Jimmy is a semi-successful artist and playboy approaching middle age, when he decides it's time to step up and try love maybe before it's too late. He meets Rose, she's different in all the right ways. The head on her shoulders and her family values juxtaposed with Jimmy's childhood trauma and lack of family values makes for a potent match. But unexpectedly, with in the first year of the romance, she gets pregnant things get all too real, too quickly. The complexities of making a new relationship work, while raising a small child, ultimately tear them apart.

Donnie, Jimmy's closest friend, is going through a divorce that almost takes him down. After a long indecisive battle, he somehow makes it through, gets in shape, and with the help of modern technology makes a solid run at reliving his twenties. He pulls Jimmy along with him, forcing him into a date with a young, sharp and fierce gal named Binky, who basically ends up taking Jimmy to school. A night of sex, drugs, and a near-death experience lands Jimmy right back at square one, only now with a deep and painful longing for the family he started and subsequently walked away from.

This Isn't 40 explores the changing times for men and women, the effects of childhood cautionary tales, and the choices we make for the next generation.