In New York City, a twice-divorced, neurotic television writer finds himself in the throes of a complex romantic quagmire. As the writer grapples with his dissatisfaction with his work, he embarks on a love affair with his best friend's mistress. He's also constantly attempting to sort out his tangled relationships with the significant women in his life, including his teenage girlfriend who is half his age, and his ex-wife who is writing a tell-all book about their marriage.

The backdrop of Manhattan serves as both a playground and a reflective surface for the protagonist's inner turmoil. Amidst the iconic architecture and bustling streets, he juggles the challenges of his love life with episodes of existential contemplation and casual conversations with his intellectual circle. His journey is a rollercoaster of emotions and reflections on love, sex, friendship, and the very meaning of life in the modern world. As he navigates through the complexities of the human heart against this urban landscape, he comes face to face with the paradoxes of his own character.