When we were kids the guy had a crush on me. I was 17 he was 14. I moved away but my younger sister stayed. Some time later these two had sex. She was 16 he was 18. I never knew this and over the years as I visited home I would see him on occasion, however he was married or I was married and neither of us was anything other than polite. However recently he contacted me. It's been 22 years since I left home and he ended up telling me he still has this crush on me he is free now and would like to see if we hv a connection. I'm interested so we start talking, texting making plans to meet. When I bring this up to my sister she tells me she slept with hi and continues to explain. That in his youth he slept with many girls and was basically a player. I am shocked but when I find out this 1 encounter happened when she was 16, I don't think it's that big a deal and I also explain that so far he has treated me with nothing but respect and as far as h player status in the past it doesn't bother me... What 16.17.18.19 year old boy is not a horn dog... However my sister want drop it and keeps calling me dumb, saying I'm setting myself up for failure etc but emphasizes that she is not jealous she is looking out for me... I asked I asked him about it. He didn't remit first or choose not to remember. Then admitted it but said it was an indiscretion of youth but that he would like to see if there is a change of a relationship with me.what do you think I should do. Oh since all this started he and I did have sex... It was protected and great by the way.. I never mentioned this to my sister but ever so often she asks me questions and makes mean commits. What should I do? Family does come first.. right?

Sounds more that she is jealous, since to be honest as a older mature person, almost any man you will date will have had sex with a number of people, and most of them will be widowed or divorce and most will have had many relationships and broken up

You were married ? So I assume you are divorced now ?
So his family could think you were setting him up for a bad relatoinship since you have a history of divorce.

And to be honest most 16 to 20 year old teen boys have a bad history of chasing girls, and often this is far out of their system when they are older.

Only your sister knows what the issue is, but it is her problem not yours, and she needs to get over it, and understand she can not run your life

Thanks Fr_Chuck, I was am starting to feel the same way, that it is jealousy. She has not been married, no kids and here I am relatively fresh out of a marriage and have someone that is showing a lot of attention... New problem though, she comes to me and tells me not only did they sleep together the one time, but she became pregnant due to it, but ended up having an abortion. Now it seems like she is broken up about that in the sense that now in her late 30's she has no kids; but in addition to all this apparently she went to "this guy" and told him that she was pregnant. He in turn said o.k. then I have to do what's right, we will keep it... She then told the "the guy" she was kidding, because I am assuming at 16 that was not the answer she was expecting, she went on her way and fond a way to take care of the preganancy. So this throws a new wrench into the scenario. I understand why she is upset, but I still don't see that I should not try to have a relationship with this man. "Now"... I don't know if that makes me sound bad or what... But I don't think it's far for me to have to deny something that seems very right, we have so much in common and have went through many similar trials and tribulations. On the one hand I think I will just continue to see him and not say anything to her about it, and just see where it goes and on the other hand does this make me seem desprate for a man..

Yes, family comes first, but this doesn't have anything to do with your family. Just because your sister got banged by some guy when she was 16 doesn't mean anything. He could have changed his ways, and so many years from then, I would expect that he has. Also, she doesn't know the guy as she used to and if you see potential for something go for it, she is going to have to respect your decision as an adult woman who like a male, and if it bothers you you can even tell her to mind her own business and let you make your own personal sexual decisions.

I feel for your sister. This may not sit well with her. Keep it to yourself. Why does it have to be discussed until you know the relationship is going somewhere.

Personally I would not get into a relationship with a person my sister had one with, especially with that history.
Keep it to yourself. If you see you two may have something, then you deal with your sister. Until them, there is no reason for her to know.