A lot of really great guys fall into the mind trap of "I'm a nice, easy going guy, so why are women not more receptive towards me?"
The reality is that you have to offer more than kindness and generosity, and sometimes even the world isn't enough if the chemistry isn't mutual. It does help to be attractive, but it also helps to have somebody that is fun to be around- somebody with hobbies and a life. It's hard to establish chemistry without having something to build it upon- the "you" that you know isn't what people are seeing. Think of it like you're trying to sell a house- it may be wonderful and cozy inside, but people are looking at the yard and the property first, right?
Gender stereotypes aside, most cultures have the mindset that the man makes the first move with no indecision: you ask the woman out (don't express romantic feelings, ask her out socially). When you jump the gun and dive straight into home plate with romantic feelings, she isn't going to be receptive, usually. When you ask her out, have an idea of what you want to do with her- absolutely no hint of "what do YOU want to do?". Have a plan and invite her to participate with you. If she flat out rejects you, don't dwell on it. There's a difference between playing hard to get and open rejection.
Rather than thinking of her as a potential romantic interest, think of her as a friend first- ask her out, build a connection. If there is chemistry between you two, she will be receptive to a second date. If she doesn't seem to be interested in spending time with you when you're offering it, don't cling on and act desperate: take the loss and move on, look for the next person you wouldn't mind trying to get to know... each failure, while morale crushing, will build your confidence in making the motions.
And try to make dating fun- it doesn't have to be this imposing monster. If you're not out having fun on an early date, you're wasting your time.