Set in modern day California, "Race You to the Bottom" follows Nathan (Williams), a travel journalist, as he is assigned to write about romantic hot-spots in the Napa Valley. He invites Maggie (Benson), the woman he has been seeing for months, to come along for a passionate weekend getaway. Trouble is, Maggie already has a boyfriend. And so does Nathan. What transpires is a seductive and heartbreaking journey through Napa’s wine country and into the complicated affair between these two dynamic young lovers.