This is one of those portraits very loosely based on life. I did the actual portrait from a live model, then, back at the studio, proceeded to go at it without photo resource, re-inventing him as I went along. It became a story for me..."what was he thinking about?.
I had been studying Sargent and thinking about the trip to Italy I didn't take this past spring.
I have always just loved JSS's rendition of the girls from Capri, so this was a chance to study those images again and play with replicating them, too. I did not like the negative space in my painting, so I painted a loose study, within my painting, of the head of the girl from Capri by Sargent. The story, then, became about this young man thinking about going to see the girls there or perhaps returning to see them..."should I go?" he says.
Hence the title.