Good for you for trying. I hope you're able to reconnect and if you don't, you can at least rest assured that you've come a long way since you were first friends.

I've lost a handful of friends over the years. The one that makes me the saddest is a friend that I lost in 2006. We'd known each other a few years when I helped her through a pretty difficult divorce. At the time, she was living in Denver, having moved there with her then-husband in 2005. When she moved back to Indy in January of 2006, things were fine at first, but she soon started to seem rather distant to me. She wouldn't return calls and when I would talk to her or see her, it was if there was an elephant in the room. Something was just not right.

At one point, I asked her if anything between us was wrong and she assured me that it wasn't. From there, we started to talk less and less. I was in the middle of my own difficult relationship and breakup at that time and, in I was just so hurt all the way around, that I eventually let the friendship just expire. Not that she was putting up any kind of a fight about it.

It pains me that I never pressed her to discuss what was going on with us. We never exchanged a harsh word and never openly had any kind of disagreement, so for the friendship to just die on the vine seemed so weird.
I've known several people in my life like my former friend. They're incredibly charismatic and are used to having people sort of falling at their feet to be their friend. I was one of those people. They're not very good at reciprocating the friendship though, at least unless they're getting something at the moment from you. That's sort of what I suspect happened. When she returned from Denver, she started hanging out with a group of coworkers who were very social and "fun." She needed that. What she apparently didn't need any more was a shoulder to cry on. At least that's my hunch.

But I miss her. She and I have both married since then, and it pains me that we've both moved onto really happy things without the other sharing a bit in it. I've never given any serious thouight to reconnecting. For me, it's just been better to move on.