I always hated flirting. I stunk at it. Eventually, I found I was at my best when I accepted exactly who and what I was - for the better and for the worse.
Since then, I NEVER try to pretend to be the slightest bit better then I am. I would rather they were pleasantly surprised with me later on then moderately disappointed.
I am completely honest about myself and my thoughts and feelings. And I expect them to be relatively similar - or I will not retain a significant emotional interest in them.
They can ask me any question they like - and I will answer it honestly. Or I will tell her that I do not feel comfortable enough to tell her. But I try never to lie or exaggerate in the slightest. But if they ask a personal question; they better be prepared to answer one themselves - to the same extent of openness as I did. Otherwise, an emotional bonding between the two of us will be more difficult. And this is the same if I have just met her or have known her for 5 years, though I realize most people are uncomfortable doing it this way.
Basically, I treat her like an equal. A more feminine equal. And I try to never forget to treat her as I would wish to be treated.
It ain't rocket science. We are all in this thing called life together.
Don't try and use them. And don't be naive in case they are trying to use you because many WILL try and use you (both intentionally and unintentionally).
The bottom line is: everyone wants to be loved - even jerks (IMO).
I think you're on to something there. I was terrible at it too. When I was much younger I tried to always play it off and act cool, which in hindsight was just stupid. All I ever really had going for me (in terms of flirting) was a sense of humor.