Shyness can also be a sign of low self esteem, if this is the case, just work on your confidence, observe people who are confident, their mannerisms, their body language, their attitude and practice in front of a mirror. I lack confidence a lot, and people always see me as a very confident and strong person! If you don't have it, fake it! Also don't be afraid of rejection, if a woman says no its either you re not her type which is quite normal, as everyone goes for a type of person or another, or maybe she's not up to it. Just think "its your loss, you don't know what you're missing". Keep having small talk with women, if the situation arises, on a bus stop, in an elevator, on the supermarket and if it gets weird or uncomfortable for you just remove yourself politely from the situation with a smile or pretend you re busy thinking of something else or doing something else, like checking your mobile for example. Hope it helps!