Obituary of Jenny O'Leary (DiPietro)
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 not just any ordinary person; she was a force of nature who blazed her own trail through life. She had an undeniable charm, and her beauty and intelligence shone through.
Born on August 21, 1978, Jenny was destined to be a star. She was an accomplished piano player and lovingly tended to her flock of cabbage patch dolls, her first babies. She knew from an early age that she wanted to be a mother, often telling people she wanted six children. She studied early childhood education to prepare for her envisioned life, not for a career.
In 2006 Jenny’s dream of motherhood came true and as she welcomed her first son Rocco, in 2008 her son Sabastian came along, and her daughters Rosalie and Adelaide were born in 2010 and 2012. She reveled in this life she had dreamed of. She delighted in making things magical despite being grossly outnumbered.
In between being an amazing mother and friend, she also mixed in various entrepreneurial adventures including Kiddie Swag, a Loot Bag company and Golden Heart Baby, a placenta encapsulation service as well as book clubs and kids playgroups.
Once all the kids were in school, she had to pivot – her dreams accomplished she started with a career. She began driving a school bus which allowed her to be home as much as possible while also filling her time. She was the world’s most enthusiastic bus driver – often stopping the bus to show her kids the snowy owls who lived in the marsh. Her expertise with children led Switzer Carty leaders to ask her to create a program for drivers to better understand and interact with kids with disabilities.
In 2017 she created and hosted a Rogers cable television show called Let’s Talk Mom. The show focused on helping women learn about the process of growing into motherhood and talking about the topics often left out of the conversation as women navigate this momentous time in their lives.
In 2018, Jenny and two friends co-founded an annual charity called the Great Canadian Gift Box which collects essentials for the underhoused people of Simcoe County in the wintertime.
In April 2023 she accepted a position at Benson Steel, and she took immense pride in learning and contributing to the team at Benson. She was a valued employee, and she fit in perfectly and helped keep everyone in check. Right Barb?
Following an initial battle with cancer in 2019, Jenny's spirit remained unbroken. She faced every challenge with a smile and a joke, reminding us all that laughter truly is the best medicine. Her resilience and grace were nothing short of inspirational. In October 2023 she learned that her cancer had returned and that she would need to embark on a challenging course of chemotherapy and immunotherapy. She went into remission in November 2024, but learned in March 2025 that again her cancer had returned.
Jenny’s family would like to extend their gratitude to Dr. Liauw and the amazing staff at the Margaret Bahen Hospice in Newmarket and to Sarah MacDougall, her ride or die.
To know Jenny was to know sunshine on your face. Her wit and joy for hosting were unmatched, as the hospice staff can attest to – we had to create a guest list to manage all Jenny’s visitors. She spent her last weeks in the company of her many friends and loving family.
Jenny's survivors include her four children, Rocco, Sabastian, Rosalie, and Adelaide, along with her dog, Stevie Nicks. She is survived by her mother, Marsha Pepin; her brothers, Shayne Boelk (Melanie) and Matthew O'Leary (Jessica); her husband, Paul; her sister-in-law, Dianna (Lenny); her brother-in-law, Bill (Diana); as well as aunts, uncles, nieces, nephews, and cousins. She will be remembered by her treasured friends Karen, Karen, Callie, Tammy, Cindy, Sonia, Anne, Natasha, Angela and Christa among many others. She is predeceased by her father, John O’Leary, and stepfather Ed Pepin as well as beloved dogs Bruno and Gus, Bianca and various other cats and too many fish to name. She also leaves behind a community that will miss her infectious energy and her ability to find something to be glad about.
A memorial gathering will be held on Wednesday, June 18, 2025 from 2-4 p.m. at Skwarchuk Funeral Home, 30 Simcoe Road in Bradford to celebrate Jenny's life and honor her memory. Instead of flowers, please consider making donations to your local Hospice in Jenny's name. And if you can, bring your best joke or funny memory – Jenny would have loved that.
Jenny's presence will be sorely missed, but her spirit will live on in the laughter and joy she brought to the people she loved. Rest in peace, Jenny – may your afterlife be filled with endless laughter, delicious chocolate, and the same reruns of all your favorite shows and movies. Thank you for being a friend ….