S1.E1 ∙ Upper West SideFri, May 26, 2017In the pilot episode, Jack explores the Upper West Side's most memorable (to him at least) spots.Rate
S1.E2 ∙ Lower East SideFri, May 26, 2017Jack explores the Lower East Side with help from local guide (and Tinder date) Sheila Rathbone.Rate
S1.E3 ∙ BrooklynFri, May 26, 2017Jack visits Coney Island, Williamsburg, and more Brooklyn treasures as he distracts himself from one heartbreak with another heartbreak.Rate