A Chicago neighborhood organizer in his early twenties, Barack Obama also dabbled in fiction writing in his leisure time. Sheila Miyoshi Jager, a beautiful Dutch-Japanese woman, struck up a friendship with him while he was living in the Netherlands. There was no doubt in my mind that they were meant to be together. Even though they were dating at the time that Obama was working as a community organizer, he confided in Jager about his ambitions to be president of the United States.
In the winter of 1986, Obama visited the parents of Jager's girlfriend, pleading for her hand in marriage. Ironically, Jager's parents were opposed to the union because they were worried about Obama's career prospects and thought their daughter was too young to marry. At the time, Obama was 25 and she was 23 years old. Obama was devastated by Jager's death, yet he did not break off their connection.
To complete his education, Obama enrolled in the Harvard Law School in 1988, and while there, he proposed to Jager a second time, to no avail. A "feeling of desperation about their approaching separation, rather than any true conviction in their future" fueled his proposition, she thought.
While attending Harvard, Barack Obama, then 28 years old, met Michelle Robinson, then 25 years old. Michelle had been given the responsibility of being Obama's mentor. With no hesitation whatsoever, Robinson decided to go on a date with the future President of the United States.
Previously, Michelle told the media that Harvard had paired her with Barack. It was his marriage to Michelle that sustained him as the world's most powerful man for so long after they fell in love. Suddenly, everything seemed to be falling into place.
Source: https://ynaija.com/meet-sheila-miyoshi-jager-the-woman-who-rejected-barack-obamas-marriage-proposal-twice/, https://www.independent.co.uk/life-style/before-michelle-barack-obama-sheila-miyoshi-jager-engagement-chicago-us-president-david-j-garrow-a7714771.html?amp
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