Diane Wilson Willoughby, 78, passed away peacefully on December 29, 2021 with her husband, daughter, and grandson holding her hands. Born in Norfolk, VA on December 23, 1943, Diane grew up in Norfolk, graduating from Gramby High School, and moved to Virginia Beach after marriage. She attended Frederic College from 1961-1964 and ultimately graduated from Old Dominion University with a Bachelor’s degree in Education.

Diane was predeceased in death by her mother, Matte Belle Wilson, father, Alvin Carlisle Wilson, and brothers, Alvin Carlisle Wilson, Jr. and Charles Frederick Wilson. She is survived by her husband William Robert “Bob” Willoughby, Jr, her daughter Kimberly Willoughby Harper (Eduardo Trinidad), her two grandsons, Logan, and Landon Harper, her three grandchildren, Rayna, Quinten, and Mykah Trinidad, and numerous members of her extended family and friends. Diane loved her two grandsons more than anything in this world. And she was loved by everyone that ever met her.

Diane began her teaching career with a long-term substitute teaching position at Shelton Park Elementary School. She then transferred to a full-time teaching position at Holland Elementary School. She quickly transferred to her beloved Thoroughgood Elementary School where she eventually retired from.

Diane loved laughing, going out to eat, shopping, and spending time at her beach house (especially with the Frederick ladies and the Neighbor ladies). She also loved fishing and visiting her grandson in Charlottesville. Diane loved life and made sure everyone around her was happy as well.

Memorial services will be determined later. A public notification will be made once the services have been scheduled.