Well, don't get frustrated. Based off of the fact that you said you take rejection well and that you seem to approach women like you would a test, that makes me think you're falling into the same problem I had for quite some time - trying too hard. I used to think that if I tried harder next time some girl I was interested in would like me. Before I knew it, I was trying too hard and coming on too strong and really just taking blows to my confidence. Now, I just talk to a girl with confidence and it turns up like this - either she and I end up being interested in each other or we end up becoming friends. Worst case scenario is we become friends. Not bad if you think about it really - I always approach it like I have nothing to lose and everything to gain.
I'll give you an example - just today I introduced myself to a girl I had class with a couple years ago that I had actually been wanting to talk to for some time but I never had the confidence to talk to her until recently. So, we happened to be next to each other in line at this little cafe' and all I did was ask her if we were in class together. I pretty much opened a faucet, as she was talking my head off before I knew it, and I found the opportunity to introduce myself to her and learn a little bit about her and let her learn about me. All in all it was a pretty good first impression, and now there's an open door in the future for either to be friends with her or something more. I see it as part of the fun of it - seeing what will develop and which way things might go.
Maybe I do, but I know I don't come on too strong. I'd say the opposite is the problem.
As for the second paragraph, I can only say 'if only'. And there I'm thinking of a specific one. Laconic and reticent are the right words for her. If only the worst cast scenario would be becoming friends. Heck, that would be a pretty good scenario. If I acted in the way you say in your second paragraph I'd get about a one word response, and have her walk away as quickly as possible. No all women respond well to trying to be conversational.
Actually, the only reason I said women and tests in the same breath was because it was mentioned before. They're nothing alike. I put far too little thought into tests for there to be a comparison. I think I studied what, fifteen minutes for my last Classics test? Heh. Ended up with a good mark, though.
Anyway, I actually do tend to have the first inclination to act as you've said. The problem is, in those situations those are usualy women that I'd rather just be friends with, rather than actually go out with. So that all works well in order to be generally friendly with people. It doesn't work so well otherwise, because, well, there are too many factors. Firstly, I'd have to be sure about myself. That's important, because I'm not going to set myself up for something I'm not sure I want to do. Secondly, there are the myriad of factors concerning the woman. I'll admit it, I'm picky, but I have to be. Not just any woman will do - not just if 'I happen to get along with them' or any of that rot. I'm an exceptionally long-term thinker, so I absolutely disdain doing things ephemerally. Just doing things on the fly is rather irritating, as it's not responsible. The thing is, the sort of woman I need isn't just someone I can get along with now ... and that's one of the problems. I'm sure you'll say 'well, you never know who you'll get along with until you try', to which my reply is that 'even if you can get along with someone for now, for a while, or if they're fun, that's being foolish. You need someone whom you can spend your life with.' Not to mention the fact that I really don't like women who are overly cheerful, or silly, which seems to be in the majority. There are few scholar-girls out there, and that is about the only thing that will do for me. Oh, and let's not forget the religious corner, too. I'm devoutly religious, such as 90% of the population isn't, which does pose great trouble in this regard. I'm not one to bow easily on matters of religion, nor am I all to compromising. With friends, yes, it doesn't bother me, but with a woman I'd perhaps marry? It's an issue that I'm not sure how I'd handle. For all this, I cannot simply take it lightly.
You see, most people have a more loose idea of dating, but I've not been raised like that, and I cannot bring myself to think like that no matter what. If I ask someone out, it's someone whom I think I might be able to spend my life with. Impossible to say now, you say? Not as impossible as you might think. And at least I try and be responsible. 90% of the population isn't.
Of course, what you said there is supposing the fact that a girl would have the time to just chat in reply. That's a rare thing. University has this way of scattering people after class, and it's difficult to do during. I'm very serious, so I'd be loath to make an obvious small-talk comment just to start a conversation - I always would need a reason to talk. And that's a rare thing. And even when it bloody well presents itself, not every girl seems willing to be nice enough to give so much as two conversational words in reply. Apparently. Hmph.
I'm just a regular old curmudgeon, eh? Actually, that's the problem, you see? In things like this, I don't act like a kid, I don't act like a youth. I act like someone old, resevered and patient. Weighing my own thoughts and feelings and definitely not acting on impulse... well, usually not. And the sort of girl I'd need... she could respect that. For she herself would not be one to act by transient emotion. I'd rather date a recluse than one overly gregarious... they tend to be more interesting. Of course, the more reclusive seeming ones are basically un-attainable, or so I've discovered. Yeah...
Okay, so I'll admit it. I might try too hard, but that is in my bloody character, and without that it wouldn't be me. To suddenly become more gregarious and loose would require changing a very core aspect of who I am, that seriousness which pervades much of my thinking. People have told me I'm not fun. Well, maybe I'm not. Or my ideas of fun aren't what most people think of, and aren't what most girls care for. But I'm not changing. However, I know I don't come on too strong - okay, maybe I have in the past, but I've learned since then.