Diane Montgomery moved from England to Canada as a small child when the family emigrated. After completing high school, she trained as a roof framer and carpenter, then worked in house construction and furniture building. As a mature student, she graduated from the Universities of Guelph (B.A. English and Drama) and Western Ontario (B.Ed.) before embarking on a teaching career. She then opened a business, with her husband, Robert, in quality control in the automotive parts manufacturing sector.

After several years, they changed their interests and built up a company to provide mobility equipment and supplies to the handicapped. "Girls' Night Out" was written as an assignment for a creative writing course taught by Judith Thompson and was the first student-written play ever produced in the University of Guelph 's George Luscombe Theatre.