The meaning of this phrase depends pretty heavily on the meaning of confidence, and there are many. I had a woman coworker once tell me: the most attractive thing in a man is confidence and the least attractive thing is arrogance. Her differentiation of confidence versus arrogance helped clarify the former. I think what she said is probably true of all genders, not just women attracted to men, and probably extends beyond romantic relationships as well. I think it’d apply to teamwork in general. I get what you’re saying, but in my experience everyone has insecurities about somethings and confidence about others. The presence of insecurities doesn’t mean that one lacks confidence. Going a step further, the most insecure people generally do not acknowledge their insecurities. Gendered relationship scripts, like “a man must ask the woman out,” tend to take on less and less relevance the further removed I am from my high school years, but I do seek out progressive-minded people
