Gladys Marie Bollinger of Annapolis, MO passed away November 16, 2021 at the age of 92 years, 3 months and 10 days. She was born August 6, 1929 in Mound City, IL to the late Royal and Thelma Hale. In 1945, Gladys was united in marriage to Doyle Dover until his passing in 1989. Later in life Gladys was united in marriage to Paul Richard Bollinger who preceded her in rest on November 3, 2021. Gladys is survived by her little brother Lewis Hale and wife Joyce of Annapolis, MO, three nieces Shelley Hale and husband Rex Dunn of Annapolis, MO, Barbara Wren, Sandy Noel and husband Buddy, nephews Ronald Hale, Wayne Hale and wife Bobbie Kay, great-nieces Haley and Andrea, great-nephew Daniel, a sister-in-law Betty Hale, and many more loving family members and friends. Gladys is preceded in rest by her parents, her husbands Doyle and Richard, four brothers Leonard Hale, Roy Hale, Curtis Hale, Joseph Hale, three nephews Kevin Hale, Christopher Hale, Carl Hale, two nieces Janice and Lynn, two sisters-in-law Velva Hale, Mae Hale, and a nephew-in-law Roy Wren. Throughout her life Gladys worked several different jobs, one in which she served food to the elderly out of her local Community Center. She and her husband Richard were members of the First Baptist Church of Annapolis. A Celebration of Life will be held on Monday, November 22, 2021 beginning at 1:00 pm from the Cole Family Funeral Home. Visitation was held on Monday, November 22, 2021 from the Cole Family Funeral Home. Interment followed the services in the Bollinger Family Cemetery in Annapolis. Rev. Dan Pitchers will be officiating the services.