Jessie Gleeson married Gerald Gleeson in 1852, settling in Bolingbroke, Nova Scotia. They raised four children: Jenny, two other daughters, and one son. Gerald frequently criticized Jessie and showed her little affection; their interactions consisted mainly of occasional marital duties, fostering her deep dissatisfaction and loneliness.

In June 1864, Bertha and Walter Shirley moved into the nearby Yellow House. Jessie initially made friendly visits to welcome them but soon stopped. When the school year commenced, she confided in Bertha that witnessing the loving intimacy between Bertha and Walter caused her pain, as it starkly contrasted with her own marriage. Despite this, Jessie expressed a strong desire for Bertha's friendship, suggesting they meet regularly during the day while their husbands worked.

Jessie was aware of Anne Shirley's infancy as a neighbor to Anne's biological parents in Bolingbroke. Her role in Anne's early life is contextual. Jessie was present during Anne's early childhood and knew the child survived. She cannot be the elderly woman Anne encounters in her birthplace during *Anne of the Island*, as that woman firmly believed the Shirley baby had died.