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At what point in a relationship do you reveal your past?

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Question - (20 November 2008) 15 Answers - (Newest, 5 December 2008)
A female United States age 36-40, anonymous writes:

At what point in a relationship do you reveal your past? I'm 20 yrs. old and this is really my first attempt at a serious relationship. I was a troubled teen. I used drugs and alcohol. I became sexually active at 14 and had literally dozens of partners. I lived from place to place. I didn't care about anything or anyone, especially myself.

Now I'm trying to turn my life around. I've met a decent man but he knows nothing of my past. We aren't sexually involved yet. I had to get myself tested for std's because I didn't always practice safe sex during those years. Sometimes condoms were used but if the guy didn't have one, or didn't want to use one, I would let them do me anyway. Thankfully the tests came back ok.

I don't live in a large metropolitan area, so lot of people in my town know of my past. The decent guys won't approach me because of my past. I'm still viewed as the town whore. I know I need to reveal my past to him before things get to the next level but I just don't know how to approach this. I desperately do not want to scare him off. I am already in love with this man. Any advice on how to handle this situation will be appreciated. Should I gradually reveal myself or hit him all at once with it? I'm scared to death he's going to find out from someone else. I hope I haven't ruined my chance at happiness.

View related questions: condom, drugs, std

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A female reader, anonymous, writes (5 December 2008):

Again, thanks for all the advice. I did tell him everything. He took it better than I thought he would. He didn't seem overly concerned about my wild past but he did want to know the number of partners and was visibly bothered by the answer I gave him. Truth be told, I am bothered by it. I've had over 50 partners. I tried to communicate that I'm not that person anymore and need the stability of a normal relationship. I did everything short of pleading with him to give me a chance. So far he hasn't left and I don't feel like he is treating me any differently.

I felt comfortable enough to start sleeping with him, which is wonderful by the way! I do still feel nervous that this will become an issue later. I worry that I will not be good enough for him to stay with long term. With this baggage, I will probably have to worry about that with any relationship I ever have. I wish I had been smart enough to realize your past can come back to haunt you. If I could only turn back time. Anyway, thank you again for all the kind words and advice.

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A reader, anonymous, writes (22 November 2008):

I was just pointed to this question by a good friend on this board, so I hope that I can give you some advice that might help before you break the news. I haven’t read most of the answers yet, so I apologize if I am repeating some things that have already been said. I went through this situation with my wife, with me being the recipient of the information. Every guy is different, so there is no way to know how he will react. I believe that the way the man was brought up in his youth will greatly determine how he takes this information.

My wife and I were 34 years old when we started dating. We had both been previously married to our only sexual partners. She had been divorced for 3 years before we started dating and had 10 sexual partners. She slept with all of them on the first date or the night that she met them at a bar or a club. She felt guilty about how she had behaved and perhaps a little ashamed, as she had never acted that way and never really wanted to. She started to hint to me about the things she had done. She did this with ever increasingly bad sounding hints for a few weeks. Finally she came out with a hint about spreading it all over town and I asked her how many guys she had slept with. She immediately started to go down the list one by one, including some details. I tried to ignore the hints at first, but they became too “slutty” sounding and I couldn’t ignore them any more. She wanted to tell me, but didn’t have the courage to do it. She had trouble because she was afraid of me leaving her and she tried to hide her true feelings about her behavior. I was the first guy who she had a need to tell. I never asked any of the 5 women who I had sex with in my life, but 3 of them wanted to tell me anyway.

I would normally say to not say anything if the guy doesn’t seem to care, but in your case I think it would be best to tell him. My wife and I lived in a small city of about 100,000 people and I didn’t know any of the guys who she had slept with. Even with that, I saw 2 of the guys in the first year that we dated. It was obvious that they knew her and she told me which of the guys they were. It appears that you live in a smaller city or town, so it is likely that he will find out about some of them in the future.

You mentioned about telling him a piece at a time. I personally think that this is a bad idea. He will always wonder when the next bit of information is going to come out and might even have trouble believing you when you tell him that you have finally told him the entire story. I think it would be best to tell him the entire story at one time. Skip the details if you can. A couple of men who have come on the board asking help for their feelings had a lot of trouble getting told in bits and pieces and never knew if they had really heard the entire story. Some guys who can’t handle the number of men are not bothered by the details and some are greatly bothered by the details. I am one of those who isn’t bothered by the details, like the one boyfriend with the large penis or the one who used about a dozen positions. Some guys have trouble imagining their girlfriend getting screwed like this or that, so it is best to leave those details out if possible.

