After being dumped on her 30th birthday, Trish Santos works through her loneliness with help from her online art students, her two best friends, and a box of homemade self-help tapes given to her by the mysterious “mind painter” Doc Garcia.

Kenny is an ice cream vendor in Chicago with a crisp white uniform and an apathetic heart. When he encounters Lolita, a sharp-tongued but despondent insurance actuary, their heated conversation, natural spark and mutual hopelessness lead to an unusual proposal for a meet-cute: to travel to San Francisco, where they will jump off the Golden Gate Bridge together.

When St. Vincent sets out to make a documentary about her music, the goal is to both reveal and revel in the unadorned truth behind her on-stage persona. But when she hires a close friend to direct, notions of reality, identity, and authenticity grow increasingly distorted and bizarre.

Jack Jr, Miles Jr and the whole gang are back for one last wine-soaked journey prompted by the mysterious "Sommelier." Joined this time by Puck, a fan of The Napa Boys comics, the group will learn about love, loss, friendship and viticulture.