How do I respond to this friendship?

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I have a dilema that has been bothering me for some time. It involves a childhood friend that added me last spring on Facebook. I would like to send a message to this person, but due to the history of the friendship, I am not sure how to respond, or how he will take writing directly to him. Basically, I am afraid of losing the connection if I make the wrong move or say the wrong thing. I know that I shouldn't put too much stock into, but his adding me on Facebook was one of the things that gave me hope and helped me move on from another friendship that went bad.

The background on this friendship is that this person was almost a member of our household during my late elementary/ middle school days. He would spend a lot of time (including sleeping over) at my family's home to escape his homelife, the poverty and the situations that happened there. This arrangement worked out well for a few years, but the situation at his home got so bad that my parents called Social Services on his mother. He was removed from the situation and went to live with his grandparents. In the last 20 years, I have tried to contact him on a number of occasions with mixed results. The times that I have tried to contact him, things go well for awhile, and out of the blue he has tersely told me that we could no longer have a close friendship, we have nothing in common and to quit contacting him. Add to the mix the fact that I have also had a 20 year, on and off again obsession with him, the closeness that we had when we were younger, and how he pulled himself up by the bootstraps to be a somewhat successful person.

Due to how certain dynamics played out this spring, he added me as a friend on Facebook, after being out of contact for over 5 years. It has been one of those Facebook friendships where little has been said to one another. I have commented a couple of times to posts and to wish him a happy birthday. He has never really went out of his way to ask how I am doing or what is going on in my life.

I would like to send him a small message about what is going on in my life and the experiences that I have had over the last couple of years. Due to his career, I think that he would relate to one of the major things that has happened in my life during that time. I am not sure if I should send him a message, or if I should just let it be and "quit while I am ahead"? Any ideas or suggestions?

I see that the couple of people that have responded have went along with how my subconscience mind is telling me to deal with the issue. When I talk to folks at church, the same answer comes out of them. They always say that if something trips his trigger on my Facebook page, he will respond. They have also told me to not push the issue of friendship, and that an opportunity may arise someday, in which it will be a appropriate and comfortable time to converse with one another.

On an impulsive front, I sometimes think that I am looking for accolaides and validation from this person regarding some of the volunteer work and involvement that I have had in my community over the last couple of years. This is probably due to the admiration and obsession that I have had for this person over the years. It may also have to do getting a little bit of acceptance from him due to ways that he has sometimes treated me as well. I also would like to prove to him that I am a much better and different person from the last time that we interacted with one another. I have a better handle on his personality, his personal dynamics and the issues that he deals with. It has been a relationship where I have always thought that the next time we interact will be different. The more I think about it, the more complex of an issue that this really is.

You've given yourself some pretty good advice.