Rewind to the winter of ’86. We were visiting my folks when he popped the question, Sheila remembered. Her parents had their opinions, of course. Mom was fond of Barack but felt Sheila was too green for marriage. Dad, on the other hand, didn’t see Barack as son-in-law material. Sheila’s response? A gentle “not yet.” But they stuck it out, staying together for nearly two more years.
Fast forward to ’87. Sheila noticed a change in her boyfriend. He was morphing from “quite ordinary” to “someone quite extraordinary,” she told Garrow. And he had his eyes on the prize, aiming for the presidency. But there was a shift in his demeanor. He was becoming more introspective, more aloof. And that’s when politics and race started to dominate their conversations. Sheila, who’s half white and half Japanese, noticed these changes.
Despite the tension, Barack asked Sheila to spend Christmas with his family in Hawaii. But by the dawn of ’88, Sheila had a revelation. She knew she couldn’t marry him. Their dreams, their aspirations, they just didn’t align. Barack left for Harvard that fall, but Sheila had already packed up and moved out of their Chicago apartment. Rumor has it, she found his journal under the bed.
They kept in touch, though. At least for that first year.
