Calling It Quits (2009)

Dante Milestone, a world-weary baby-boomer, is not happy. His struggles with everyday life, his past, even the question of 'the existence of a higher power', have led him to evaluate his own life. An assessment, that ultimately drives him to leave work and success behind, and set out on a quest in search of his happiness. But Dante soon learns that it's not that simple, for after a series of painfully humorous attempts fail to provide an answer, Dante sinks even deeper. It is not until he encounters Cynthia, a spiritual guide of sorts, that he uncovers the underlying truth and finally arrives at an answer that surprises even him.

Unfortunately the movie Calling It Quits is not yet available on HBO Max.