He was working as a sub-editor for the Enterprise newspaper in Charlottetown when he met Juliet Murray who was in her last year of high school at Queen's. They fell in love but the Murray family totally disagreed with this union because Starr was but a poor journalist with nothing but his pen and his ambition. Very harsh things were said to him that he felt he could never forget or forgive. The couple did marry without the Murrays' blessing and bought a small house in Charlottetown. Their daughter Emily was born the following year. Juliet Murray died four years later from sudden illness, and Starr was left alone to raise and provide for his child. They eventually moved to Maywood together into the "house in the hollow," and Starr taught his daughter at home. She soon manifested an interest in literature and Douglas Starr encouraged this, allowing her much space for creativity, but failing to provide adequate discipline. When Starr was diagnosed with tuberculosis, a rough local woman named Ellen Greene was hired to help around the house. Douglas Starr died shortly after Emily's eleventh birthday. The child was taken to New Moon Farm in Blair Water where she was raised by her mother's relatives.
Douglas Starr was portrayed by American actor Michael Moriarty on the Emily of New Moon television series. The series' character differs slightly from the book trilogy, as he is seen pulling his daughter from school and deciding to teach her himself because she was beaten by her teacher for standing up to him and defending a bullied Mi'kmaq boy.