F. Scott Fitzgerald's timeless tale of longing, loss, and the American Dream turns 100 this year, but its inspiration dates back to the author's own teenage heartbreak. The Great Gatsby's lavish parties and obsessive pursuit of love mirror Fitzgerald's real-life struggle with class, insecurity, and the painful gap between who he was and who he hoped to become.

A Love Story Born from Heartbreak

Fitzgerald's early life was spent on the outside of high society looking in. Born on September 24, 1896, in Saint Paul, Minnesota, his family lived on the city's prestigious Summit Avenue, but they lacked the wealth and social standing of their neighbors. This insecurity dogged him throughout his tenure at Princeton, where he desperately sought acceptance.

During his sophomore year at Princeton, 18-year-old Fitzgerald returned home to Saint Paul for Christmas break, where he attended a sledding party and met Ginevra King, a glamorous 16-year-old who embodied everything he longed for. King was born into the kind of wealth and status that fascinated him, and Fitzgerald was smitten.

A Courtship Marked by Heartbreak

Their romance blossomed, and they became passionate pen-pals. However, King continued to court the attention of other boys in her circle, admitting as much to Fitzgerald in a letter. Despite his repeated requests that she keep his letters to herself, King frequently reading them aloud to other gentlemen callers.

Fitzgerald's early letters to King were passionate and romantic, including a short love story he'd written entitled "The Perfect Hour", in which he imagined the two of them together at last. However, King's reply hinted at a darker reality, and their relationship ultimately ended in heartbreak.

Fitzgerald was devastated by the rejection and dropped out of Princeton, enlisting in the Army. His military career was marked by a sense of desperation, and he continued to write to King in a desperate bid to regain her affections. However, King's father arranged her marriage to William "Bill" Mitchell, an amateur polo player and son of a prominent Chicago bank head. Fitzgerald reportedly never stopped pining for King, and many scholars would characterize their romance as the most consequential relationship of his life.

A Legacy of Heartbreak

Fitzgerald would go on to marry Zelda Sayre, a sought-after Alabama socialite, but he reportedly never stopped pining for King. King is believed to be the inspiration for the character of Daisy Buchanan, one of the "careless" class of wealthy individuals who "smashed up things … then retreated back into their money," as The Great Gatsby reads.

Fitzgerald's meeting with King 20 years after their unhappy goodbye was marked by heartbreak and disappointment. King's tumultuous marriage to Mitchell had dissolved, and Fitzgerald was grieving his relationship with wife Zelda, whose debilitating mental health struggles necessitated full-time care at psychiatric hospitals.

Fitzgerald's final meeting with King was marked by a sense of regret and longing. He used this meeting as the basis for his short story, "Three Hours Between Planes," in which he detailed "a long and empty hour" between a pair of ex-intimates who "have nothing to say."

Fitzgerald's legacy of heartbreak continues to captivate readers to this day. As The Great Gatsby turns 100, it's clear that Fitzgerald's own experiences of love, loss, and longing continue to shape our understanding of the American Dream.

For more behind-the-scenes stories and little-known details about The Great Gatsby, check out the recent episode of the iHeartRadio podcast, Too Much Information, hosted by former PEOPLE editors Jordan Runtagh and Alex Heigl.

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