Mona Simpson and her fiancé, Richard Appel, 1991

Joan Baez

In 1982, when he was still working on the Macintosh, Jobs met the famed folksinger Joan Baez through her sister Mimi Fari?a, who headed a charity that was trying to get donations of computers for prisons. A few weeks later he and Baez had lunch in Cupertino. “I wasn’t expecting a lot, but she was really smart and funny,” he recalled. At the time, he was nearing the end of his relationship with Barbara Jasinski. They had vacationed in Hawaii, shared a house in the Santa Cruz mountains, and even gone to one of Baez’s concerts together. As his relationship with Jasinski flamed out, Jobs began getting more serious with Baez. He was twenty-seven and Baez was forty-one, but for a few years they had a romance. “It turned into a serious relationship between two accidental friends who became lovers,” Jobs recalled in a somewhat wistful tone.

Elizabeth Holmes, Jobs’s friend from Reed College, believed that one of the reasons he went out with Baez—other than the fact that she was beautiful and funny and talented—was that she had once been the lover of Bob Dylan. “Steve loved that connection to Dylan,” she later said. Baez and Dylan had been lovers in the early 1960s, and they toured as friends after that, including with the Rolling Thunder Revue in 1975. (Jobs had the bootlegs of those concerts.)

When she met Jobs, Baez had a fourteen-year-old son, Gabriel, from her marriage to the antiwar activist David Harris. At lunch she told Jobs she was trying to teach Gabe how to type. “You mean on a typewriter?” Jobs asked. When she said yes, he replied, “But a typewriter is antiquated.”

“If a typewriter is antiquated, what does that make me?” she asked. There was an awkward pause. As Baez later told me, “As soon as I said it, I realized the answer was so obvious. The question just hung in the air. I was just horrified.”

Much to the astonishment of the Macintosh team, Jobs burst into the office one day with Baez and showed her the prototype of the Macintosh. They were dumbfounded that he would reveal the computer to an outsider, given his obsession with secrecy, but they were even more blown away to be in the presence of Joan Baez. He gave Gabe an Apple II, and he later gave Baez a Macintosh. On visits Jobs would show off the features he liked. “He was sweet and patient, but he was so advanced in his knowledge that he had trouble teaching me,” she recalled.

He was a sudden multimillionaire; she was a world-famous celebrity, but sweetly down-to-earth and not all that wealthy. She didn’t know what to make of him then, and still found him puzzling when she talked about him almost thirty years later. At one dinner early in their relationship, Jobs started talking about Ralph Lauren and his Polo Shop, which she admitted she had never visited. “There’s a beautiful red dress there that would be perfect for you,” he said, and then drove her to the store in the Stanford Mall. Baez recalled, “I said to myself, far out, terrific, I’m with one of the world’s richest men and he wants me to have this beautiful dress.” When they got to the store, Jobs bought a handful of shirts for himself and showed her the red dress. “You ought to buy it,” he said. She was a little surprised, and told him she couldn’t really afford it. He said nothing, and they left. “Wouldn’t you think if someone had talked like that the whole evening, that they were going to get it for you?” she asked me, seeming genuinely puzzled about the incident. “The mystery of the red dress is in your hands. I felt a bit strange about it.” He would give her computers, but not a dress, and when he brought her flowers he made sure to say they were left over from an event in the office. “He was both romantic and afraid to be romantic,” she said.

When he was working on the NeXT computer, he went to Baez’s house in Woodside to show her how well it could produce music. “He had it play a Brahms quartet, and he told me eventually computers would sound better than humans playing it, even get the innuendo and the cadences better,” Baez recalled. She was revolted by the idea. “He was working himself up into a fervor of delight while I was shrinking into a rage and thinking, How could you defile music like that?”

Jobs would confide in Debi Coleman and Joanna Hoffman about his relationship with Baez and worry about whether he could marry someone who had a teenage son and was probably past the point of wanting to have more children. “At times he would belittle her as being an ‘issues’ singer and not a true ‘political’ singer like Dylan,” said Hoffman. “She was a strong woman, and he wanted to show he was in control. Plus, he always said he wanted to have a family, and with her he knew that he wouldn’t.”

