There is no such thing as dumb questions in here.
Some people may give dumb answers though
Later in life?
I realised I needed glasses in my mid 30's.
I knew I needed them when stars were turning into blurry blobs, and street signs were getting impossible to read when driving.
As far as Astronomy, I don't wear glasses. The focuser focuses the image so I can see it.
That's what is good about focusers, you can take your glasses off if they annoy you when looking into EP's.