Everyone matures at various rates and comfort levels vary from person to person when interacting with the opposite sex, especially when there are these unique and somewhat foreign feelings that come about. I think that there is nothing wrong with women showing initiative, nothing whatsoever! We are not living in the sexist and oppressive society the world once embraced, girls / women are more than permitted to go for someone just as much as a man is entitled. I know I was quite shy at times--regarding the relationship with my 'lil redhead--but it has blossomed into a relationship more pleasureful and meaningful that one could have imagined because we have a natural ebb and flow. There are times she takes the reigns and I enjoy the ride wherein other moments I am quite the 'masculine' entity. Plus, some guys simply like a girl who is bold and speaks her mind outwardly without fear of judgement or impression; I find it to be quite attractive!!! (As long as it isn't to the degree of obnoxious dictator, of course.) Don't worry so much about him growing a pair and take a chance yourself, go out on a limb and see what happens... you could surprise yourself with the overwhelmingly delicious results! 

Besides, once the formalities of 'I like you' are over with you can help him find his balls ;)!

(... that last bit was to be humorous, btw!)

@)-----