I need some of your opinions and advice. It may seem silly and trivial but I'm trying to get a read on this guy and I don't know if I should leave it alone or help it along a bit more. I've actually never dated and I'm used to having men make their intentions very well known, which is not the case in this instance. Also, I have read the book "He's just not that into you", and I'm thinking this case may actually qualifiy as that one in ten times that a guy may need some more shoving - or I may have scared him off a bit based on some of our past interactions and am looking for a way to redeem myself. I was just hoping to put these interactions we've had thus far out there and see if anyone thinks I should pursue this one.

He's actually an old boyfriend from high school that I looked up online. (I know that's totally taboo) and to elaborate a bit as to why I felt that was ok - we were both always the type to have lots of friends of both genders, we were friends outside of a relationship, etc. Basically, I just wandered what he was up to these days. I hadn't thought about him for years but something reminded me of him and I just got to wondering. He ended up being single, no kids, etc. We started emailing each other and he mentioned getting together sometime to catch up. We then exchange numbers. He does end up calling twice, on two separate weekends to get together, and I end up chickening out - I guess I still have some attraction for him and I'm a little nervous about it.

Some time passes and we continue to email and finally end up getting together after talking about it via email for a year - (mainly my fault). Everything goes great - it's great to see him and he's still the nice genuine guy he always was. When I leave I tell him to call me. This is where my confusion begins. Weeks go by and he doesn't call. A couple of months go by and we chat via email again - he's already mentioned that the reason he is still single is because he's too shy and in his emails he reminds me that I can always call him too.

I guess I decided that I needed some more expression of interest on his part and because he didn't call after meeting up, I let it go. Several months later he initiates an email - hi, long time-no hear, how r u, etc. I mention getting together and tell him to call me this weekend. He calls Friday evening and asks what I am doing. I tell him I have no plans and ask if he would like to get together. We meet up for a couple of drinks, talk for a couple of hours, he hugs me when I leave and tells me to call him.....

That's it...I know it isn't much to go on. I do know for a fact that he is shy - he was in high school too. But he also pursued me in high school. I also did blow him off the first two times he attempted to get together, so I may have made him a little gun shy.

The point is, he's a great guy, I'd like to have a friendship, maybe more, with him. I'm not sure at what speed to move ahead. It's already been two years of emailing and it feels like it's lost it's momentum. Do I call since he asked me to? How long do I wait? Or has he made it clear already that he's really just not into me? Do I ask him out now? That just doesn't feel natural to me....What do you guys think is an appropriate course of action.

UGHHH....I see why some people hate dating.