Hi guys,
I am a 22 years old virgin, and I feel like it's a big part of my life.
I've been told by my friends that I'm good looking, that I have a good personality, that I have a good job and interesting life, and that I'm not shy with the people I already know. The list goes on, yet the fact that I never had a girlfriend (or anything even remotely close to that) is a real burden.
I have a habit of falling in loves with my friends (most of whom I had work relationships with). I find a really nice girl, start talking to her, and soon after I'm deep within the friends-zone, I have numerous attempts of me trying to break this barrier, but to no success so far - either they ignored the signs, rejected me really nicely after I gently told them, or stopped talking to be altogether.
It expresses itself in all sort of ways: I can sit in the train or bus next to an attractive woman, and think to myself how I'm going to do it this time - talk to her and get a conversation starting. But then something stops in my head and I keep thinking about what will happen if she won't won't to talk, or if she doesn't find me as attractive and just walk away. I am so afraid of being rejected again (because that's all I know so far, and it really sucks), that I end up not doing anything.
More recently, I have a really nice girl that I like, who finally doesn't really work near me. When she was in my workplace a week back, I promised I'll find something you can only get from where I work at, and once I found it I told her. I told her (via Facebook) I'll be around her workplace Sunday evening (we work on Sundays), and that I can hop by her workplace and give her that something. She proceeded to ask whether or not I'll be in a popular hangout place near her work. I said yes (and made up a story about me hanging out with my friends there) and she said that she'll be me there (luckily, I found some friends willing to go there with me). The conversation (on Facebook) went quite smoothly, and I really didn't think there was anything wrong with it - I even got her phone number so that we can find each other.
Last night I went to sleep, and started thinking about it, and somehow I convinced myself that she isn't really into me - that she was just being nice to me - and that asking her out on a date on Sunday will result in a definite refusal.
It is a never ending cycle of me liking someone, then either getting into their friends-zone, being too afraid to ask them out, or both. How do I get out of it (and specifically, asking the girl out on Sunday with a high change of acceptance?)