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Did Barack Obama Really Two-Time Michelle While They Were Dating? Here’s What New Biography Says

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Buried in Pulitzer Prize-winning historian David J. Garrow’s 1,400-page tome about former President Barack Obama’s rise to the White House is the headline-grabbing revelation that he had a serious relationship with – and proposed marriage (twice!) to – a woman other than wife Michelle.

Rising Star: The Making of Barack Obama also includes details that a young Obama may have continued to see his former flame, Sheila Miyoshi Jager, even after he met his future first lady. Some reports have breathlessly claimed that Obama cheated on Michelle.

“Barack and Sheila had continued to see each other irregularly throughout the 1990-1991 academic year, notwithstanding the deepening of Barack’s relationship with Michelle Robinson,” Garrow writes. “‘I always felt bad about it,’ Sheila confessed more than two decades later.”

Michelle Obama/Twitter
Getty; Library of Congress YouTube

But what’s the truth? Garrow spoke to Jager, now an Oberlin College professor, for the book. (She has declined to speak to PEOPLE.) Here’s what the author really says happened between Michelle, Barack and Jager – and the timeline of how it all went down.

RELATED VIDEO: Barack Obama Proposed to Another Woman Before Meeting Michelle, a New Biography Says

Rising Star: The Making of Barack Obama releases on May 9.

  • Obama and Jager dated for three years in the mid-1980s and even lived together in Chicago after being introduced by mutual friends.
  • Obama proposed to Jager twice; first in in 1986 when he was 25 and she was 23. She turned him down, saying “not yet” after her parents told her she was too young to get married.
  • Jager and Obama began to grow apart by 1987 as his political ambitions put a strain on their relationship. Jager moved to South Korea.
  • At the beginning of June 1989, Michelle Robinson, 25, was assigned by her top-flight Chicago law firm to mentor a Harvard University law student and summer associate named Barack Obama, age 27. Barack was impressed and immediately told another lawyer at the firm, “My mentor is really hot,” Garrow writes. Michelle was less amused and batted away Barack’s advances, telling him it would “look bad” if she dated him. Her friend at the time, Kelly Jo MacArthur, told Garrow that Michelle was known for her “conservative morals.”
  • On June 30, 1989, Michelle relented and agreed to go on one date with Barack. Her reluctant verdict: “I liked him a lot. He was cute, and he was funny, and he was charming,” she later recalled.
  • By mid-August, 1989, Michelle and Barack were seeing each other almost every day. She confessed to her brother Craig Robinson, “I really like this guy” and even asked her brother to meet up with Barack on the basketball court to size him up.
  • By December 1989, Barack and Michele’s six-month relationship was serious. He returned to Harvard to continue his legal studies, but she went to visit him just before exams. “After Michelle’s early December visit to Harvard, ‘it was clear that they were “a couple,”‘ her close friend … Kelly Jo MacArthur recalled,” Garrow writes. “‘The discussion turned fairly soon to whether they were going to get married or not.'”
  • In January 1990 Jager comes back into Barack’s life, Garrow writes. After Jager returned to the U.S., she took a teaching fellowship at Harvard. She admitted to Garrow that the fact that Barack was also in Cambridge may have unconsciously influenced her decision to look to the prestigious university. Barack told Jager in letters about Michelle, but also wrote about “his turmoil about our relationship.”
  • In early 1990, “we continued to see each other occasionally,” Jager told Garrow – “despite the deepening of Barack’s relationship with Michelle.”
  • Barack continued to carry on a long-distance relationship with Michelle as he made headlines across the country as the first black president of the Harvard Law Review in February 1990. He returned to Chicago during spring break in March to visit Michelle.
  • In June 1990, Obama went back to Chicago for summer break – this time to move in with Michelle and her family. They both worked at law firms and Barack spent his spare time doing community organizing.
  • Garrow does not elaborate on exactly how often Barack and Jager saw each other – or the extent of their intimacy – during this time, but by spring 1991, she met someone else and moved on. “As much as I loved him, I was relieved when our paths finally parted,” she told Garrow.
  • On July 31, 1991, Barack – having returned to Chicago – took Michelle to dinner at Gordon, a three-star restaurant. When she brought up marriage, by then a frequent topic, he demurred. When Michelle ordered the chocolate cake for dessert, she instead received a small box with a ring inside. Her response: “Yes, yes.”
  • On March 9, 1992, Barack wrote to Jager for the first time since they parted ways a year earlier. He informed her that he was engaged to Michelle.
  • On October 3, 1992, Barack Obama married Michelle Robinson at Trinity United Church of Christ in Chicago.
  • Obama continued to have limited contact with Jager through the years, including writing her a letter after the Sept. 11, 2001 terrorist attacks and calling her briefly in 2012 to ask whether she had been contacted by any biographers.