Barack Obama proposed to a serious girlfriend before he met Michelle, a new biography of the former president reveals.

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“Rising Star: The Making of Barack Obama” by David J. Garrow was reviewed by The Washington Post on Wednesday, and the write-up includes the juicy story of Obama’s old girlfriend, Sheila Miyoshi Jager.

According to Jager, Obama proposed to her in the winter of 1986. However, her parents protested, since she was in her early 20s and two years younger than Obama.

The couple kept dating, but his political ambitions got in the way of their relationship.

“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,” Jaeger told the biographer.

Race was another major issue for the two, as Jager was of Dutch and Japanese heritage and Obama was increasingly embracing his black identity as an aspiring Chicago politician. Notably, Obama started going by Barack after being called Barry for most of his life.

A mutual friend of the couple told Garrow he remembered Obama saying, “The lines are very clearly drawn…If I am going out with a white woman, I have no standing here.”

Obama asked Jager to marry him one more time, right before he went off to Harvard Law School, but the relationship was coming to an end.

He went on to meet future first lady Michelle Obama at a Chicago law firm where he was a summer associate after his first year at Harvard.

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Read the whole story in The Washington Post’s review of Garrow’s book “Rising Star: The Making of Barack Obama” here.

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