Why am I so socially inept?

So, on one hand, I'm so very proud of myself. On the other hand, I am soo completely lost. I think I asked a boy out on a date (at least I thought it was clear it was, but I don't really know if he does). I haven't gone all crazy in front of him yet (unless he's reading this blog---- then I claim the 5th amendment, which says I cannot be incriminated for anything in my blog). Now granted, I've gone crazy in front of some select friends, who I am sure want me to stop discussing the subject. The crazy I refer to is the whole wanting to define something right away and know where I stand (the grayness of life can be confusing and scary sometimes). But on the other hand I've done well in working on my past crazinesses like going all full of despair when I don't hear back from him within a 24 hour period, or crushing so hard that I'm head over heels in a days time period. The other underlying principle in this is that this would be the first time since I started my whole rebirth and reevaluation of life that I started in January that I've actually pursued a boy and I am worried what rejection might do to my psyche (yes, yes, I'm overly dramatic- as I know I'll be sad for a day or two and then move on), but I also think proper development might do wonders for my self-esteem, which has improved greatly. Yet, the weight of six years single still can throw you through a loop.

So the latest is that we might be having lunch again this week. I was kind of hoping for dinner, as it seems more dateish, but other people tell me that lunches can be perfectly acceptable dates. I guess that's the problem when you base your concept of good relationships on romantic comedies where good dates are always at night, had a dinner component, a walk around a major metropolitan area, then a good night's kiss on somebody's front stoop.

So wish me luck as I try to figure out if this boy might actually be interested in me romantically, or just as friends. I am sure there will be plenty of blogs to write about the whole situation. And if the boy is reading this, you could just email me and tell me what you feel :) (again though, I hold the right to deny this)