Ovinomancer
No flips for you!
Tge first is trivially true. It's a game played for entertainment, so yes, play should be entertaining to all.Certainly you should aim to entertain everyone at the table! And you seem to think that the purpose of social encounters is to 'win' them, which is not the case.
As far as "winning" social encounters, perhaps you just have meaningless social encounters where nothing is at stake, otherwise it would seem that the "win" condition is to get what you want or clise to it, no matter if you're using a formalized mechanic or if it's just acting well enough to convince Bob.