Hey, how about 2 cents from a woman?
Be yourself. Try not to dwell on it. That's woman's not worth it. You're going to meet a lot of "not worth it" women. Those are the women who like the losers.
There are women out there who want men like you. And yup - they meet a lot of jerks too. World is strange.
To use an M analogy, it's like M cars.
Unless maybe you're in some rich state or country, most of what exists out there are not M cars. You want a woman who deserves to be with you. You want a woman of calibre.
And guess what? Those types of women love being treated considerately like you treat them. And they'll treat you back the same or better.
Don't settle (or in this case waste your time thinking anymore) for/about a non-M woman.
Don't worry about what you did or didn't do. Sure, there are some things you learn by going through experiences and making mistakes. Only mistake I think you made is the $180 dinner. Not because it scares her or intimidates her or whatever. But because you wasted $180 on someone that didn't deserve it! But apart from those small things you learn along the way, there's nothing you need to change about yourself.
Being yourself and the gentleman you are is the most important thing.
The best thing you can do is exactly what someone mentioned earlier: Network.
But network not with the goal of finding someone. But to expand your experiences, learn something you've wanted to learn, etc. - network to maximize the enjoyment out of living and being who you are. Then you will naturally grow even more confident (regardless of how confident you are now or not).
And it's true that a high degree of *natural* confidence is particularly attractive.
Which does explain to a degree why some nice but not too bright girls (without much self-esteem) can fall for real losers who just have loads of confidence. Because they're too dumb to realize how much of a loser they really are...