Inside Barack Obama's Loves and Losses — Former Prez Was Turned Down by Another Woman Twice Years Before Marrying Michelle
Barack Obama dated Sheila Jager for several years before he met Michelle.
Aug. 3 2026, Published 4:05 p.m. ET
Years before Barack Obama met his wife, Michelle, he asked another woman to marry him – but she turned him down twice!
Ahead of the former president's 65th birthday, RadarOnline.com revisits his past love and loss with ex-girlfriend Sheila Jager.
Inside Barack Obama and Sheila Jager's Relationship
Sheila Jager is a historian and a professor at Oberlin College.
According to David Garrow's 2017 book, Rising Star: The Making of Barack Obama, the would-be POTUS popped the question in 1986 after several years of dating.
Jager was 23, and Obama was 25.
The now 62-year-old, who is a historian and college professor, said "not yet," because her parents believed she was too young to be married.
Still, the couple kept seeing each other for some time. In the late 1980s, just before leaving to attend Harvard Law School, Barack proposed again. However, Jager, suspected that it was more "out of a sense of desperation over our eventual parting and not in any real faith in our future," according to the book, and she turned him down for the second time.
Barack Obama and Sheila Jager split in the late 1980s.
On top of that, Jager also felt uncomfortable about his budding political career.
"He became. . . so very ambitious very suddenly," she shared with the author. "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."
Jager and Barack continued to occasionally spend time together after their breakup, even around the time that he began dating Michelle, something she said she "always felt bad about."
Barack and Michelle Obama met in the late 1980s.
But according to a source, Michelle initially wrestled with Barack's past romance.
"Friends claim Michelle can’t stand to even hear Sheila’s name. She wants her written out of the Obama story forever," a source once claimed in a resurfaced interview. "Barack has barely mentioned her – but that’s because he knows the trouble it would cause at home if he did!"
Barack and Michelle Obama's More Than 30-Year Marriage
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Michelle and Barack Obama got married in 1992.
Barack and Michelle met in 1989 when she was serving as his summer mentor at a Chicago law firm. Although she initially said no to a date due to concerns over being coworkers, she finally gave him a chance.
They tied the knot three years later and went on to welcome two daughters, Sasha and Malia, together.
Over their more than three decades of marriage, Barack and Michelle have weathered many ups and downs, including rampant rumors that they were on the brink of divorce. According to the mother-of-two, their secret to a happy relationship is being willing to seek guidance and put in the work
"I know too many young couples who struggle and think that somehow there's something wrong with them," Michelle told ABC News. "And I want them to know that Michelle and Barack Obama, who have a phenomenal marriage and who love each other, we work on our marriage. And we get help with our marriage when we need it."
