A problem with many women is excessive self-esteem, by which I mean an excessive impression of what they're worth. Twenty years ago, I knew a woman, a secretary at a small firm I worked for. She was 30 and gorgeous. She decided that she was going to marry a wealthy business owner, and would settle for nothing less. It didn't penetrate that her competition for the kind of guy she wanted was intense, with any number of gorgeous 25-year-old MBAs chasing the same guys. When I last saw her, she was 40, still unmarried, and delivering drinks in a bowling alley.
Guys have a big advantage over women in the dating game: we're the ones who are supposed to do the asking. Getting shot down multiple times results in a more realistic idea of who you stand any chance with. Lots of guys like to look at Victoria's Secret models -- few have any expectation of actually scoring a date with one. Too many women subscribe to the Cinderella/"Pretty Woman" fantasy: if they wait long enough, Prince Charming (or his modern equivalent as played by Richard Gere) will come along to take them away to his palace/mansion. They mostly wind up single, middle-aged, and bitter.