I have severe aversion towards flirting...something in me utterly resists it?

well you should just try...force yourself the first time..even if its only a smile or something that will work...you should at least start somewhere, after the first try,keep trying...it gets easier and easier the more you practice...after you worked on your smiling then move on to more...eventually you will get that self esteem that you want, and it shouldn't take too long, also remember that guys are the ones who are supposed to ask girls out and make the bigger moves to soooooo, don't worry about asking him...also us guys are pretty much head over heels for girls so if you do try something once you get over your shyness then we'll be quite alright with it