And so, after about three years, they ended their romance and drifted into becoming just friends. “I thought I was in love with her, but I really just liked her a lot,” he later said. “We weren’t destined to be together. I wanted kids, and she didn’t want any more.” In her 1989 memoir, Baez wrote about her breakup with her husband and why she never remarried: “I belonged alone, which is how I have been since then, with occasional interruptions that are mostly picnics.” She did add a nice acknowledgment at the end of the book to “Steve Jobs for forcing me to use a word processor by putting one in my kitchen.”

Finding Joanne and Mona

When Jobs was thirty-one, a year after his ouster from Apple, his mother Clara, who was a smoker, was stricken with lung cancer. He spent time by her deathbed, talking to her in ways he had rarely done in the past and asking some questions he had refrained from raising before. “When you and Dad got married, were you a virgin?” he asked. It was hard for her to talk, but she forced a smile. That’s when she told him that she had been married before, to a man who never made it back from the war. She also filled in some of the details of how she and Paul Jobs had come to adopt him.

Soon after that, Jobs succeeded in tracking down the woman who had put him up for adoption. His quiet quest to find her had begun in the early 1980s, when he hired a detective who had failed to come up with anything. Then Jobs noticed the name of a San Francisco doctor on his birth certificate. “He was in the phone book, so I gave him a call,” Jobs recalled. The doctor was no help. He claimed that his records had been destroyed in a fire. That was not true. In fact, right after Jobs called, the doctor wrote a letter, sealed it in an envelope, and wrote on it, “To be delivered to Steve Jobs on my death.” When he died a short time later, his widow sent the letter to Jobs. In it, the doctor explained that his mother had been an unmarried graduate student from Wisconsin named Joanne Schieble.

It took another few weeks and the work of another detective to track her down. After giving him up, Joanne had married his biological father, Abdulfattah “John” Jandali, and they had another child, Mona. Jandali abandoned them five years later, and Joanne married a colorful ice-skating instructor, George Simpson. That marriage didn’t last long either, and in 1970 she began a meandering journey that took her and Mona (both of them now using the last name Simpson) to Los Angeles.

Jobs had been reluctant to let Paul and Clara, whom he considered his real parents, know about his search for his birth mother. With a sensitivity that was unusual for him, and which showed the deep affection he felt for his parents, he worried that they might be offended. So he never contacted Joanne Simpson until after Clara Jobs died in early 1986. “I never wanted them to feel like I didn’t consider them my parents, because they were totally my parents,” he recalled. “I loved them so much that I never wanted them to know of my search, and I even had reporters keep it quiet when any of them found out.” When Clara died, he decided to tell Paul Jobs, who was perfectly comfortable and said he didn’t mind at all if Steve made contact with his biological mother.

So one day Jobs called Joanne Simpson, said who he was, and arranged to come down to Los Angeles to meet her. He later claimed it was mainly out of curiosity. “I believe in environment more than heredity in determining your traits, but still you have to wonder a little about your biological roots,” he said. He also wanted to reassure Joanne that what she had done was all right. “I wanted to meet my biological mother mostly to see if she was okay and to thank her, because I’m glad I didn’t end up as an abortion. She was twenty-three and she went through a lot to have me.”

Joanne was overcome with emotion when Jobs arrived at her Los Angeles house. She knew he was famous and rich, but she wasn’t exactly sure why. She immediately began to pour out her emotions. She had been pressured to sign the papers putting him up for adoption, she said, and did so only when told that he was happy in the house of his new parents. She had always missed him and suffered about what she had done. She apologized over and over, even as Jobs kept reassuring her that he understood, and that things had turned out just fine.

Once she calmed down, she told Jobs that he had a full sister, Mona Simpson, who was then an aspiring novelist in Manhattan. She had never told Mona that she had a brother, and that day she broke the news, or at least part of it, by telephone. “You have a brother, and he’s wonderful, and he’s famous, and I’m going to bring him to New York so you can meet him,” she said. Mona was in the throes of finishing a novel about her mother and their peregrination from Wisconsin to Los Angeles, Anywhere but Here. Those who’ve read it will not be surprised that Joanne was somewhat quirky in the way she imparted to Mona the news about her brother. She refused to say who he was—only that he had been poor, had gotten rich, was good-looking and famous, had long dark hair, and lived in California. Mona then worked at the Paris Review, George Plimpton’s literary journal housed on the ground floor of his townhouse near Manhattan’s East River. She and her coworkers began a guessing game on who her brother might be. John Travolta? That was one of the favorite guesses. Other actors were also hot prospects. At one point someone did toss out a guess that “maybe it’s one of those guys who started Apple computer,” but no one could recall their names.

