As long as you let your insecurities show you will create a barrier. Many people who come across as extremely confident are actually the ones with the lowest self-esteem and the most insecurities, but they just don't let it show. Some of the most successful and famous people have very low esteem but do their best to not let on to others in order to succeed.
And I don't like this idea of "approaching women", it sounds like something out of a wildlife documentary. Women aren't another species, they're just like you and me...except for a few obvious differences.
Opportunities always arise at the end of the day and one day POW! it will just happen. Jus' like that! Probably with a ladyfriend who you get the bus with thinking you were just good friends but she actually likes you and thats why you're friends in the first place and then you start to think that she's actually quite nice and then one day one when she's just about to get off at her stop she asks you out and you say yes but are still unsure whether its just because you are good friends but you hope its because she likes you but it can't be because "no-one would ever like me" and then you go on the date and then she has to spell it out to you that she really likes you which is very embarrassing for her and then you go all funny and tell her the same and then you both laugh and afterwards declare yourselves an item ending up living happily ever after together!
Or something like that anyway.