A decade and a half after their seminal indie film launched meteoric filmmaking careers, Splick and Jason find themselves staring at their own individual, pre-midlife crises. Having not spoken to one another since a late-nineties falling out, they're each grappling with the challenges of stalled careers and relationships, as the hands of time creep ominously past forty-o'clock. Splick's most recent TV show, centered around his character's perverse relationship with dessert foods, is unceremoniously cancelled by the network, forcing a return to his childhood bedroom at his mother's apartment in New York. Frustrated by a barrage of comments about the "good," "funny," movies he used to make with his old partner, Jason, Splick determines to seek him out and attempt a reunion.
Tired of the noise and madness of New York and the crushing conventions of late Eisenhower-era America, itinerant journalist Paul Kemp travels to the pristine island of Puerto Rico to write for a local San Juan newspaper run by the downtrodden editor Lotterman.
With his wife Elizabeth on life support after a boating accident, Hawaiian land baron, Matt King takes his daughters on a trip from Oahu to Kauai to confront the young real estate broker, who was having an affair with Elizabeth before her misfortune.