It is not chutzpah. It sounds like that when people tell stories from own point of view they can frame as they wish. They sound cool when you listen to it as uninvolved poison. They are not cool at all when you are there in real life or in receiving end of it.
It is the fantasy vs reality difference. As much as you imagine yourself creative when doing these, other people see blinking red flags and boundary pusher that will cause trouble.
It is like those funny and cool characters on movies, that in reality you would cut out because they are assholes.
In pretty much every romantic comedy ever, there are probably "charming," "quirky," etc. behaviors that in the real world would be often/usually seen as creepy and stalkerish.
If the Op had a bit more credentials, and/or created something special, they might label it as "chutzpah" instead.
I recall a story (perhaps apocryphal) that involved Steve Jobs that was similar.