment now for you and your child, and by the way fair play to you for doing that. You need to introduce him in to your life and your son’s slowly, so if you’re not sure, hold back until you reach a decision. Judging from your post, the way you’ve written it, and the turmoil you’re in, my judgement is that you’ll have to come clean about your past in the end if things get serious.

One other reason why you could have to tell him something if you had a relationship, is if you have any kind of sexually transmitted infection. That’s not nice to say but there’s no getting away from the fact your past lifestyle was risky. It’s worth both partners being tested when they start a new relationship anyway, whatever your past. Again though, the fact that you have had previous partners does not mean you have to tell him that some of those were paying for sex.

The point you need to take away, is that what you reveal from your past is up to you, and when. If you do come clean about everything (and I think you would have to if this actually became serious), if he’s worthy of you he’ll understand: the past is the past. He already knows you had a child taken away and drugs were involved so he knows you’re no saint and neither is he, and that’s not put him off. You’ve changed your life now, so focus less on feeling ashamed at what you’ve done before and more on being proud of what you are doing now.

I wish you all the very best.

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A female reader, llifton United States +, writes (4 October 2013):

llifton agony auntSounds to me like he has no room to judge, seeing as how he's in prison for his bad decision-making early in life, too.

You don't have to tell him if you don't choose to. That's up to you. But that usually all comes with time and getting to know someone. no need to just dump it all out there right away. Take your time and get to know each other slowly. And when you're ready, tell him then.

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A reader, anonymous, writes (4 October 2013):

This is verified as being by the original poster of the question

I would lile to add, I am std free. I got tested two months ago.

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A female reader, Aunty Babbit United Kingdom +, writes (4 October 2013):

Aunty Babbit agony auntIf you two are going to make a go of a relationship then you must be honest, about everything.

If you don't tell him and he finds out somehow, he'll wonder what else you've withheld and the relationship could falter.

If he can't handle it and judges you (and let's be honest, he's just got out of prison so he's in no position to judge you)then he's not the right guy for you or to be around your little boy.

Ok, so you've done some stuff that your ashamed of, you made amends, my darling, you straightened your life out, fought for your child and got him back.

Well done you, be proud of what you've achieved and who you are today, stop dwelling on the past.

I know you want to find love but don't feel your worthy of happiness, but you are worthy of love and happiness.

Please though, do not settle for any man (regardless of background) who will not accept your past, your child or who you are now. If any guy treats you badly, bullies you, hits you, condemns you for your past or is in any way unkind, get out straight away because that is not love.

Be brave and be proud of who you are today.

I hope things go well.

I hope this helps AB x

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A male reader, CMMP United States +, writes (4 October 2013):

Make sure you have been tested for STDs, you owe him that, but nothing else. He can fall for who you are, not what you've been through. Don't lie, but don't bring it up either. As your relationship progresses you can choose whether or not you tell him, but you shouldn't ever feel like you have to.

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