Vanessa Brassey has a very nice short essay at The Philosopher's Magazine, How Do Monet's Water Lilies Convey Regret?; it gets into deep issues without being in any way technical or difficult. I did want to comment on one point of it:
A first answer riffs off central cases. The picture looks regretful just as people do. But this doesn’t work for obvious reasons. When we see Jane as joyful, or Roger as regretful – we are connecting their look of joy or regret with a belief about them feeling joy or regret. But Water Lilies does not feel anything. We see the regret but we don’t believe the painting feels regretful.
This seems to confuse expressiveness with actual expression. We know that when we see Jane as joyful that this cannot be reduced to connecting her look of joy to a belief about her feeling joy because there is an entire profession, acting, that consists of people cultivating things like looks of joy that do not lead us necessarily to believe that they feel joy; and because there are fields of art, like cartooning, that depict things like looks of joy on characters that do not exist; and because there is a common act that we can discover, deception, in which people have things like looks of joy that we recognize don't go with feeling joy. Our navigation of these matters at the very least has an element of thinking of the actual through the lens of various possibilities, including at times counterfactuals or uncertain possibilities.
This perhaps ties to Brassey's larger point, though. Monet's lilies can convey regret because actual lilies under certain conditions can. We find landscapes as expressive as paintings of landscapes -- perhaps more expressive, at times. This would cause problems for Brassey's suggestion that "regret cannot manifest independently of a regretful somebody" but recognizing that we think the actual through counterfactuals and mere possibilities in landscapes means that we can recognize landscapes as also expressive in reference to 'somebody' (this landscape could be used to express regret, this landscape is as if a person is using it to express regret) without having to introduce a very complicated account of how this would work.
Other posts I've done that are relevant to this topic: Theories of Musical Expressiveness, Joyful Meadows and Sad Skies.
