I can't speak for other men but I've never led women on in that way, but mind you I've also never been a prolific dater. My first serious relationship and I put a ring on her finger.
I like that you opted for self reflection, but I don't think you should be too hard on yourself, the guys you have been seeing sound particularly douchey.
Try mixing up your social circle comfort zone a bit - I promise you that 90% of guys that confidently approach you will be dickheads. Most men are sitting at the back worrying that they will look like complete twats and usually miss the moment.