In the early 1890s, ambitious yet impulsive Biff Grimes dreams of becoming a dentist while working as an apprentice in a blacksmith shop in New York City. His friend Hugo Barnstead, suave but unscrupulous, often leads him into trouble. Both fall for the same woman, the charismatic and enchanting Virginia Brush. Biff finds himself captivated by her charm while Hugo is determined to have Virginia for himself. At a Sunday picnic, Hugo orchestrates a double date without Biff's full knowledge, pairing Biff with Virginia’s practical yet thoughtful friend, Amy Lind. Biff reluctantly spends the day with Amy, but the two gradually develop an unexpected rapport. However, his heart is still with Virginia.

Biff's aspirations are further complicated by Hugo's manipulation and deceit. While attempting to woo Virginia, Hugo betrays Biff to serve his own ambitions. Caught up in Hugo's schemes, Biff faces setbacks that affect his work and relationships. As each character navigates their desires and morals, conflicts arise that test friendships and allegiances. When the situation reaches a boiling point, Biff is confronted with choices that will shape his future, personally and professionally. As he struggles with his feelings for both Amy and Virginia, Biff wrestles with the realization that life’s unexpected twists—and the true nature of those around him—might determine his happiness more than his own lofty dreams.