

Bobbie O’Leary passed on January 12, 2026, after a brief illness. Her funeral will be held 11 am, Saturday, January 31, at St. Mark’s Episcopal Church; family and friends are invited to a reception following the service. Bobbie will be laid to rest in Oaklawn Cemetery following the reception.
Born in Ocala, FL on December 6, 1920, to Thelma Stone and Robert Lee Van Osten, Bobbie spent her first 15 years in Ocala and moved to Jacksonville in 1935. She enrolled and graduated from Robert E Lee High School, class of ’37. After high school, she attended only one year of college at Tallahassee’s Florida State College for Women. With her father’s declining health, she had to leave college to return home supporting her mother and younger sister. Sadly, Bob Van Osten passed in 1939.
In 1941, Bobbie met the love of her life, Danny O’Leary. Their very first meeting was a lackluster, blind date which neither wanted to go on nor seemed to enjoy. Lucky, there was a 2nd date which led to love, which led to marriage, which led to 5 children, 8 grandchildren and 8 (and counting) great grandchildren.
Bobbie loved her family, friends, boxer dogs, sewing, smocking, knitting, needlepointing, cooking, reading, music of all genres, concerts, theater, scrabble, sudoku, bridge, crossword puzzles, driving long distances fast, dancing with dad, family camping trips, travel, clothes, shoes and Silver Oak. She enjoyed our Cummer Museum and Jacksonville Symphony, attended many Gator Bowls, Revelers and Seminole Club dances. If there was an opportunity to gather with friends, Bobbie was ready, just needed to know what she could bring.
In her spare time running the house and raising 5 children, Bobbie volunteered as Cub Scout, Boy Scout and Girl Scout leaders; she enjoyed time spent in the nursery at St Mary’s Church. She delivered Meals on Wheels. And with a deep love for literature, Bobbie helped brave adults enrolled in Learn to Read.
Bobbie was a member of the Garden Club, the 20-20 Book Club and the English Speaking Union. She was the official card carrier for her very precious and long-standing Friday bridge group. In Jacksonville, she enjoyed membership at the Seminole Club, Timuquana County Club, Florida Yacht Club, University Club and River Club. In Cashiers, NC, where Dan and Bobbie enjoyed their second home for many years, Bobbie held memberships at the Church of the Good Shepherd, Wade Hampton Country Club, Cedar Creek Racquet Club and High Hampton Colony Club.
Bobbie is pre-deceased by sons Danny (Mary Frances) and Michael (Becky), husband Danny, her sister Pepper and brother-in-law Ray. She is survived by sons Timothy and Patrick (Ruth), her daughter Robin; grandchildren Michael, Conor (Shannon), Chris (Nicole), Erin, Lauren (Ben), Devin (Meg), Brian (Jackie), Ryan; great grandchildren Aileen, Sean, Clara, Lillian, Eliza, Cullen, Nolan and Bobbie’s newest arrival, Patrick; many nephews, nieces and their children.
Bobbie expressed so much gratitude for her incredibly long, blessed and healthy life. Her innate kindness, intelligence and generosity touched more lives than she could comprehend. She sends her love to all.
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