Diana Gleason

Diana (Didi) Gleason had a wonderful life. She was a mother, wife, teacher, librarian, psychologist, and generous member of the South Shore community. A lifelong learner, she earned four master’s degrees that reflected her enduring curiosity and love of knowledge.

As an involved member of Linden Ponds Senior Living Community, Diana played bridge and bocce, took watercolor classes, and served on the landscape committee. She was an avid reader and belonged to four book groups. Diana loved playing board and card games and especially enjoyed winning. She continued to play golf even into her nineties. Diana started meditating 54 years ago and continued the practice daily. She traveled the world and had many adventures, making friends and cherished memories along the way.

Diana was greatly loved by her family and friends. She is survived by her children and their spouses: Chris Gleason and Lyn Enright, Heather and Patrick Sileo; her grandchildren and their spouses: Nick Gleason and Carolyn Simons, Josh Gleason and Pam Bertolini, Gretchen Sileo and Frank Abissi, Kora Sileo and Sean DeKay, and her great-grandchild: Cassiopeia Diana Gleason. She also had an extended family and many cherished friends. Diana always found the best in life and will be greatly missed.

A celebration of Diana's life will be held at Second Parish, 685 Main Street, Hingham, MA ,on Saturday, September 13, 2025, at 4 PM. In honor of her love of fashion and her favorite colors, we ask all attendees to please wear something green or blue to the service. In lieu of flowers, those who wish to remember Diana may donate to her favorite charities: Heifer International, the Audubon Society, Doctors Without Borders, or the World Wildlife Fund.