I get a bit annoyed when I see people say shit like "not man enough" and that, like, fuck off, not everyone has confidence, speaking as someone that does have confidence (mostly Dutch courage, I'll grant you) I still wish they'd shut up.
This is why I went with "shy" rather than "cowardly."
As for the Dutch courage thing, that has never really worked for me. I am naturally confident about some things and am not scared to voice my opinion but when it comes to women I am naturally shy and no amount of alcohol has ever been able to overcome that. Granted, chatting up strangers in a bar/club has never been high on my list.
That said if the girl is interested she will be patient with you, if not then, well, its just chemistry, I want to say something cheesy like "try a different formula" but I think I've sunk low enough in this thread already.
I have been very good frends with a girl for nearly ten years who I would ('ve) fucked the ever-loving brakes off of, and she felt the same way about me, but there was always strong trepidation of what way that would effect the friendship afterwards. Probably negatively since I had no interest in going into a relationship with her. Small boobs, stupid, cunty friends. eh.
I can admit that there was one of my female friends that this applies to for me. We get on like a house on fire and have been mistaken for boyfriend and girlfriend on a couple of occasions.
Did it make me sad that I never asked her out properly? At the time, yes. Either because I was unable to pull the trigger or because I may have missed out on something great.
However, over time I have some to recognise that she has multiple flaws that I would have been not able to deal with as her boyfriend - a demanding workaholic who asks for all the advice she could possibly need but then does the exact opposite even when the opposite is completely moronic. I have seen her drop some decent guys - one in particular who she should have married - for absolute pieces of shit who treat her worse than the shit they are. Because of all that, she is now an overworked, single mother with almost no time to socialise with her friends and seems thoroughly miserable most of the time.
Having said that, I still count her as one of my closer friends (I don't have many friends by my definition of 'friend' mind you) and when we go out as part of a group, we still end up having as much fun as ever, such as at my friend's wedding a couple of months ago.
So perhaps in the end, I sacrificed attempting a potential relationship - some might say "dodged a bullet" - for a continued friendship and I say 'potential' I am pretty certain that she never saw me as boyfriend material.