They had no children together,[1] but they raised a daughter from her previous marriage to Toronto solicitor Harry Palmer, who died less than three years after the birth of the child.

[3] Olive first met her second husband John Diefenbaker in Saskatoon, Saskatchewan at a church where her father was working.

She attended McMaster University and the Ontario College of Education and in 1933 she started her career as a high school teacher.

[3] During her marriage to Harry, she stepped away from her profession but after his untimely death she started a new career as the director of child guidance for the Ontario Department of Education.

She would write her husband notes during his speeches with advice on how to appeal to the voters, for instance, during 1963 while John was delivering a speech in Cape Breton, Nova Scotia, Olive wrote him a note to mention the painting they had hung over their fireplace back at home which is a landscape of Cape Breton to help appeal to his audience.

An example is her white fitted floral hat bought by Mrs Bell Hall, an Ontario Councillor.