Arthur is a wealthy, whimsical playboy with no sense of responsibility and a penchant for living life on the edge. His carefree existence is enabled by the immense family fortune controlled by his stern mother, who tolerates his antics so long as they don't embarrass the family. However, her patience reaches its limit, and she gives Arthur an ultimatum: marry the cold, business-minded Susan or lose his inheritance. Susan is more interested in the union for its financial and societal convenience rather than any real affection for Arthur. Although he tries to comply, Arthur is repelled by the idea of marrying someone he doesn't love or even like, propelling him into a personal quandary.

Amid this dilemma, Arthur meets Naomi, a free-spirited writer living in New York. Drawn to her spontaneous and authentic nature, he begins to fall in love, realizing there's more to life than material wealth. As his feelings for Naomi grow, Arthur is forced to consider what truly makes him happy, questioning whether the security of his familial riches outweighs the freedom to chart his own course. Navigating between his mother's stringent expectations and his heart's true desires, he starts to contemplate the importance of self-discovery and genuine human connections. His loyal valet, Hobson, acts as his anchor, guiding him with wisdom and wit as he faces the most defining crossroads of his life.