I try to only if I know I'm going to get crap for it. I postponed telling my parents they were going to be grandparents up until last week. 😟My dad slapped me once for 'being stupid' and is still pretty angry, to the point he's offering me $3000 to get married right now.
But if it's something not as crazy but still touchy, depending on the person I'll mention it right away.