We recently watched the highlights of Lynde's Hollywood Squares career:

1) Judging from the Q&As, how could anyone not have known at the time that he was gay?

2) It appears the Qs were tailor-made for Lynde, that he knew them in advance, and that he either a) thought of his own clever answer ahead of time or b) had the help of writers. I say this because he would've been TOO clever to be thinking of that stuff on the spot, time after time.

3) Yes, some of the stuff he said wouldn't have been PC (or allowed) today.