SIMPSON, Shirley Elaine Grubb, lovingly known as "Maw," peacefully passed away on September 26, 2023, at the age of 72 in Richmond, VA. She was born on October 6, 1950, in Richmond, to Doris Wilkins and Willie (WO) Grubb. Shirley was a cherished wife to the late Donald Simpson and a devoted mother to her late son, Michael Shawn Simpson. She was also preceded in death by her parents, her brothers, Michael, Buddy, Marvin and Steven and step grandson Jonah McKeever.

Left to cherish Shirley's memory are her daughter Amanda (Kevin), son Donnie (Brian), her stepchildren, Gerald and Sherri (Karen). Shirley's mischievous spirit lives on through her treasured grandchildren, Carter, Gabriel, and Dawson, as well as her step-grandchildren, Colleen and Shane. She also leaves behind her brother, Bill (Julie), sisters Teressa (Ricky), and Gail, sisters-in-law, Donna and Janet, and numerous uncles, an aunt, cousins, nieces, and nephews that she was so proud of. Joining in the journey of laughter and love is Shirley's significant other, Jerry O'Connell, whom she created countless memories with while always keeping him on his toes. We cannot forget the many Brazilian exchange students she hosted who called her mom.

She graduated from Meadowbrook High School but she was too cool for school. She was a pioneer for Work from Home as she found her true passion in running a legendary daycare for over 30 years; providing a warm and nurturing embrace, a safe haven to grow, and, of course, have a good ole time. Some to this day refer to her as their "second momma".

When Shirley wasn't busy keeping the neighborhood kids entertained, she would unleash her superpower as a shopping guru, decorating diva, and master of all things antique. She had an uncanny ability to find hidden treasures at yard sales or consignment shops, and would shop till she dropped. Let's not forget her melodic chops! Shirley loved listening to music, dancing, and singing karaoke.

A Celebration of Life for Shirley will take place on Sunday, October 1, 2023, 2 p.m., at the enchanting barn of Millstone Manor, located at 10600 Cosby Mill Rd, Quinton, VA, 23141. Get ready to don your brightest colors and sprinkle the event with laughter and joyful music as we honor Shirley's vibrant soul that loved everyone.

In lieu of flowers, please consider a donation in Shirley Simpson's memory to the Massey Cancer Center at VCU or Extended Stay at The Doorways at VCU.

To plant trees in memory, please visit the Sympathy Store.

Published by Richmond Times-Dispatch on Sep. 30, 2023.

Memories and Condolences
for Shirley Simpson

6 Entries

Diane Cooper Boone

October 1, 2023

Shirley and I were friends from the early age of 13. Experienced so many teen years together. Lost track after high school but each time I heard the name "Grubb" she was on my mind. We reunited a few years ago and picked up where we had left off. There plan to get together again but she became really sick. I will always remember her sweet smile, infection laugh and caring for other people. My prayers and thoughts are with the family today.

Larry Trammell

September 30, 2023

May your hearts soon be filled with wonderful memories of joyful times together as you celebrate a life well lived.

Sheri Galeano

September 30, 2023

I met this beautiful soul at Cracker Barrel while working in retail. We reveled in the fact we shared the same Birthday month and her name is same as my mom and she was a great friend. She loved big and she didn't judge. I will always remember the kindness she had towards every one and me. She was beyond special and she will definitely be missed.

Jewel Sharpe

September 30, 2023

I have known Shirley since 1984 when my husband and I bought a house on Swannanoa Trail, our realtor told me about this really wonderful sweet lady that babysat some of the neighborhood kids. My daughter Jennifer was almost two. Shirley had Little Donnie that was close in age. Jennifer and Donnie grew up together like brother and sister to this day. I am forever. Grateful for Shirley´s love, laughter. (lots of laughter.) her forever kindness that she gave to everyone that had the privilege of knowing Shirley. Both of my children, Jennifer and Louis calls mama Shirley their second mom. She truly treated all of her kids like they were her own. My heart and prayers goes out to her children, grandchildren and all of her family through these difficult times. We love you, mama Shirley, you will forever be missed. We will see you again on the other side. God will see us through these hard sad times.

Jewel Sharpe

Cody Baker

September 30, 2023

Shirley was an overall amazing person... I used to work with her at Cracker Barrel! She always was friendly and excited to see me when I came in as I was excited to see her too! She was a Retail Sales and also a Host. I was a Retail Sales, and when we worked together we worked together to accomplish a lot. But she truly is an overall amazing person, and our God has a beautiful soul and one day we will see her again. She always seemed happy when I seen her, and just being around her was such a breeze! Prayers go up for Shirley´s family!

Jamie collins

September 30, 2023

The first time I met Shirley was when she took over the big beautiful home at the other end of of the street. She gave me and our kids the grand tour as we always had the first horse; I believe his name was Fleetwood, meet us at the front fence whenever we walked by. Then when she joined cracker barrel as a hostess, we got to know one another and I was always happy to see her smiling face. Waiting on her when she got off or when she brought the family in to eat was a treat for me. She was always kind with nothing but happiness, joy and a serene personality. The last time I got to actually see and speak to her was right before we moved so hearing of her passing was definitely a shock. I had followed her updates and the last I knew she was getting better. She will definitely be missed. My family sends prayers and hugs to the family during this hard time.

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