At almost 48 I assume I count as a senior here.
I can't tell you if the feeling of wanting to connect ever goes away because I've never wanted it to go away. I do all I can to be loved and give love to my partner, kids and friends. The other two questions are a bit obscure, so I'm not sure where to go with them.
What I don't understand from your post is what you WANT your life to be. Do you want to be alone? Or do you want to open yourself back up to the possibility of love? And why did you choose to train yourself to be unfeeling in the first place?
Do you have any diagnosis which would impact your interaction with others? Eg; Aspergers, anxiety, depression?
Never regret anything that has happened in your life. It cannot be changed, forgotten or undone. So, take it as a lesson learned and move on.