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Meet The Woman Barack Obama May Have Proposed To Twice Before Michelle


(Photo by Scott Olson/Getty Images)

The woman who former President Barack Obama reportedly proposed to twice before he met Michelle had been identified as Sheila Miyoshi Jager. Details about their relationship were made public this week in a new presidential biography, Rising Star: The Making of Barack Obama written by Pulitzer prize-winning biographer David J. Garrow.

Jager, 53, is a professor at Oberlin college. She shared secrets of her relationship with Obama with Garrow; secrets that including their ongoing connection after he met the former First Lady.

“I always felt bad about it,” Jager told Garrow.

Jager received a Ph.D in anthropology from the University of Chicago, where she was studying in the mid-1980s when she met Obama, who was working as a community organizer.

The two dated for a few years before breaking up.

The book claims that Obama continued to see Jager one-and-off for at least a year after he had met Michelle. In the late 1980s, the couple lived together in Chicago and Jager described them as being “an island unto ourselves.”

The two even bought a cat together, which they named Max.

In the winter of 1986, Obama reportedly asked her to marry him while on a visit to her parents. Jager turned down the proposal as she was just 23 and he was 25.

They stayed together but she began to see that Obama had a “deep-seeded need to be loved and admired,” according to the book.

Jager told Garrow that Obama became “so very ambitious very suddenly.”

“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.”

However, Obama is said to have believed that he needed to “fully identify as African American to achieve his political goals – and believed that having a non-black spouse could damage his potential.

Jager is of Dutch and Japanese heritage.

Shortly before Obama left to attend Harvard Law School, he reportedly proposed to her again and again Jager turned him down.

She believed that his proposal was “out of a sense of desperation over our eventual parting and not in any real faith in our future.”



  • COED Writer
    A New York native & proud couch potato who loves all things pop culture. I can usually be found writing, making videos and ranking all the warriors in "Game of Thrones" based on their fighting prowess.