Zachary "Zach" Hutton is a charming yet troubled writer who finds himself in a downward spiral due to his rampant womanizing and excessive drinking. Once a successful author, his creativity has been stifled by his self-destructive behavior. Zach's life begins to unravel even further after his long-suffering wife, Alex, finally has enough and leaves him. This separation pushes Zach into an identity crisis, where he realizes he has lost touch with what truly matters. His problem is compounded by frequent visits to a therapist, where he gives a convoluted recount of his hilarious but disastrous relationships. These sessions highlight his struggle to navigate the complexities of romance and self-worth while avoiding substance reliance.

As Zach attempts to piece his life back together, he is forced to confront the chaotic mess he has created. Surrounded by a colorful array of eccentric friends and lovers, Zach embarks on a series of misadventures—each more ludicrous than the last. He tries to reconnect with Alex and win her back, but his past indiscretions make this journey a turbulent one. Along this perilous path of reconciliation and self-discovery, Zach must come to terms with the fact that he can no longer rely on charm alone. With each mishap serving as both a comedic escapade and a poignant lesson, Zach is left to figure out if he can truly change and regain control over both his life and the relationships he holds dear.