Friends gather ‘round as we celebrate the extraordinary life of Jennifer Rebekkah Tammy O’Leary (DiPietro), the queen of Bond Head, who left us on May 17, 2025. Jenny was a force of nature — brilliant, beautiful, bold — who brought joy and light to all who knew her.
Born on August 21, 1978, Jenny’s passions and talents were evident from a young age — from accomplished piano playing to nurturing her beloved cabbage patch dolls. She always dreamed of motherhood, and fulfilled that dream with Rocco (2006), Sabastian (2008), Rosalie (2010), and Adelaide (2012).
Jenny was a natural entrepreneur, starting ventures like Kiddie Swag, Golden Heart Baby, and co-founding the Great Canadian Gift Box charity. She drove a school bus with enthusiasm, developed training programs for Switzer Carty drivers, and even created and hosted a Rogers TV show, Let’s Talk Mom.
In 2023, she joined Benson Steel, thriving as a valued team member. Jenny’s resilience in the face of cancer — diagnosed in 2019 and again in 2023 — was awe-inspiring. Through it all, she remained spirited, smiling, and full of humor.
Jenny is survived by her children, dog Stevie Nicks, mother Marsha Pepin, brothers Shayne Boelk (Melanie) and Matthew O’Leary (Jessica), husband Paul, and a wide circle of extended family and dear friends. She was predeceased by her father John O’Leary, stepfather Ed Pepin, and beloved pets.
A memorial gathering will be held on Wednesday, June 18, 2025, from 2–4 p.m. at Skwarchuk Funeral Home, 30 Simcoe Road, Bradford. Please bring a joke or funny memory in Jenny’s honor.
Donations in Jenny’s name may be made to your local hospice. Her warmth, wit, and unstoppable spirit will never be forgotten. Rest in peace, Jenny — may your afterlife be filled with chocolate, laughter, and endless reruns of your favorite shows.
Memories and notes of condolence may be shared at Skwarchuk Funeral Home.
