Why are your hopes dashed?
.....and have often had difficulty understanding your type - the shyness, the reserve, the self control...
Is the person referred to in the blogs the same as the one under discussion or are there two or even 3 people referred to here?
If it is the same, your angst over her is just too intense and you must do yourself a favour and do something about it like ask her out now and worry about the consequences if (when) they arise.
If it is two or three people, time to take action: you seem to be on a self-destructive search for happiness where your chances are dashed by your own over-thinking before any progress is made at all. In this case, take action with the very next chick you meet and again, procrastinate the consequences. Don't worry today about what may never be tomorrow because guaranteed if you do, tomorrow you will be alone. again. carpe diem.