Months later, “in the winter of ’86, when we visited my parents, he asked me to marry him,” Jager recalled.
Influenced by her parents—her mom liked Barack but thought her too young; her dad didn’t think the young man worthy—she said “‘not yet.'” They stayed together, though, for almost two more years.
In early 1987, Jager told Garrow, she witnessed her boyfriend becoming “someone quite extraordinary” after starting out, to her, “quite ordinary.” At the time, “he already had his sights on becoming president.” At the same time, Jager (who is half white, half Japanese) said, he became “brooding, quiet, distant—and it was only then, as I recall, that he began to talk about entering politics and race became a big issue between us.”
Still, Obama invited Jager to go with him to see his family in Hawaii that Christmas. By early 1988, however, Jager remembered realizing that she would never be able to marry Obama, that it wouldn’t be a fit for either of their aspirations. Barack went off to Harvard that fall—but Sheila had already moved out of their Chicago apartment, supposedly after taking a peek at the journal he kept under the bed.
They stayed in touch that first year, though.