Records documenting the family life of Harvey J. Sims and his wife Florence Katherine Roos, who married October 29, 1902. Correspondence to Florence is sparse but includes three letters from her old friend Isabel Grace Christina "Bella" King, sister of William Lyon Mackenzie King. Florence had a literary bent and some of her writing is present in the collection, including her biography of Sheriff George Davidson.

A quantity of letters from Peter H. Sims to his son Harvey are present from 1888 (when Harvey was 17) to 1912. Peter gives opinions, advice, and instruction on every aspect of Harvey's life. He attempts to guide Harvey through the narrow path to success in the legal profession, counselling frugality, moral rectitude, and duty to family above all. He even gives Harvey step-by-step instructions on cleaning and painting his basement to make it healthy.

Correspondence from Harvey's mother Jemima is not as sympathetic. In 1898, on hearing a report that Harvey had been struck by a ball, she advises him strongly to give up football as "beneath the dignity of a practising barrister." Harvey never took this advice as he had a strong interest in many sports and made his mark in all of them: football, curling, and lawn bowling.
Also present in this series is correspondence from his sister Rella and her family, legal agreements, ephemera, football ephemera, lawn bowling scrapbook and trip ephemera.