My wife made 2 other mistakes and I made one mistake. She tried to hide her guilt both from me and from herself and made herself sound proud of the way she had acted. If she had talked to me and had shown her real feelings then I would have very likely taken the information better. I made the mistake of being judgmental of her behavior, which made her make the mistake of telling me to never talk about it again. I held it inside me for a couple of years, until I mostly accepted her as she was. I thought of leaving her several times, but never did. I did date other women for a couple of years. She knew this and actually encouraged me to do so. By the way, she was my first after my divorce from my first wife. A lot of men who ask this question on this board have left their partners because they could not stop thinking about her past. I had trouble not thinking about it for the first couple of years we were together. We have been together for over 29 years now.

Don’t try to sound proud of what you have done, as I think it will make it harder for the guy, assuming that he is bothered by it at all. Some men are not bothered by what their partners have done, some hide it and some are open about being bothered. Look at it from a woman’s point of view. Let’s say a guy beat his first wife many years ago. He finally got up the courage and sense to realize what he had done and found help for his problem. Let’s also say that he did completely change and has become a very loving, caring and gentle man. Now he meets a really great women. He has to tell her. He is ashamed of how he acted in the past and shows that shame when he tells her of his past. However, he could also try to hide his shame of his past and in the process sound proud of what he had done. As a woman, which would you be more inclined to try to stay with, the guy who is ashamed and repentant or the one who sounds proud? The cases are different, as you never hurt anyone but yourself, but the idea is the same.

My thoughts of my wife’s past came back last year and it bothered me greatly. I’m not completely sure why it came back after 28 years, but it did. This time she was willing to talk as much as possible about it. The feelings that I had hidden took several months to resolve, but my wife was very willing to help as much as possible. One of the reasons that I was finally able to feel much better about her is that she finally told me her true feelings about herself back then. She still wished that she had acted differently many years ago, but she was so proud of the faithful and caring partner and wife that she had been for the past 28 years that she was able to talk about her true feelings at that hurtful time after she left her first husband and about how she felt about her behavior. The real and true story made all the difference in the world as to how I now feel about it. I still wish that she had not been so easy in those 3 years, especially the first of them and so does she, but now I have sympathy for what she had to go through to feel attractive, desirable and not be very lonely. Her honesty about her feelings is what made me be able to accept that time in her life.

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A female reader, Oblivia Sweden +, writes (21 November 2008):

Oblivia agony auntSo you made up your mind. That's good. At least you won't have to worry about it anymore once you're done telling him. Don't worry too much, you are a good person and your past doesn't change that. I think he knows that.

I wish you luck! Tell us how it goes!

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A female reader, anonymous, writes (21 November 2008):

Thank you to all who answered. I am going to tell him about my history this weekend. I think I will be up front about everything in a general sense but spare him the gory details, unless he wants to know them. I am worried sick about this. I know I need to get this out in the open before I sleep with him because I won't be able to resist him much longer. He's several years older than I am and mature, so I pray that he will give me a chance. Thank you all for the encouragement.

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A male reader, oldfool Australia +, writes (21 November 2008):

oldfool agony auntNo, you should tell him. It is part of laying your heart on the line for him. It means you have opened up completely and are baring your heart to him. If he's a decent guy, he'll accept you for what you are.

Be warned, however, that there is the possibility that he won't accept it. He may reject you. Whether tearfully or violently depends on his character and his disposition. You should always be prepared for this possibility, if for no other reason than to protect yourself.

If you do get a very bad negative reaction, you may have to reconsider what you think of him. It's at times like these that different aspects of a person's character emerge. If he treats you badly, you may come to realise he wasn't as worthy of your love as you thought.

The other possibility is that he will stay with you but feel badly hurt. If that happens, come back and talk to us. Collectively, the aunts and uncles have a LOT of experience advising on negative reactions to a girlfriend's past!

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A female reader, birdynumnums Canada +, writes (21 November 2008):

birdynumnums agony auntIf you value this relationship enough to lay your heart on the line, then I would find a way to tell him the whole and unabridged truth. Any other decision would leave you risking him finding out on his own, which he might view as a betrayal. Frankly, If I were you, I would rather risk the truth that have a thousand regrets if he were to find out from a source Other than yourself. In the very least, if you disclose this to him personally, no matter how difficult this may be, you can choose the words that you use and tell him your truth, which is the most important source of all.

