Diana Vivian Dolan, legacy of love
Diana Vivian Dolan, lovingly known as DiDi to all who knew and cherished her, passed away peacefully Saturday, May 31, 2025, surrounded by her loving family after a brief hospitalization at ChristianaCare. She was 80 years young in spirit and heart.
Born in Washington, D.C., Sept. 21, 1944, to James and Grace McCully, Diana grew up with a love of family, food, and laughter that became the hallmark of her life. Her kitchen was always full of aromas, stories, and extra chairs for anyone who stopped by. She channeled her passion for food into a home catering business, and her warmth and wit lit up the bar she tended part-time at Ramshead Tavern in Annapolis, Md., where her brother Jimbo was the original owner.
Diana shared 44 years of marriage with her beloved husband, James “Jake” Dolan, before his passing in 2009. After retirement, they settled in Lewes, where DiDi truly came into her own—planting roots in the community as deeply as she planted herbs in her garden. She loved traveling, beach days, and hosting happy hours, where the drinks were cold and the stories even better. Beyond her love for entertaining, Diana was involved in several local civic associations and was a devoted supporter of Saint Jude Children’s Research Hospital.
She leaves behind a family full of laughter, strength, and love, her daughter, Jennifer Dolan; her son, Patrick Dolan; her devoted partner of 14 years, Fred Chidister; her brother, James “Jimbo” McCully and sister-in-law Vicky; her sister, Joyce McCully Ross and brother-in-law David; and her grandchildren, Elizabeth Dolan, Kevin Gonzalez, Delaney Gonzalez, Griffen Gonzalez and Madeline Gonzalez. Her spirit also lives on in the many nieces, nephews, cousins, and friends.
A celebration of DiDi’s life will be held on two occasions. The first gathering will be from 11 a.m. to 3 p.m., Thursday, June 12, at American Legion Post 17, 113 American Legion Road, Lewes, for her dear friends in the area. A second celebration will follow from 5 to 7:30 p.m., Thursday, June 19, 2025, at the Golf Club of South River, 3451 Solomons Island Road, Edgewater, Md., welcoming family and friends from Edgewater and beyond. All are invited to raise a glass, share heartfelt memories, and pay tribute to a woman whose warmth, humor, and love brightened the lives of so many.
In lieu of flowers, the family suggests contributions to Diana’s favorite charity, St. Jude’s Children’s Research Hospital, stjude.org/promotion/impact-giving-pm.html.
