Middle of the Night(1959)
Betty Preisser, an attractive 24 year old divorcee, works as a secretary in the hard-boiled atmosphere of Manhattan's garment district. Her workaholic boss Jerry (Frederick March) is feeling his own mortality. He's overworked and lonely. He's a 56 year old widower, but still enmeshed in his family obligations. His bossy older sister Evelyn has moved in with him and he has a married daughter Lillian and grandchild who live nearby.