This discussion should probably be moved to the Dating and Relationships forum; it is well past the Introductions stage.
You're 100% correct. A lot of it is my fear of rejection.
Fwiiw, this is totally normal/usual; most guys have exactly the same issue with meeting women, especially younger and less experienced guys…not that that makes it any easier to overcome the problem.
For example, there were two college girls who were in the same train car as me almost every day and I kept catching them looking at me. One day I sat next to them and chatted them up. I played it slow and didn't ask for their number or anything until the next time we chatted on the train. They gave their numbers, I sent a mail saying something along the lines of "Nice meeting you, have a nice day." or something like that. Nothing too forward. They replied in kind. Then, the next day, they aren't on the train. I didn't see them for a week, so I sent a mail asking how school is going or something of that sort. No reply and I did not see them on the train since. Only saw the cuter one later on at a different time and at that point the jig was LONG over.
Since you posted the story in a little detail, I'll make a couple of comments. Just my 2 cents worth: I think you might have done better if you were *slightly* more aggressive and if you had focused on whichever one of the two appealed to you more or seemed more friendly when you talked to them. More specifically, imo it would have been good to invite one of them to do something very casual, grab a cup of coffee and chat or whatever, in your second or possibly even your first message. They (almost certainly) understood that you were interested in getting to know one of them in some sort of potential dating context, and the very gradual/incremental approach you took (very likely a product of rejection fear, of being afraid that they would flatly turn down your invitation) risks communicating to them a lack of self-confidence or a lack of serious interest on your part. You of course could have invited them both to coffee or whatever, but the longer you wait to signal your interest in one or the other of them, the more awkward it becomes for them. And if they are any more than casual acquaintances, it can become less hassle for them to drop you off their radars than to deal with the awkward feeling of being even mildly in competition for your attention. Anyway, that's my take on your tale, but there is no formula or one right way to meet women or attract their interest. At a slightly deeper level, I'm simply saying that it is helpful to try to see such situations from their perspective and not just your own.
I did not understand your "LONG over" comment. If you were still interested, what was to keep you from approaching her and saying, "Hey, didn't I meet you on the train last X…good to see you again!"?
You're right though. The approach anxiety is just something I've got to get over with otherwise I stand no chance meeting them. They are just two girls out of the hundreds of cute girls I see everyday. It's something I've been doing reading on and working on.
A lot of people have "stage fright" or "performance anxiety", meaning that they get hyper-nervous and even stomach-churningly frightened by the prospect of speaking to or performing for an audience of strangers. The best way to overcome it is to do it a lot…as often as possible, multiple times per week is good; pretty soon you (most people, not everyone) "get over it" and become comfortable with having the spotlight on them, literally or figuratively speaking. Same here, go out and approach women every time there is an opportunity to do so appropriately. Expect to get lots of rejections; you probably will. But after a while you will probably notice that they are totally harmless and stop worrying about them. At that point your batting average will likely go up quite a bit. In a recent post in some thread, @
Solong wrote something like, "You have to be willing to go to bat and strike out a lot if you want to hit some home runs." That is the way to think about rejections imo, as just a normal part of the game, no big deal.
-Ww