[VaedaStrike]

The relationship with a potential employer and a romantic interest have the same dynamics between creepy vs confident/hustling. We all have seen examples of both, but if any have tried to project confidence or to hustle to any significant and meaningful degree you run a non-trivial risk of appearing to cross lines / be creepy.

Often it isn’t one or the other. Steve Jobs was both a heartless ass at times while also being a brilliant hustler.

[EveYoung]

As most things in life, the perception of someone's actions are dictated by the outcome. If you succeed, your decisions might be considered bold and daring, but if you fail, they make you look arrogant or pretentious.