What is it that makes Dating so Difficult?

I have been learning more about dating in its various forms this year.  The idea of selecting someone who you want to spend the rest of your life with, out of a pool of strangers, is still unfathomable to me.  I am not very good at deliberately starting relationships of any sort, although I am a little better at further developing the ones that I have managed to stumble into.  But the process of someone going from being a stranger to...well: not-a-stranger, is something I have trouble with. 

If we combine this with the pressure or expectations that the idea of "dating" usually entails, the whole process does not seem appealing in the slightest.  I don't know exactly how to describe the element that "dating" adds to the equation, beyond just getting to know each other, but it definitely adds a different factor.

This was made especially clear by a situation in reverse last week.  I went on a "date" (depending on how broad you want to use that term) out to dinner with a girl last week.  Technically I asked her to dinner, but only after she made it pretty clear that she was open to the idea. (I usually miss some of those subtle cues, but she didn't leave much doubt, albeit in a fairly slick and graceful way.)  I almost felt conned into doing it as she walked away, if it wasn't for the fact that I found her attractive.  Then the question arises, how should this be handled?  What does "going to dinner together" really mean to her?

It came out later, while we were working out the logistics of when and where, that she has a boyfriend.  And one she moved to out California four years ago to be with, which I am going to interpret as a serious relationship.  I guess that answers the previous question: "not much."  So we met for dinner, and we talked about all sorts of things, and it was actually quite fun.  I didn't feel any pressure, and wasn't wondering how she felt about what was happening.  When we were done, I walked her to her car: big hug, with an excited reference to next time.  Pretty much like when I go to dinner with one of my close friends, but she was practically a stranger.  I guess this is how you "make friends" and I am just unversed in the practice.

At the end of the day, when I end up going on a "real" date (whatever that is) I wouldn't mind it going exactly like that, except with a girl who was actually available.  But if she was available, I don't think I would have been able to relax and enjoy myself.  Why is that?  The only real differences would be entirely in my head.  Previously I would have written off the potential difference in my perspective to the fact that she was basically a stranger.  But in this case I was fine, so clearly that's not the issue.  Whatever that difference is, I am going to need to figure out how to get over it.

One possibility, which I will examine next time, is that it may be rooted in the "spirit of rejection," and the ways in which that has manifested itself in my life over the last 15 years.  But I am only just beginning to learn about what that means, and the other spiritual aspects that affect our relationships with others.