I’ve been thinking about this recently and it’s one of those innocent sayings that are quite insensitive. Growing up I heard this quite a lot, usually in response to being shy about asking someone out.
As an adult it’s hard to view this as an encouragement when the flip side is women dislike men with insecurities, women dislike men who feel vulnerable when putting themselves out there.
I don’t believe any of the connotations that I skewed from the phrase but it’s better to suggest “women love a man who are brave enough to fail” as encouragement rather, if you want a basic encouragement.
Just wanted to shar this somewhere appropriate
As a child it’s basically your parents supporting and believing in you (helps being good at something). As an adult it’s being really good at something and working on your childhood trauma of not supportive parents.
I don’t really get your point - since not being insecure just helps generally in life. And it’s always good to work on ones insecurities - be it just for oneselfs peace of mind.