June Bloom is a broke, cynical twenty-nine-year-old writers' assistant on the late-night comedy show, Stay Up with Hugo Best. Hugo Best is in his sixties, a beloved icon of TV and humor, and a notorious womanizer. After he unexpectedly retires and a party is held for his now unemployed staff, June ends up at a dive bar for an open-mic night and prepares for the sad return to the anonymous comedian lifestyle. What she's not prepared for is a run-in with Hugo at that dive bar. Nor for the invitation that swiftly follows: Hugo asks June to come to his mansion in Greenwich for the long Memorial Day weekend. "No funny business," he insists. June, in need of a job and money, confident she can handle herself, but secretly harboring the remains of a childhood crush on the charming older comedian and former role model, accepts. The exact terms of the visit are never spelled out, but June is realistic and clear-eyed enough to guess. Even so, as the weekend unfolds and the enigmatic Hugo gradually reveals himself, their dynamic proves to be much more complicated and less predictable than she expected.