Crazy, Stupid, Love

A middle-aged husband and father whose wife asks for a divorce after an affair. He moves into his own apartment, frequents an upscale bar, and undergoes a flaunting, confidence-boosting phase. His journey swings from casual conquests to a deeper attempt to repair his marriage and redefine his priorities.

Cal's wife who initiates the divorce after discovering the affair. She seeks independence and redefines her life in the aftermath, while later contemplating reconciliation as Cal changes. Her choices drive the central conflict and emotional arcs of the story.

A young, charismatic man and seasoned seducer who mentors Cal in dating. He embodies confidence and charm, yet his relationship with Hannah reveals a different, more serious side of his life. His evolution parallels Cal's transformation.

Cal and Emily's teenage daughter who becomes romantically involved with Jacob. Her relationship adds tension to the blended family and highlights the complexities of love across generations.

The woman Cal seduces at the bar; a connection from his early rebound period. Her encounter with Cal becomes a catalyst for his later self-reflection and consequences within the story.

Cal and Emily's son who makes grand gestures to win the affection of Jessica. He navigates adolescence, school life, and the ripple effects of his parents' divorce on his own views of true love.

Bernie’s daughter and Robbie’s love interest. She becomes a focal point of teenage romance and the misunderstandings surrounding Cal's past relationships. Her actions drive key emotional moments in the narrative.

Cal's best friend whose own relationship dynamics shift as his wife sides with Emily. Bernie provides comic and heartfelt support while navigating friendship, loyalty, and family changes.

Emily's affair partner who represents the catalyst for the divorce. He reappears at moments of tension, underscoring the consequences of infidelity and later competing for emotional space in Emily's life.