As the daughter of a prominent McGill medical professor, Gwendolen Marjorie Howard was acquainted with several of her father's former students and their families. One such family was that of the Montreal anatomist, surgeon, and McGill medical instructor, Dr. Francis John Shepherd. Having been a student under Dr Howard along with William Osler, Dr Shepherd and his family remained in contact with the Howard children after the death of their parents.

Born in Como, Quebec, Dr. Shepherd graduated in medicine from McGill University in 1873. After further studies in Britain and Europe, he returned to McGill in 1875 as Demonstrator in Anatomy. In 1879, he joined the staff of the Montreal General Hospital. Dr. Shepherd also served as Professor of Dermatology from 1908 to 1913, and as Dean of the Faculty of Medicine from 1908 to 1914, retiring as Emeritus Dean and Professor in 1919.

Like Miss Howard's friends the Cloustons, the Shepherds spent a considerable amount of time west of the city near the Lake of Two Mountains (Lac des Deux-Montagnes). While the Clouston's country estate was located on the Island of Montreal in Senneville, the Shepherd's country home was in Como, across the lake, at the mouth of the Ottawa River. Many of the photographs of Dr Shepherd, his two daughters, Mary Cecilia (1881-1971) and Dorothy (b. 1886), and their older brother Ernest (1879-1918) were taken either at the family's Como home, across the river at Oka, or boating near the junction of the Ottawa and Saint Lawrence Rivers.

Closest in age to Gwendolen Marjorie Howard, Mary Cecilia Shepherd (often referred to as "Cecil") married the Montreal architect Percy Erskine Nobbs in 1909. It was Nobbs who was called upon to design McGill's Osler Library of the History of Medicine in memory of his father-in-law's former colleague and friend.

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