Jerusha Abbott spends her formative years as the oldest inmate of the John Grier Home, an austere orphanage where she bears the burden of strict institutional routines and endless chores. Her life changes abruptly when an anonymous trustee, amused by a satirical essay she wrote about the asylum, offers to finance her entire college education. The only condition is that she must write him a monthly letter detailing her academic progress and daily life, though he will never reply.
Transported from institutional monotony to a vibrant women's college, Jerusha discovers an entirely new world. She invents the affectionate nickname Daddy-Long-Legs for her guardian, based on his towering shadow, and fills her letters with exuberant accounts of her classes, dorm life, and evolving worldview. Despite initial struggles with a background that left her ignorant of basic cultural references, her quick wit and determination help her excel, particularly in English composition and literature.
As the years progress, Jerusha forms close bonds with roommates like Sallie McBride and Julia Pendleton, and spends her summers exploring the wider world, including a memorable stay at Lock Willow farm. She grows increasingly fiercely independent, striving to earn her own way through scholarships and writing prizes rather than relying entirely on charity. Along the way, she crosses paths with Julia’s charming uncle, Jervis Pendleton, whose unconventional warmth and shared intellectual curiosity gradually win her heart.
Complications arise when Jerusha’s deepening affection for Jervis leads her to reject a marriage proposal out of pride, fearing her unknown parentage and lack of social standing would burden his prominent family. Heartbroken and overwhelmed by misunderstandings, she retreats into her writing career, achieving early success with the publication of her stories.
The narrative reaches its emotional climax when Jerusha finally discovers the true identity of her mysterious benefactor. Visiting his New York residence, she learns that the enigmatic trustee who shaped her entire life and the man she loves are one and the same. The revelation dissolves the lingering barriers of her past, uniting her future with Jervis in a hard-won and deeply felt happiness.