After early education in country schools, Dear graduated from Louisiana State University and its Paul M. Hebert Law Center, both in Baton Rouge.

[1] On April 8, 1917, two days after the American entrance into World War I, Dear entered the United States Army officers' training camp at Fort Logan H. Roots in Arkansas, from which he received his commission as a second lieutenant of Field Artillery.

[1] In April 1921, Dear married the former Marion Suzanne Anderson (died 1969), a native of Chicago, Illinois, who later resided in Milwaukee, Wisconsin.

The couple had a daughter, Marion Dear Weber (1923–2009),[2] and a son, Cleveland "Cleve" Dear Jr. (1928–2015), a petroleum engineering graduate of both the Colorado School of Mines in Golden, Colorado, and LSU, who spent his later years with his wife and three children in Junction in Kimble County, Texas, where he died at the age of eighty-seven.

[1] In 1936, Dear ran to succeed Governor James A. Noe of Monroe, who had briefly served upon the death of Oscar K. Allen of Winnfield.