Cal Weaver appears to have it all: a successful career, a lovely home, wonderful kids, and a stunning wife, Emily. His idyllic existence takes a nosedive when he discovers Emily's infidelity and her desire for a divorce. Suddenly thrust into the dating scene at over 40, Cal feels lost and vulnerable. He meets Jacob Palmer, a charming womanizer who takes it upon himself to mentor Cal. With Jacob's guidance, Cal embarks on a journey of self-discovery, navigating the ups and downs of love and relationships in a modern world.