Barack Obama supposedly had another love he proposed to before he met Michelle. When he was a 25-year-old college grad living in Chicago, the future 44th president popped the question to Sheila Jager twice, according to a new book. The biography, Rising Star, says Jager lived with Obama in the Windy City in the 1980s. "In the winter of '86 when we visited my parents, he asked me to marry him," the book quotes Jager as saying. But her mom thought she was too young, so she declined.