Each time I allow myself to feel connected, love, empathy, I make it that much harder to let go and follow what it is I need to do or want to do. But in order not to feel, or as an indictaor of not being able to feel and express that feeling freely, I cannot stay involved, not in the minutia anyway. I need lots of space from any given idea in order to see it properly. In order for it to have a porper place within my life. No one thing can take over lest it cloud and colour everything else. Caring for someone doesn't involve becoming attached to them, and yet without that attachment, can there be true caring? Without feeling their pain, their love, their joy, can there be real empathy? For me, when I feel myself start to feel love and care for someone, i'm on the road to attachment, because once i've given all I can for them, or all I feel i'm able to give, letting go becomes a problem because there is a certain expectation from them that I cannot control. So what was something given unconditionally and meant to be received without expectation of it continuing, when it stops being there, the hole it leaves is noticed quickly, and something rushes in to fill it. They can instinctively do what they feel will maintain it, and so we now have a kind of power struggle. Me, feeling like I have to pull away, they feeling like they have to pull me back, creating quite a resistance until something gives. I love to love people, help them, offer advice when relevant, and do, but have to accept that if I do, or do it too much, there will be a price to pay, that they will either expect it and look for it, or get hurt and change the way they feel about me as a result. It's not consciously chosen, but each little moment of feeling and judging and deciding what happens within, creates little changes, nudges, towards what will ultimately be what is felt.
I think acceptance and saying yes to the situation of not being able to control ones expectations could help a great deal....not sure if you tried this yet though. "He who trims himself to suit everyone will soon whittle himself away."
what was once acceptable ..... is no longer..... as it has not adapted to what has become..... some connections grow and grow as time moves on and details change others drift apart over time as different directions are desired..... if we look around us we can find the most extreme of these everywhere and everything between and beyond as well.... time takes all things and makes them into others..... even if we sit back and try to deny its passage.... still on it flows.... and as each flow along their own track..... there are those we travel near for a time.... and those we only just pass by.... each has its own effect on what we are becoming along the way.... even the ones we never liked....
I too have trouble letting go, and yes the hole can be daunting to fill up. I struggle with letting go of a lover, while they break free i am a caged bird without the song. But Buddha teaches that expectation always lead to suffering, because when we don't have what we expected, our hearts become jaded. So how so we let go? I don't know really but what I do know is that by living for yourself and/or for God, we relinquish all feelings of external connections, and only then can you ever begin to let go.