Inside the Story of Barack Obama's College Love — the Woman He Proposed to Twice Before Michelle

Before Barack Obama became a global icon and US president, he shared a deep, formative relationship with a woman who didn't become his wife. A new biography uncovered the little-known story of the woman he asked to marry him, twice.

While many people view former US President Barack Obama and his wife Michelle Obama as the epitome of true love, love didn't initially go his way. Before Barack got down on one knee to ask Michelle to marry him, he was interested in another woman.

In David J. Garrow's biography, "Rising Star: The Making of Barack Obama," the author reportedly reveals that the former president was once in love with Sheila Miyoshi Jager. Their relationship occurred while Barack was living in Chicago during his early 20s.

Like the politician's mother, Jager, a woman of Dutch and Japanese descent, also studied anthropology. According to the book, the couple seemed like a natural fit, but the former anthropology student confessed to Garrow that their life together often felt isolating.

Jager described their relationship as "an island unto ourselves," adding that Barack would "compartmentalise his work and home life." At the time, Michelle's future husband worked as a community organiser and wrote fiction in his spare time.

Yet even then, he already believed he would one day become president of the US. Garrow noted that she quickly recognised "a deep-seated need to be loved and admired" in him.

Their relationship endured until marriage discussions began. Recalling how the proposal unfolded, Jager said, "In the winter of ‘86, when we visited my parents, he asked me to marry him."

Her parents initially disapproved of the marriage, expressing concerns over Barack's professional prospects and feeling their daughter was too young. So, Jager told him "not yet," although they continued dating.

A year after the proposal, Jager revealed that Barack's ambitions started to shift. She told Garrow, "I remember very clearly when this transformation happened, and I remember very specifically that by 1987, about a year into our relationship, he already had his sights on becoming president."

Jager was one of the few people he confided in about that ambition. But when it was time for him to leave Chicago to attend Harvard Law School, their relationship was already deteriorating. Despite that, Barack asked her to go with him and suggested they get married.

He made this second proposal even though he knew Jager was about to leave for a research trip to Seoul. She explained why she believed he proposed again. Jager believes it was driven mostly "out of a sense of desperation over our eventual parting and not in any real faith in our future." Ultimately, the couple parted ways.

Barack's former girlfriend earned her PhD in anthropology from the University of Chicago in 1994. She went on to become a professor of East Asian Studies at Oberlin College and has authored and edited four books on Korea and East Asia.

Jager now serves as Chair of East Asian Studies and Chair of Russian, East European, and Eurasian Studies. She later married historian Jiyul Kim. While she has an Instagram account that describes her as a mother, author, and anthropologist, it contains no posts.

Garrow's biography also explores other aspects of Barack's personal life. This includes the start of his relationship with Michelle during the 1990–1991 academic year. Despite dating Michelle, he continued to see Jager occasionally. Their contact eventually shifted to infrequent letters, especially as Barack's family life and political career began to take shape.

Though their paths eventually diverged, Jager played a significant role in shaping Barack Obama's early years. Her story offers a rare glimpse into the personal journey behind the public figure.