I had very long hair cut 18 inches off at one time. I kept long hair for years because the guys liked it. But it was so boring to me, to easy to pull up in a ponytail. I fix it everyday now & I get compliments on mine everyday
But mine is not a bob which is boring too. Go try wigs on, even buy one wear it see what kind of feedback you get. I get a itch for long hair every now and then, so I have a few. I have never regreted it and don't know that I will ever grow it long again. A good stylist will be honest and tell you the best short cut that would fit your face. If you do cut it off donate it to locks of love, it will make a happy child or two.