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
I’ve found that being confident about others ability to succeed or recover is very attractive to some people. “I think you can do this and if your can’t that will be ok and you will be ok and I will be here to help” is better than, “Of course I can do that.”