When they were together for a long stretch, things did not work out well. But when they were apart, Jobs would pine for her. Finally, in the summer of 1989, he asked her to marry him. She couldn’t do it. It would drive her crazy, she told friends. She had grown up in a volatile household, and her relationship with Jobs bore too many similarities to that environment. They were opposites who attracted, she said, but the combination was too combustible. “I could not have been a good wife to ‘Steve Jobs,’ the icon,” she later explained. “I would have sucked at it on many levels. In our personal interactions, I couldn’t abide his unkindness. I didn’t want to hurt him, yet I didn’t want to stand by and watch him hurt other people either. It was painful and exhausting.”

After they broke up, Redse helped found OpenMind, a mental health resource network in California. She happened to read in a psychiatric manual about Narcissistic Personality Disorder and decided that Jobs perfectly met the criteria. “It fits so well and explained so much of what we had struggled with, that I realized expecting him to be nicer or less self-centered was like expecting a blind man to see,” she said. “It also explained some of the choices he’d made about his daughter Lisa at that time. I think the issue is empathy—the capacity for empathy is lacking.”

Redse later married, had two children, and then divorced. Every now and then Jobs would openly pine for her, even after he was happily married. And when he began his battle with cancer, she got in touch again to give support. She became very emotional whenever she recalled their relationship. “and made it impossible for us to have the relationship we once hoped for,” she told me, “the care and love I felt for him decades ago has continued.” Similarly, Jobs suddenly started to cry one afternoon as he sat in his living room reminiscing about her. “She was one of the purest people I’ve ever known,” he said, tears rolling down his cheeks. “There was something spiritual about her and spiritual about the connection we had.” He said he always regretted that they could not make it work, and he knew that she had such regrets as well. But it was not meant to be. On that they both agreed.

By this point, based on his dating history, a matchmaker could have put together a composite sketch of the woman who would be right for Jobs. Smart, yet unpretentious. Tough enough to stand up to him, yet Zen-like enough to rise above turmoil. Well-educated and independent, yet ready to make accommodations for him and a family. Down-to-earth, but with a touch of the ethereal. Savvy enough to know how to manage him, but secure enough to not always need to. And it wouldn’t hurt to be a beautiful, lanky blonde with an easygoing sense of humor who liked organic vegetarian food. In October 1989, after his split with Tina Redse, just such a woman walked into his life.