David (Dudu) Gerstein was born in 1944 in Jerusalem to parents who immigrated from Poland. The family moved to Ramat Gan when he was four years old. Both he and his twin brother, Jonathan (Yoni) Gerstein, showed artistic talent from an early age. David's teacher, Batya Uziel, encouraged him to study painting. At the age of thirteen he was sent to a camp for the arts in Jerusalem, which he attended for several summers in a row. In high school, he took classes at the Beit Zvi Art Center in Ramat Gan with Rina Balktovsky Arnon. During his military service in the paratroopers he was stationed at Ein Gev for one year, where he painted a series of oils of fishing docks, boats and kibbutz landscape. While there, he met the artist Aharon Giladi, who encouraged him to pursue art. Upon completion of his military service, David applied to the Bezalel Academy of Arts and Design, Jerusalem, where he met Avraham Ofek, who had a marked influence on Gerstein's style.