With regard to approaching people for potential dating, how much rejection do you take before you give up and stop trying?
For me, about 5 years worth after feeling I 'recovered' enough of my trashed self-esteem/worth/confidence after the soul-crushing wreck of my second relationship to try again and now I'm basically done. I don't approach women at all now in person or online (dating site) because I can't meet the criteria they want in a man for the most part. I also don't want to get married.
I usually don't approach or talk to any women at my work unless they talk to me first as there's too much risk of false SA/SH claims. This sort of also applies with any online interaction and general in-person experiences.
I know everyone is different with regard to this.