Ahead of the former president's 65th birthday, RadarOnline.com revisits his past love and loss with ex-girlfriend Sheila Jager. Years before Barack Obama met his wife, Michelle , he asked another woman to marry him – but she turned him down twice! 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. 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. In the late 1980s, just before leaving to attend Harvard Law School, Barack proposed again.