After four years of chasing his stand-up comedy dream in Los Angeles, 34-year-old Scott Rollins (Ben Schwartz, Parks And Recreation) has crashed and burned. Left with little money and a fledging "career," Scott has no choice but to regroup, lick his wounds, and return to his parents' house in Long Island. While trying to figure out what to do next, he pines after his ex, Becky (Eloise Mumford), a successful photographer who has since married a former mutual friend. On a night out at a local bar, Scott strikes up an unlikely friendship with a very flawed, but very charming dermatologist, Marty (Billy Crystal, When Harry Met Sally...), who has a few regrets of his own. Marty and Scott help each other find the courage to face the failures in their lives and take stock in what their futures could bring.