The Woman Who Rejected Barack Obama’s Marriage Proposal TWICE Before Michelle

The Woman Who Rejected Barack Obama’s Marriage Proposal TWICE Before Michelle

By HuffPost on May 5, 2017
Barack Obama Mitchelle Obama
President Barack Obama and first lady Michelle Obama smile together as they wait to greet Italian Prime Minister Matteo Renzi and his wife Agnese Landini on the North Portico. | Getty

The couple that many Americans consider #relationshipgoals almost never was. According to a new biography of Barack Obama titled “Rising Star,” by Pulitzer Prize-winning biographer David J. Garrow, the 44th president of the United States asked another woman to marry him before Michelle — not once, but twice.

The book, which was reviewed by The Washington Post Tuesday, features details from an interview with Sheila Miyoshi Jager, an ex-girlfriend of Obama’s who is now a professor at Oberlin College.

Jager, who lived with Obama in Chicago while he was working as a community organizer in the 1980s, told Garrow that Obama proposed to her while they were visiting her parents in 1986. Jager turned him down because her mother felt she was too young for marriage. She was 23 at the time and Obama was 25.

Sheila Jagar, the woman that may have been Obama first lady
Sheila Jagar

The couple decided to remain together, and Jager told Garrow that shortly after Obama’s proposal, he began eyeing a run for mayor of Chicago, senate or even governor of Illinois, with his sights ultimately on the White House.

Garrow wrote that Obama believed he had a “calling,” and it was “coupled with a heightened awareness that to pursue it, he had to fully identify as African American,” the review quotes. Jager is of Dutch and Japanese descent and according to the book, this created a complication in their relationship.

Right before Obama left for Harvard Law School, he proposed to Jager a second time. She rejected his proposal because she was headed to Seoul for dissertation research.

Jager explained to Garrow that she thought Obama’s second proposal stemmed “mostly, I think, out of a sense of desperation over our eventual parting and not in any real faith in our future.”

A New York Times’ review of the book seemed to find Jager a dubious source, referring to her passages in Garrow’s book as “bitter musings.”

It’s also worth noting that Garrow interviewed Obama off-the-record for the book, and Obama read some of the manuscript. Garrow writes in the acknowledgments that the former president disagreed with “multiple characterizations and interpretations,” but that he’s thankful for Obama’s “appreciation of the scholarly seriousness with which I have pursued this project,” according to The Washington Post.

After his first year at Harvard, Obama met Michelle Robinson at a law firm where she worked and he was a summer associate.

“I remember being struck by how tall and beautiful she was,” Obama wrote of their meeting on

He asked Michelle out numerous times before she gave in.

“On our first date, I treated her to the finest ice cream Baskin-Robbins had to offer, our dinner table doubling as the curb,” Obama wrote. “I kissed her, and it tasted like chocolate.”

The couple dated for two years before Obama proposed.

“We were at a restaurant having dinner to celebrate the fact that he had finished the bar,” Michelle told ABC News in 2008. “And that was supposedly the reason. And then the waiter came over with the dessert and a tray. And there was the ring. And I was completely shocked.”

The couple wed in October of 1992, and the rest is history.

Read a full account on The Washington Post.


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