i once wrote a long tirade about putting yourself in the woman's shoes and how is she going to interpret all the awkward posturing of a mysterious guy who's constantly going on dates with many girls and trying to smooch with them hours after meeting...
i didn't post it and i don't think i can articulate it well again.
but the big question I have is, you say from experience that it doesn't work out when you don't make any bold moves. So how many times have things worked out when you make these bold moves, i.e. developping into a relationship? or am i misinterpreting your motives and you are only after sex?