Barack Obama twice asked a previous girlfriend to marry him in the years before he met Michelle - and continued to see her after he met the future first lady - a new biography has claimed.
The former US president fell in love with Sheila Miyoshi Jaher at the start of his political career, she is quoted as saying in the book Rising Star: The Making of Barack Obama by David Garrow.
Now a professor at Oberlin College in Ohio, Ms Jager described in the book how her family had been against the proposed marriage because they were concerned about the young Mr Obama's "career prospects" and thought she was too young.
“In the winter of ‘86, when we visited my parents, he asked me to marry him,” she said, according to a review of the book by the Washington Post.
The couple stayed together but in the subsequent years, she said their relationship became subsumed by Mr Obama's political ambitions.
She said his questions about race were "directly linked to his decision to pursue a political career".
Mr Garrow quotes a friend of the coupe who recalls Mr Obama saying: "If I am going out with a white woman, I have no standing here".
Just days before departing for Harvard Law School Mr Obama again asked Ms Jager to marry him, but, she said, mostly out of "a sense of desperation" that their relationship was ending.
It was at Harvard that Mr Obama met Michelle Robinson, the woman who would become America's first lady.
But even in the nascent stages of this relationship he could not quite let Ms Jager go. The biography, which will be published on May 9, revealed that they kept meeting each other throughout the 1990-1991 academic year.
“I always felt bad about it,” Ms Jager told the author.
The book also reveals Mr Obama's first serious girlfriend was Genevieve Cook, a 25-year-old Australian primary school teacher, whom he fell for at a Christmas party in New York.
In the book Ms Cook describes how she slept with him on the night of their first date. She wrote in a journal she kept of their "passionate" love making, adding that it had all felt "very inevitable".
Ms Cook said that Mr Obama had taken cocaine in his early 20s with friends from Occidental College in Los Angeles. He has previously written about trying the drug when he was a teenager.
The biography also reveals that Mr Obama in his youth had been inspired by Donald Trump, the current president, with whom the former president has had an ongoing feud in recent years.
It published part of a book that Mr Obama wrote during his Harvard Law School days, but which was never published.
Mr Obama writes that Americans have a “continuing normative commitment to the ideals of individual freedom and mobility. The depth of this commitment may be summarily dismissed as the unfounded optimism of the average American — I may not be Donald Trump now, but just you wait; if I don’t make it, my children will.”