yep, i used to have same problem as you, but im getting better now. u said u has met hundreds of times with your friends i think that also mean u have met a load of girls in outside. but have you ever try to shows u are interesting in someone or do something that let her know u interesting in her? Confidence is a really important factor but over confidence is not too good, and again u should try to make the girl you interesting feels she is special than everyone else, sometimes you also need to be a little bit stand out n outgoing. maybe you can ask a girl to have a cup of tea with u rather than go out to have dinner with u, if u feel u want to spend somemore time with her, you can go shopping with her afterward then u can make a load of conversation while you shopping with her.
i hope this help u