- His son is director Rodman Flender. Through Harold's daughter, Nicole Flender, Harold is the grandfather of actor Timothée Chalamet.
- He wrote for Sid Caesar in the 1950s, along with Woody Allen. When Allen later cast Harold's grandson Timothée Chalamet in his film A Rainy Day in New York (2019), he was initially unaware of the family relation.
- His parents, Sadie (Kasner) and Jacob Flender, were Austrian Jewish immigrants.
- Married to Enid S. (Rodman), who was born in New York, to Russian Jewish parents.
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