Where you go wrong is in taking the hesitant approach to asking a woman out – waiting for her to give you some unambiguous indication of interest (ideally, in large, red letters on a lighted billboard pulled by a pair of rented elephants).
That said, you shouldn’t be too hard on yourself. The psychological operating system now driving you (and all of us) evolved to solve ancestral mating and survival problems, and what was adaptive back then can be maladaptive today.
Take how we evolved to be deeply concerned about safeguarding our reputation. Reputation is essentially our social report card – others’ evaluation of the sort of person we are. It matters today, of course, but not in the life-or-death way it often did in an ancestral environment, where – per anthropologist Irven DeVore’s estimate – many people were with the same band of about 25 others for much of their life. Back then, if a guy got snubbed by a girl, it would be front-cave news; everybody would know and be laughing behind his back in short order.
Flash-forward to today. You’re in a bar. Some woman you hit on spurns you. Well, that blows – and more so if there are witnesses. But there are countless other bars – which means you can erase the embarrassing stain on your social rap sheet simply by trotting down the block to the next happy hour.
Ultimately, recognizing the mismatch between our evolved emotions and modern life helps you understand when the emotions driving you are counterproductively outdated – and basically stupid. In short, assuming that a woman you’re chatting up isn’t giving you a hate glare, ask her out. If she isn’t interested, she’ll let you know – either right then, with some brushoff like “Actually, I have a boyfriend …” or later, when you phone her and hear: “Home Depot, lumber department. How may I direct your call?”