The meeting occurred in the lobby of the St. Regis Hotel. “He was totally straightforward and lovely, just a normal and sweet guy,” Mona recalled. They all sat and talked for a few minutes, then he took his sister for a long walk, just the two of them. Jobs was thrilled to find that he had a sibling who was so similar to him. They were both intense in their artistry, observant of their surroundings, and sensitive yet strong-willed. When they went to dinner together, they noticed the same architectural details and talked about them excitedly afterward. “My sister’s a writer!” he exulted to colleagues at Apple when he found out.

When Plimpton threw a party for Anywhere but Here in late 1986, Jobs flew to New York to accompany Mona to it. They grew increasingly close, though their friendship had the complexities that might be expected, considering who they were and how they had come together. “Mona was not completely thrilled at first to have me in her life and have her mother so emotionally affectionate toward me,” he later said. “As we got to know each other, we became really good friends, and she is my family. I don’t know what I’d do without her. I can’t imagine a better sister. My adopted sister, Patty, and I were never close.” Mona likewise developed a deep affection for him, and at times could be very protective, although she would later write an edgy novel about him, A Regular Guy, that described his quirks with discomforting accuracy.

One of the few things they would argue about was her clothes. She dressed like a struggling novelist, and he would berate her for not wearing clothes that were “fetching enough.” At one point his comments so annoyed her that she wrote him a letter: “I am a young writer, and this is my life, and I’m not trying to be a model anyway.” He didn’t answer. But shortly after, a box arrived from the store of Issey Miyake, the Japanese fashion designer whose stark and technology-influenced style made him one of Jobs’s favorites. “He’d gone shopping for me,” she later said, “and he’d picked out great things, exactly my size, in flattering colors.” There was one pantsuit that he had particularly liked, and the shipment included three of them, all identical. “I still remember those first suits I sent Mona,” he said. “They were linen pants and tops in a pale grayish green that looked beautiful with her reddish hair.”

The Lost Father

In the meantime, Mona Simpson had been trying to track down their father, who had wandered off when she was five. Through Ken Auletta and Nick Pileggi, prominent Manhattan writers, she was introduced to a retired New York cop who had formed his own detective agency. “I paid him what little money I had,” Simpson recalled, but the search was unsuccessful. Then she met another private eye in California, who was able to find an address for Abdulfattah Jandali in Sacramento through a Department of Motor Vehicles search. Simpson told her brother and flew out from New York to see the man who was apparently their father.

Jobs had no interest in meeting him. “He didn’t treat me well,” he later explained. “I don’t hold anything against him—I’m happy to be alive. But what bothers me most is that he didn’t treat Mona well. He abandoned her.” Jobs himself had abandoned his own illegitimate daughter, Lisa, and now was trying to restore their relationship, but that complexity did not soften his feelings toward Jandali. Simpson went to Sacramento alone.

“It was very intense,” Simpson recalled. She found her father working in a small restaurant. He seemed happy to see her, yet oddly passive about the entire situation. They talked for a few hours, and he recounted that, after he left Wisconsin, he had drifted away from teaching and gotten into the restaurant business.

Jobs had asked Simpson not to mention him, so she didn’t. But at one point her father casually remarked that he and her mother had had another baby, a boy, before she had been born. “What happened to him?” she asked. He replied, “We’ll never see that baby again. That baby’s gone.” Simpson recoiled but said nothing.

An even more astonishing revelation occurred when Jandali was describing the previous restaurants that he had run. There had been some nice ones, he insisted, fancier than the Sacramento joint they were then sitting in. He told her, somewhat emotionally, that he wished she could have seen him when he was managing a Mediterranean restaurant north of San Jose. “That was a wonderful place,” he said. “All of the successful technology people used to come there. Even Steve Jobs.” Simpson was stunned. “Oh, yeah, he used to come in, and he was a sweet guy, and a big tipper,” her father added. Mona was able to refrain from blurting out, Steve Jobs is your son!

