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HomeEntertainmentBarack Obama Proposed to Another Woman Before Michelle

Barack Obama Proposed to Another Woman Before Michelle

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Former president of the United States, Barack Obama, had an interesting love life long before Michelle Obama came into the picture.

Their love story kicked off in the mid-eighties and lasted long enough for the former couple to endure two proposals and an ill-fated reunion.

In the 2017 biography titled “Rising Star: The Making Of Barack Obama,” by David J. Garrow, the author gave the world a glimpse into former President Barack Obama’s life before Michelle Obama. Interestingly, that life included a romance with another woman, Sheila Miyoshi Jager.

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Sheila Jager | Image: YouTube/BookTv
Sheila Jager | Image: YouTube/BookTv

Jager began dating the former POTUS while in her early twenties. Barack, who was also in his twenties at the time, was two years older than her and had a different racial origin, which did not matter to the couple at first.

Sheila Jager, who resided in Chicago, was of Deutch and Japanese ancestry. Like the politician’s distant mother, the mystery ex has a degree in anthropology. She also passed through a teaching fellowship at Harvard, which facilitated her career path. 

Barack Obama’s former fiancé went on to become a professor at Oberlin College, Ohio.


Sheila Jager opened up about her awkward love story with Barack Obama, which began in Chicago, and ended for good following his marriage to Michelle.

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The two hooked up in the mid-eighties, while Barack was still living in Chicago and working as a community organizer. Both in their early twenties, they developed a connection neither could deny despite their differing races. 

As their love grew, Jager admitted that their life as a couple felt isolating because the former POTUS tended to “compartmentalize his work and home life.” As a result, they became an “island unto ourselves.”

Notwithstanding the strain in their relationship, the duo managed to make their romance work while it lasted.


Jager also went candid about her ex’s political dreams, which he began nurturing in his early twenties. Barack, who spent his free time writing fiction, nurtured an ambition to one day become the President of the United States. He confided in her, and she offered him her support, love, and admiration.

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Their relationship progressed at a fast pace, and the lovebirds began discussing marriage plans. During a visit to Jager’s parents in the winter of 1986, Barack Obama asked Sheila Jager to marry him. 

However, the anthropologist’s parents opposed the union because they felt their daughter was too young to settle down. Jager also revealed in the biography that Barack’s career prospects contributed to her parent’s disapproval.

Due to her parent’s stance, she responded to Barack’s proposal by saying, “not yet,” and he was willing to wait.


Their relationship hit a rough road in 1987 when Barack was 25. Jager explained how the politician suddenly became more ambitious. He believed having a non-African-American partner would hinder his political ambitions, and rightly so, considering they lived in Chicago.

The thoughts put pressure on their relationship, causing them to grow apart, with constant arguments about race and politics. Jager described that phase in Barack’s life as “feeling trapped between the woman he loved and the destiny he knew was his.”

He would go on to choose the latter. 


Barack decided to go to Harvard Law School to further his studies, but not before giving one last shot at their romance. Before leaving for Harvard, the icon asked Jager to go with him and become his wife.

Sheila Jager | Image: YouTube/Library of Congress
Sheila Jager | Image: YouTube/Library of Congress

Again, the Deutch-Japanese, who was then embarking on a research trip to Seoul, declined the offer. She explained in the new biography that this second proposal was more out of desperation over their parting than in “any real faith” in their future. Ultimately, her second refusal to become Barack Obama’s fiance led to their split.


A year after enrolling in Harvard Law School, Barack Obama met Michelle Robinson, who would go on to become his wife and mother of his kids. He met his future wife while serving as a summer associate at a law firm where she worked.  Before long, they became a couple.

Around that time, Jager came into the picture again after landing a teaching fellowship at Harvard. The 57-year-old admitted that meeting again rekindled their past romance. They continued seeing each other occasionally despite Barack’s serious relationship with Michelle.


Their affair, which Sheila Jager admittedly felt bad about, ended for good following Barack and Michelle’s marriage

Michelle went on to have the politician’s kids, and years later, served by his side as the first lady of the United States.

Barack Obama’s life today reflects perfection, with a wife that shares his ambition, two lovely daughters, and a reputation as one of the most influential men in the world.

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