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A male reader, anonymous, writes (20 November 2008):

Ideally the past shouldn't matter, but from a male point of view unfortunately it does for a lot of us. If we begin to care for the woman we would like to make the sex special as the sex is important for many men. If it's really that big you need to tell him, if he finds out later he'll begin to think that all that time he thought was special for both of you that it was only special for him and that he'll look back on the times and never see it the same again, he'd think he made a fool of himself and embarrassed himself.

You need to lay it out before him before he makes the decision so he can accept it and so you both can get on in peace. To say that 'the past is the past' may sound ideal but in reality it does hurt and no words or explanation can change that.

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A reader, anonymous, writes (20 November 2008):

you should never be ashamed of your past.i'm 16 and i got pregnant at 13 and had a baby at 14. i'm not ashamed of that and if u r sure you have no stis then he shud just say it's ok.

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A female reader, Oblivia Sweden +, writes (20 November 2008):

Oblivia agony auntp.s. and if you can, move from that awful place where people view you as a whore! Doesn't sound -decent- to me. I guess the "decent" guys who call you that didn't mind being with you back then?

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A female reader, Oblivia Sweden +, writes (20 November 2008):

Oblivia agony auntI would too say wait till you feel comfortable with him. And you don't have any obligation to tell him about your past life if he doesn't ask you about it. You have taken good precautions when testing for std:s which shows that you are a good person and care about his health as well as your own now. Keep that up and he will know you are a good person whatever others might imply about you.

And if/when he starts asking you about your past, be honest with him but don't act like you are ashamed of yourself. You are not a bad person because of your past, and today you are a good and responsible person, show him that. Don't overdramatize your previous life, you do good as you are.

Be proud of who you are and remember that you deserve a good and decent man!

Good luck!

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A female reader, lotus mama808 United States +, writes (20 November 2008):

lotus mama808 agony auntA person with nothing to hide, hides nothing. I am always very open with my past to individuals who are important to me. I have no pride in what I have done, however, I am aware that without the stupid decisions I made then, I wouldnt be the wonderful person I am today. When I met my husband, I made it clear that I had a very shady past, and I made sure to let him know that I am a wiser, more loyal, trustworthy person today because of it. We all make mistakes, and some of us take longer than others to learn from them, but once we do, we tend to turn out even better than the ones who never made the dumb decisions we did. Don't be ashamed of letting people know that you have learned a lot, and are a fantastic person today at the expense of your past, so long as you truly understand that they were dumb decisions, and you know your self worth. Be honest with him when you feel like the relationship is beginning to enter that deeper level.

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A female reader, vamp-gal United Kingdom +, writes (20 November 2008):

vamp-gal agony auntHey,

You should reveal your past to him whenever you feel comfortable with it. It's your choice, if he really likes you, he will accept who you were and who you've become. Whenever you feel comfortable with telling him, then you should tell him.

Hope this helps.

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A female reader, Emilysanswers United Kingdom +, writes (20 November 2008):

I would wait till it comes up in conversation and when it does tell him that you've done bad things and you are a different person now.

Tell him that you regret everything you done and that you have a reputation round town.

Give him a rough idea that drink drugs and sex were involved. Whether he wants to know the details after that is up to him.

Good Luck!! xx

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A female reader, aphexinfinite United Kingdom +, writes (20 November 2008):

aphexinfinite agony auntwell if i have learned anything is that dont reveal too much because doesnt matter what your past was as long as its not going to be your future. the only reason i would clear the air a little if something was bugging me or i thought someone would reveal me/ honesty is a great thing but it has to be used wisely, even though your turning your life around not all people wil see it that way. if you want or have to tell him anything ask him about his future first. to help you feel more at ease and dont reveal all just reveal that you had relationships and that you ddnt value yourself but you do now sort of thing but i wouldnt admit to have sex so young or that you had sex on a whim.. im not into hiding things or lying but sometimes the truth can ruin it all so becareful.. good luck aphexy xx

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A female reader, penguin64 United Kingdom +, writes (20 November 2008):

penguin64 agony aunttell him briefly what ur past is like. just dont lie or anything and noone can argue. just ask urself would you like him to come clean if his past was like that? but theres nothing sayin you have to tell him....only if e asks

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