When the visit was over, she called Jobs surreptitiously from the pay phone at the restaurant and arranged to meet him at the Espresso Roma café in Berkeley. Adding to the personal and family drama, he brought along Lisa, now in grade school, who lived with her mother, Chrisann. When they all arrived at the café, it was close to 10 p.m., and Simpson poured forth the tale. Jobs was understandably astonished when she mentioned the restaurant near San Jose. He could recall being there and even meeting the man who was his biological father. “It was amazing,” he later said of the revelation. “I had been to that restaurant a few times, and I remember meeting the owner. He was Syrian. Balding. We shook hands.”

Nevertheless Jobs still had no desire to see him. “I was a wealthy man by then, and I didn’t trust him not to try to blackmail me or go to the press about it,” he recalled. “I asked Mona not to tell him about me.”

She never did, but years later Jandali saw his relationship to Jobs mentioned online. (A blogger noticed that Simpson had listed Jandali as her father in a reference book and figured out he must be Jobs’s father as well.) By then Jandali was married for a fourth time and working as a food and beverage manager at the Boomtown Resort and Casino just west of Reno, Nevada. When he brought his new wife, Roscille, to visit Simpson in 2006, he raised the topic. “What is this thing about Steve Jobs?” he asked. She confirmed the story, but added that she thought Jobs had no interest in meeting him. Jandali seemed to accept that. “My father is thoughtful and a beautiful storyteller, but he is very, very passive,” Simpson said. “He never contacted Steve.”

Simpson turned her search for Jandali into a basis for her second novel, The Lost Father, published in 1992. (Jobs convinced Paul Rand, the designer who did the NeXT logo, to design the cover, but according to Simpson, “It was God-awful and we never used it.”) She also tracked down various members of the Jandali family, in Homs and in America, and in 2011 was writing a novel about her Syrian roots. The Syrian ambassador in Washington threw a dinner for her that included a cousin and his wife who then lived in Florida and had flown up for the occasion.

Simpson assumed that Jobs would eventually meet Jandali, but as time went on he showed even less interest. In 2010, when Jobs and his son, Reed, went to a birthday dinner for Simpson at her Los Angeles house, Reed spent some time looking at pictures of his biological grandfather, but Jobs ignored them. Nor did he seem to care about his Syrian heritage. When the Middle East would come up in conversation, the topic did not engage him or evoke his typical strong opinions, even after Syria was swept up in the 2011 Arab Spring uprisings. “I don’t think anybody really knows what we should be doing over there,” he said when I asked whether the Obama administration should be intervening more in Egypt, Libya, and Syria. “You’re fucked if you do and you’re fucked if you don’t.”

Jobs did retain a friendly relationship with his biological mother, Joanne Simpson. Over the years she and Mona would often spend Christmas at Jobs’s house. The visits could be sweet, but also emotionally draining. Joanne would sometimes break into tears, say how much she had loved him, and apologize for giving him up. It turned out all right, Jobs would reassure her. As he told her one Christmas, “Don’t worry. I had a great childhood. I turned out okay.”

Lisa

Lisa Brennan, however, did not have a great childhood. When she was young, her father almost never came to see her. “I didn’t want to be a father, so I wasn’t,” Jobs later said, with only a touch of remorse in his voice. Yet occasionally he felt the tug. One day, when Lisa was three, Jobs was driving near the house he had bought for her and Chrisann, and he decided to stop. Lisa didn’t know who he was. He sat on the doorstep, not venturing inside, and talked to Chrisann. The scene was repeated once or twice a year. Jobs would come by unannounced, talk a little bit about Lisa’s school options or other issues, then drive off in his Mercedes.

But by the time Lisa turned eight, in 1986, the visits were occurring more frequently. Jobs was no longer immersed in the grueling push to create the Macintosh or in the subsequent power struggles with Sculley. He was at NeXT, which was calmer, friendlier, and headquartered in Palo Alto, near where Chrisann and Lisa lived. In addition, by the time she was in third grade, it was clear that Lisa was a smart and artistic kid, who had already been singled out by her teachers for her writing ability. She was spunky and high-spirited and had a little of her father’s defiant attitude. She also looked a bit like him, with arched eyebrows and a faintly Middle Eastern angularity. One day, to the surprise of his colleagues, he brought her by the office. As she turned cartwheels in the corridor, she squealed, “Look at me!”

