I've had female friends and everything, but I probably end up with a combination of my own fear and what I'm looking for shooting me in the foot, to the point that I am in the same boat, never kissed a woman even, though I could probably say I've been on what could be considered 2 or 3 dates.
I really don't want to just "start" a relationship with someone; I want to have some sort of connection with a girl before asking her out. Just straight up asking out someone you barely know seems really strange to me. Of course, then, what usually happens is that I end up waiting too long and some other factor steps in to prevent any relationship past friendship starting. Most often, I just get comfortable in the platonic friendship or I just wuss out on asking her out. If I do manage to gather the courage, it's then that I find out most of the time that she has some mysterious "boyfriend" I've never met or heard about until now, or else she makes up some other excuse. This has led me to add on another factor to my fear and make me more likely to wuss out on girls later; the feeling that I am undesirable. That the answer will always be "no", and that I am always the problem. This destroys my confidence, which makes her less likely to say "yes" if I do actually ask her out. 'Tis a vicious cycle, but I have vowed that if I am not going into the religious life, I would not live my life alone.
Though I think in the past there have been 2 or 3 girls that actually liked me, that I didn't pick up on until it was too late. In fact, I have a story of EPIC failure to pick up on it with one of them from back in high school, that I mentally kick myself for to this day.
