Humans are constantly sensemaking, and the objects of that sensemaking include art and music. The first part of this talk will report on a study into how making sense of visual art can be influenced by music, and how music can enhance the appreciation of art. The study started from the hypothesis that art and music go best together when they convey similar emotions. In fact, the relationship between the two media is more complex; emotion has a role, but other factors are also important. The presence of a shared story or theme can also be a bond between the two media, whether the story or theme is explicit or created by the sensemaker. An impression of movement, or even lack of movement, is another potential bond. As a result of these insights, the study made some practical suggestions for using music to encourage the appreciation of art. People differ in their approach to, and capacity for, sensemaking, be it of art, music or in general. The second part of the talk will discuss current investigations into how we can use people’s reactions to art to understand both their emotional and cognitive responses. A variety of models have been proposed to measure aesthetic development, and sensemaking development generally. These frequently rely on expert assessment, but there is scope for automating this process, at least in part, including through the use of large language models.