This is Lisa. You can see the first portrait I painted of her here.
This portrait took 3 sessions over a couple of weeks. The first session we talked for about an hour while listening to Joni Mitchell and drinking tea and came up with a brilliant idea of doing an oil portrait that we could both work on together. The idea was that I would begin the painting, then Lisa would work on it over the next week, then I would come back and work on it some more and it would go on like this until we had a portrait we both liked. Since I didn't bring any oils, we scavenged Lisa's studio for a canvas, paints, and brushes then set up an easel in her dining room since it had the best light. I got the painting to good place that afternoon though we both agreed she looked too stern in the painting. You can see that painting here.
The next week I arrived to find the painting exactly as I had left it! Instead, Lisa started a new painting - a self-portrait she had done from looking in the mirror. So I suggested I work on that painting instead of continuing on with the first one. I quickly discovered how difficult it is to work on a mirrored portrait. Everything is backward so you have to study the subject then flip the study in your mind and then try to paint. It's really hard to do so after a few minutes I gave up and returned to the original painting. I made some improvements and advanced the painting to the next level leaving the background mostly untouched.
The next time I returned Lisa had made further progress on her self-portrait. I continued working on my portrait and we talked about the background until I saw it in my mind as a golden light. I wrapped things up and brought it home and finished it. This is pretty much how I imagined it.