Six people in their early thirties come to terms with their own lives as they acknowledge the passing of a friend in this independent drama. Josh (Michael Knowles) was a successful and seemingly happy art dealer who one day jumped to his death from the window of his Manhattan high-rise apartment. A few days later, a handful of his friends arrive to help clear away his belongings and plan his funeral -- Sara (Susan Misner), his distraught former fiancée; Nick (Randall Batinkoff), a one-time professional athlete whose career is on the skids; Liz (Nicole Fonarow), an emotionally cool yuppie who arrives with her husband, Jim (Chris Henry Coffey); Dylan (Carl T. Evans), a misfit who still hasn't found his place in life; and Joann (Kristen Marie Holly), a socially and environmentally conscious type. No one seems to have any idea of what led Josh to take his own life. While clearing out the apartment, someone finds his journal, and temptation gets the better of them. As they begin to read it, they discover a side of their friend's life that they never knew before. Walking on the Sky was the first film for writer and director Carl T. Evans, who also appears as Dylan.