Young writer Ethan Less, while struggling to get over a broken heart, is suddenly faced with an empty bank account, a surprise visit from his estranged parents, and a realization of his addictive habits. Along with his group of friends, a true-to-life grouping of characters including Owen, who is convinced moving to Cleveland is his only chance of relief from his self prescribed insanity, Nicole, who, having reached her late thirties, is panicked she is unlovable, and the two very different long-time couples, Jones & Erika and Scott & Thomas, Ethan wanders New York City discussing life, debating change, and theorizing the acceptance of the good and bad life has to offer.