Starting Out in the Evening(2007)

Heather Wolfe, a 24-year-old graduate student, forces a meeting with broken-down Leonard Schiller, an out-of-print, sick old writer whose early works, written during the heyday of 1940s and 1950s New York intellectualism, forever changed Heather's life. Targeted as the subject of Heather's master's thesis, Schiller quickly falls under the seductive promise of her admiration, much to the distress of Ariel, his 39-year-old daughter, whose own struggles with failed romance and childlessness derail her energy. These mismatched souls gradually realize that their individual journeys, which they thought were drawing to a close, are in fact new beginnings.