A writer from Los Angeles, who doesn't believe that relationships can last for him, struggles to mend his most recent failed relationship.

Buddy Gilbert (Gavin Bellour) is a struggling musician living in NYC. He spends his days touring the northeast with his pet turtle, playing community centers, dive bars and coffee shops because, he says, it beats a 9-to-5. One day, Buddy overhears his neighbor Susan (Elisabeth Moss) get in a particularly bad argument with her boyfriend and, although he barely knows her, he finds himself taking her out for some cheer-me-up ice cream.

Freewheeling distiller Terry wrangles his brother Tobin into one of his poorly planned schemes; a show focused on wine, whiskey and food. Tobin is frustrated when Terry shows up with a film crew comprised of eccentric personalities armed with dubious abilities. Meanwhile, Sly Fox, Tobin's biggest competitor for the coveted Golden World Wine Award is cleverly plotting to steal the prestigious award and break his multi year winning streak.