Avie Tevanian, a lanky and gregarious engineer at NeXT who had become Jobs’s friend, remembers that every now and then, when they were going out to dinner, they would stop by Chrisann’s house to pick up Lisa. “He was very sweet to her,” Tevanian recalled. “He was a vegetarian, and so was Chrisann, but she wasn’t. He was fine with that. He suggested she order chicken, and she did.”

Eating chicken became her little indulgence as she shuttled between two parents who were vegetarians with a spiritual regard for natural foods. “We bought our groceries—our puntarella, quinoa, celeriac, carob-covered nuts—in yeasty-smelling stores where the women didn’t dye their hair,” she later wrote about her time with her mother. “But we sometimes tasted foreign treats. A few times we bought a hot, seasoned chicken from a gourmet shop with rows and rows of chickens turning on spits, and ate it in the car from the foil-lined paper bag with our fingers.” Her father, whose dietary fixations came in fanatic waves, was more fastidious about what he ate. She watched him spit out a mouthful of soup one day after learning that it contained butter. After loosening up a bit while at Apple, he was back to being a strict vegan. Even at a young age Lisa began to realize his diet obsessions reflected a life philosophy, one in which asceticism and minimalism could heighten subsequent sensations. “He believed that great harvests came from arid sources, pleasure from restraint,” she noted. “He knew the equations that most people didn’t know: Things led to their opposites.”

In a similar way, the absence and coldness of her father made his occasional moments of warmth so much more intensely gratifying. “I didn’t live with him, but he would stop by our house some days, a deity among us for a few tingling moments or hours,” she recalled. Lisa soon became interesting enough that he would take walks with her. He would also go rollerblading with her on the quiet streets of old Palo Alto, often stopping at the houses of Joanna Hoffman and Andy Hertzfeld. The first time he brought her around to see Hoffman, he just knocked on the door and announced, “This is Lisa.” Hoffman knew right away. “It was obvious she was his daughter,” she told me. “Nobody has that jaw. It’s a signature jaw.” Hoffman, who suffered from not knowing her own divorced father until she was ten, encouraged Jobs to be a better father. He followed her advice, and later thanked her for it.

Once he took Lisa on a business trip to Tokyo, and they stayed at the sleek and businesslike Okura Hotel. At the elegant downstairs sushi bar, Jobs ordered large trays of unagi sushi, a dish he loved so much that he allowed the warm cooked eel to pass muster as vegetarian. The pieces were coated with fine salt or a thin sweet sauce, and Lisa remembered later how they dissolved in her mouth. So, too, did the distance between them. As she later wrote, “It was the first time I’d felt, with him, so relaxed and content, over those trays of meat; the excess, the permission and warmth after the cold salads, meant a once inaccessible space had opened. He was less rigid with himself, even human under the great ceilings with the little chairs, with the meat, and me.”

But it was not always sweetness and light. Jobs was as mercurial with Lisa as he was with almost everyone, cycling between embrace and abandonment. On one visit he would be playful; on the next he would be cold; often he was not there at all. “She was always unsure of their relationship,” according to Hertzfeld. “I went to a birthday party of hers, and Steve was supposed to come, and he was very, very, late. She got extremely anxious and disappointed. But when he finally did come, she totally lit up.”

Lisa learned to be temperamental in return. Over the years their relationship would be a roller coaster, with each of the low points elongated by their shared stubbornness. After a falling-out, they could go for months not speaking to each other. Neither one was good at reaching out, apologizing, or making the effort to heal, even when he was wrestling with repeated health problems. One day in the fall of 2010 he was wistfully going through a box of old snapshots with me, and paused over one that showed him visiting Lisa when she was young. “I probably didn’t go over there enough,” he said. Since he had not spoken to her all that year, I asked if he might want to reach out to her with a call or email. He looked at me blankly for a moment, then went back to riffling through other old photographs.

