Before I get into the issue of this topic, keep in mind, I'm a 25 year old guy, that has zero experience with dating (all aspects of it...), not to mention, I'm socially awkward, and pretty reserved, and really don't have a social life, period. I've only ever really "liked" two girls, and both rejected me, I took it very hard both times, and both resulted in me making a giant fool out of myself, which lead to the girls in question both hating me, and me feeling even worse because of it (honestly, I'm still pretty hung up on the last girl I liked, and that was nearly two years ago...).
So, a few months ago, I crossed paths with this girl that goes to the same school as me. We're not in the same classes, but it's fairly common for us to see each other around campus. I kinda got the sense early on that she might have a thing for me, but I really can't tell (and I'm not much in the mood to gamble, after having made such a mess of things in the past). She talks to me almost every time she sees me. Sometimes it's just a simple "hi", other times it feels like she's trying to make conversation. Then again, from what I've seen, she seems pretty friendly with everyone, even other guys she has class with. So I don't know.
Thing is, I'm in a really... "weird" sort of place, mentally, because a lot of different factors... Such as:
1. I'm lonely, I'm starved for affection and intimacy, and here's a nice, sweet girl that *might* potentially have an interest in me.
2. At the same time, I still really want the girl I last had a thing for two years ago (or at least, someone exactly like her), and this girl at school is only "okay", in my mind, in comparison.
3. After a few interactions with this girl, I looked her up on Facebook, and basically tried to find things that would be turnoffs to me. Being a bit of a "nitpicker", that wasn't too difficult for me. Most notably, I noticed that the city she lives in is about 30-40 minutes away from me.
4. Yet, as much as I keep trying to talk myself out of having any interest in this girl, I find the possibility of her liking me to be peculiar, and I like the attention I get from her (and at the same time, when she's being friendly with other guys, I feel a slight tinge of jealousy).
5. But, even if I wanted to pursue her, I don't know how to do any of that. I can barely have a conversation, let alone flirt, ask a girl out, plan out dates, etc. I don't even know where I would take a girl on a date.
6. If I ask her out and I'm wrong about her liking me, chances are, things will become awkward at school. Granted, I graduate in a couple of months, but I just don't want to make that time unpleasant for either of us...
So, I don't really know what to do. Part of me wants so badly to date and have a girlfriend, but another part of me has these lofty ideals about dating and romance that most people will probably never live up to, and then another part of me is so naive and childlike that I don't even HOW to date a girl, and of course, another part of me is terrified that I'm going to make a big awkward mess with someone all over again.
Yeah, as you can clearly see, I overthink things quite a bit. But, that's kind of who I am... I'm a neurotic dope with some nagging anxiety issues. What can I say...?
I dunno. Any input?