chuckles
First, stop. Relax. You sound like your waltzing towards the very thin line of obcession. Let's nip that one in the bud so your community doesn't wake up and find you on the front page of the local paper as a stalker.
Second, life is imperfect. Don't think that there is a set protocol for doing stuff like this. If there was, someone would have already written a book and lived off the money made from it a long time ago. That's why it's so hard, there isn't any one way. Life is random, you're going to have to ad lib it.
One thing to remind yourself is that what you want to do -really isn't that weird-. I know I used to do that all the time, worry that I was being weird or strange. You're not. People call other people up all the fracking time. Indeed, it's actually as easy as saying, "Hey, I haven't seen you in awhile. Insert Optional Small Talk Care to hang out/see a movie/go to a concert/get a bite to eat?"
It's seriously that simple.
I grant you, my suggestion is a bit of a cavalier way of answering your question. So a few other tips.
Going out on a limb, I'd like to say I think perhaps the most important thing is your mindset. Fixating all your hopes and expectations on one thing isn't healthy... it's akin to betting your happiness on a coin toss. Life is something no priest or wiseman can explain to you, nor is it something that a teacher or parent can tell you exactly how to live. Life just is, and all we can do is accept it, and then live it. If all goes well, then what a wonderful life it is indeed, if not... that's how it is and all you can do is to try and make the best of what's to come.
Ganbatte... To health of the heart, and fortune of the soul.