Set over a series of late nights and early mornings in New York City, the film chronicles James (Shiloh Fernandez), a charismatic romantic who moves fluidly through the lives of numerous women. Across various encounters—ranging from passionate one-night stands and awkward casual dates to nostalgic reunions with ex-girlfriends—James seeks human connection while systematically sabotaging long-term vulnerability. As the dawn repeatedly breaks on his brief affairs, James is forced to confront his own shallow emotional patterns, fear of commitment, and growing internal loneliness.