Robert Raymond Prettyman

It is with both sadness and celebration that we announce the passing of Robert Raymond Prettyman of Delmar, a beloved husband, father, grandfather, brother and friend, who left this world peacefully on Tuesday, July 1, 2025, surrounded by his loving family, at the age of 78. Robert was born on December 2, 1946, in Salisbury, Maryland, a son of the late Raymond and Mae (Hastings) Prettyman. He spent his life dedicated to family, hard work, and community.
A proud graduate of the Laurel High School Class of 1964, Robert answered the call of duty by serving in the U.S. Army, where he honorably protected our freedoms until his discharge in 1968. His unwavering work ethic shone brightly during his time at DuPont in Seaford, but his heart always longed for the open road. After retiring, he fulfilled his lifelong dream of being a truck driver. As the owner of Prettyman Trucking, Robert cherished over 25 years of hauling grain for Perdue, a job that brought him immense joy and satisfaction.
Robert's true passion, however, was his family. He shared laughter and love with his beloved wife of 55 years, Joyce, and treasured their adventures to Lancaster and Tennessee. The moments spent with his son, Daniel, and his granddaughter, Skylee, were the highlights of his life-she was truly the apple of his eye.
Robert is survived by his loving wife, Joyce Lynn (Simpler) Prettyman; his dedicated son, Daniel Prettyman; his cherished granddaughter, Skylee; his dear sisters, Clara Belle Littleton and Esther Hastings (Clarke); sisters-in-law, and Sue Headley (Joe) and Shirley Prettyman; and brother-in-law Wayne Simpler. He is also survived by many nieces and nephews.
In addition to his parents, he was preceded in death by brothers, Samuel "Sammy" Prettyman and Freddie Prettyman; a sister, Martha Ellen Prettyman; brothers-in-law, Richard Littleton and Joe Simpler; and sisters-in-law, Shirley Prettyman and Marlene Simpler.
A celebration of Robert's life will be held on Wednesday, July 9, 2025, at 2:00 p.m. at Short Funeral Home in Delmar, where a visitation will be held from 1:00 to 2:00.
Arrangements are in the care of Short Funeral Home in Delmar. Online condolences may be sent to the family by visiting www.shortfh.com.