which conversation would be more difficult?

Among these pairs of contemporaries, which conversation is the least imaginable?

Casanova: 1725-1798
Kant: 1724-1804

or

Giordano Bruno: 1548-1600
Francisco Suárez: 1548-1617

Casanova/Kant may seem like the easy choice, but I’m not so sure: Casanova could probably have played the charming chameleon and come up with some topic that would interest Kant, if only to ingratiate himself for long enough to pull some sort of swindle. But it’s hard to imagine either Bruno or Suárez making enough of an adjustment to please the other.

And don’t forget– Casanova did meet Rousseau! Accompanied by some high society woman, Casanova let Rousseau do plenty of grim talking, but then he and the woman left and made fun of Rousseau’s social awkwardness for awhile. That’s probably what would happen with a Casanova/Kant meeting as well.