Olivia Ruby Waugh

Her last smile

It is with love and gratitude that we share the peaceful passing of Mrs. Olivia ‘Olive’ Ruby Waugh, following a long struggle with congestive heart failure and progressive heart disease; at the Humber River Hospital in Toronto; on Thanksgiving Sunday, October 12, 2025; shortly after 10:00 a.m. in her 100th year.

Over the course of the last 3 weeks, his visits had become another part of their daily routine at the hospital. When her husband came into the room, he placed his hat and coat on the chair, and gently leaning over to kiss her forehead, she woke up when he said, ‘Good morning, sweetheart’; but raising her head just one last time… she could only smile in reply.

Olivia is survived by her faithful husband of over 50 years, Mr. James Gray ‘Jim’ Waugh, and her beloved nieces, nephews, family, and close friends.

Life and career

Born on Tuesday, November 3, 1925, Olivia built a distinguished career as a senior executive secretary at Moore Business Forms in Toronto, dedicating more than 40 years to the company. Her meteoric rise from a typist and stenographer into the executive boardroom earned her the office nickname ‘Mrs. Moore’. Colleagues and friends remember her profound mastery of French; her sharp mind, quick wit, and problem-solving skills; her attention to detail; and her often contrarian disposition, yet sublime sense of humour.

Meeting the man she called ‘Jim’

After the busy years, a quiet courtship and lasting love sprang from meeting the man who would become, at first, a friend from the church choir; soon after, her closest companion; and then, on one unforgettable day when she declared with a kiss, 'You have to meet my mother'—Jim became the love of her life.

In God's good time, after Olive and Jim met and started a new life together, they quietly married in the autumn of 1978.

Community and volunteer service

In retirement, Olivia volunteered with the West Park Healthcare Centre, a rehabilitation facility serving their continuing care patients in Weston. She also generously supported the fundraising committees, campaigns, and foundations at the former Humber Memorial Hospital and the new Humber River Hospital.

Family

It was only last year that the family gathered for what would become her last Thanksgiving reunion and dinner with most of her surviving family members and her husband, Mr. James Gray Waugh; nieces, Diane Hammond (Steve), Janice Knowles, Debbie Johnston (Dave), Margaret Sullivan, and Carole Duffy; and nephews, Bill Knowles and John Knowles (Suzanne).

Predeceased by her parents, Harry and Bertha Sullivan; her brother, Donald (Georgie); her sister, Dorothy Knowles; and her nephew, Robert Sullivan.

Interests and remembrance

Olivia was a voracious reader and music lover who enjoyed travelling and remained active through skating, cross-country skiing, golf, curling, tennis, and lawn bowling. She is remembered for her energy, warmth, and friendship, and for the happiness she found in serving her community.

Music and faith

Olivia found a deeper connection with her faith and found comfort in sacred music, singing with the Mount Dennis United Church Choir and travelling overseas to sing sacred choral music. Among her treasured memories were touring many European cathedrals, including Notre‑Dame Cathedral in Paris, and visiting the tomb of General Charles de Gaulle. She took delight in books and epic films such as Reds (1981) and Doctor Zhivago (1965); Broadway musicals, romantic comedies, and more recently, her favourite TV show — ‘The Big Bang Theory’.

Acknowledgements

The family would like to express our deepest gratitude to Olive’s devoted Personal Support Assistant, Michelle Arce, for her kind and attentive care over the past three years; to Dr. Jane Howell, her family doctor of more than 50 years; and to all the staff at the Mount Dennis Weston Health Centre ; and especially to the attending physicians at Humber River Hospital, Dr. Sagman, and all the nurses and staff in 13 West for their compassionate care during Olive's final weeks, ensuring Olive’s passage from this world was gentle, dignified, and peaceful..

Special thanks

In gratitude for a lifelong journey shared with so many dear souls, the family offers a heartfelt thank you to Olivia’s innumerable friends, neighbours, volunteers, and the members of the former Mount Dennis United Church and Graceview Presbyterian Church; West Park Rehabilitation Centre; the former Humber Memorial Hospital and the Humber River Hospital fundraising committees, campaigns, and foundations; and the Condominium Board at 240 Scarlett Road, for their love and support throughout her many years of faithful community service.

Olivia cherished the joy and the heartbreaking moments you shared, the countless memories, and the enduring close friendships she was so blessed to have over the many years she spent serving alongside all of you.

Service and memorial details

Olivia will be cremated at Sensible Choice Cremation and later interred at the Wideman Mennonite Church and Cemetery in Markham. A private Celebration of Life will be held for the family on Sunday, November 2, 2025.

Personal message from Jim

‘Olivia was my beloved wife, a woman of great courage who changed my life and became my closest and constant companion of more than 50 years and I will forever miss those sweet smiles every morning, the deep sighs, and her mischievous grins.’

Epilogue

For some, ‘True Love’ can be so much harder to lose — than it was to find.

Flowers and memorials

In lieu of flowers, please consider volunteering and supporting your local communities and charities.