James's painting is a simplistic, child-like painting of a boat on water. The boat has a red body and white sails, and floats upon water that consists of dark blue triangles. In addition, there are clouds (two of which, curiously, are blue) and among them is a sun in the upper right-hand corner that largely resembles a spider. Throughout the image, there are pencil outlines of the objects that are painted. The painting largely lacks realism; obviously, art is not one of James's strengths.
The painting is introduced in "Put You First." Riley visits Kathy's house to asks for advice on what to get for James for their anniversary. Kathy informs Riley of James's love of art, and directs her towards the image hanging on her wall, claiming that James made it when he was sixteen.
Despite this being the first time the painting is introduced, it is not the first time that Kathy's house, and by default, the wall on which the photo hangs has been seen. It is possible that Kathy only recently hung the photo, therefore, or that it was added for the sake of the plot.