For me, it would have to be with someone who has the same likes as I do.
I love Art.
So I would say The Art Gallery of N.S.W. in Sydney....we can have interaction looking at the Art...talking...people around, it all makes it go smoothly. No moments of ''what do I say''?
As long as he likes Art, it would be a wonderful place, and they have a great place to eat there too!