In 1916 she moved to New York to study photography, but she returned to Colorado Springs in 1918 after becoming seriously ill from influenza. Her mother hired a nurse, Elizabeth Warham Forster "Betsy", to care for her. Gilpin and Forster became friends and, later, companions. Gilpin frequently photographed Forster during the more than fifty years they were together, sometimes placing her in scenes with other people as though she were part of a tableau she happened to come upon. They remained together, with occasional separations necessitated by available jobs, until Forster's death in 1972. After Gilpin recovered she opened her own commercial photography studio in Colorado Springs. In 1924 the Pictorial Photographers of America awarded Gilpin her first New York show.