Calling It Quits(2009)

Sometimes your eyes don't see what your heart already knows.

Calling It Quits follows Dante Milestone, a burnt-out baby-boomer grappling with existential doubt and professional burnout. Disillusioned by work, his past, and questions about meaning itself, he abandons his career to search for happiness. What begins as a hopeful escape quickly unravels into a series of awkward, darkly comic missteps that leave him more lost than before. When Dante meets Cynthia, a mysterious spiritual guide, she helps him confront uncomfortable truths about himself. Through their unlikely connection, he discovers an answer that challenges everything he thought he wanted. Calling It Quits blends philosophical inquiry with wry humor, exploring whether happiness comes from external change or internal reckoning.