It changed over the years. It was always hard when the sexual/romantic context was apparent.
It was usually better with just friends, girls seemed to like me, I was kind of a "good guy".

Got easier with time. Was extremely difficult until I was about 20, 30 now and better.

It was usually them approaching me, and my current girlfriend actually helped me a lot with being at ease with women (meaning, herself). Though I still rarely feel the urge to approach them with sexual or romantic interest (even in the mind's eye).