The Romantic

When it came to women, Jobs could be deeply romantic. He tended to fall in love dramatically, share with friends every up and down of a relationship, and pine in public whenever he was away from his current girlfriend. In the summer of 1983 he went to a small dinner party in Silicon Valley with Joan Baez and sat next to an undergraduate at the University of Pennsylvania named Jennifer Egan, who was not quite sure who he was. By then he and Baez had realized that they weren’t destined to be forever young together, and Jobs found himself fascinated by Egan, who was working on a San Francisco weekly during her summer vacation. He tracked her down, gave her a call, and took her to Café Jacqueline, a little bistro near Telegraph Hill that specialized in vegetarian soufflés.

They dated for a year, and Jobs often flew east to visit her. At a Boston Macworld event, he told a large gathering how much in love he was and thus needed to rush out to catch a plane for Philadelphia to see his girlfriend. The audience was enchanted. When he was visiting New York, she would take the train up to stay with him at the Carlyle or at Jay Chiat’s Upper East Side apartment, and they would eat at Café Luxembourg, visit (repeatedly) the apartment in the San Remo he was planning to remodel, and go to movies or (once at least) the opera.

He and Egan also spoke for hours on the phone many nights. One topic they wrestled with was his belief, which came from his Buddhist studies, that it was important to avoid attachment to material objects. Our consumer desires are unhealthy, he told her, and to attain enlightenment you need to develop a life of nonattachment and non-materialism. He even sent her a tape of Kobun Chino, his Zen teacher, lecturing about the problems caused by craving and obtaining things. Egan pushed back. Wasn’t he defying that philosophy, she asked, by making computers and other products that people coveted? “He was irritated by the dichotomy, and we had exuberant debates about it,” Egan recalled.

In the end Jobs’s pride in the objects he made overcame his sensibility that people should eschew being attached to such possessions. When the Macintosh came out in January 1984, Egan was staying at her mother’s apartment in San Francisco during her winter break from Penn. Her mother’s dinner guests were astonished one night when Steve Jobs—suddenly very famous—appeared at the door carrying a freshly boxed Macintosh and proceeded to Egan’s bedroom to set it up.

Jobs told Egan, as he had a few other friends, about his premonition that he would not live a long life. That was why he was driven and impatient, he confided. “He felt a sense of urgency about all he wanted to get done,” Egan later said. Their relationship tapered off by the fall of 1984, when Egan made it clear that she was still far too young to think of getting married.

Shortly after that, just as the turmoil with Sculley was beginning to build at Apple in early 1985, Jobs was heading to a meeting when he stopped at the office of a guy who was working with the Apple Foundation, which helped get computers to nonprofit organizations. Sitting in his office was a lithe, very blond woman who combined a hippie aura of natural purity with the solid sensibilities of a computer consultant. Her name was Tina Redse. “She was the most beautiful woman I’d ever seen,” Jobs recalled.

He called her the next day and asked her to dinner. She said no, that she was living with a boyfriend. A few days later he took her on a walk to a nearby park and again asked her out, and this time she told her boyfriend that she wanted to go. She was very honest and open. After dinner she started to cry because she knew her life was about to be disrupted. And it was. Within a few months she had moved into the unfurnished mansion in Woodside. “She was the first person I was truly in love with,” Jobs later said. “We had a very deep connection. I don’t know that anyone will ever understand me better than she did.”

Redse came from a troubled family, and Jobs shared with her his own pain about being put up for adoption. “We were both wounded from our childhood,” Redse recalled. “He said to me that we were misfits, which is why we belonged together.” They were physically passionate and prone to public displays of affection; their make-out sessions in the NeXT lobby are well remembered by employees. So too were their fights, which occurred at movie theaters and in front of visitors to Woodside. Yet he constantly praised her purity and naturalness. As the well-grounded Joanna Hoffman pointed out when discussing Jobs’s infatuation with the otherworldly Redse, “Steve had a tendency to look at vulnerabilities and neuroses and turn them into spiritual attributes.”

When he was being eased out at Apple in 1985, Redse traveled with him in Europe, where he was salving his wounds. Standing on a bridge over the Seine one evening, they bandied about the idea, more romantic than serious, of just staying in France, maybe settling down, perhaps indefinitely. Redse was eager, but Jobs didn’t want to. He was burned but still ambitious. “I am a reflection of what I do,” he told her. She recalled their Paris moment in a poignant email she sent to him twenty-five years later, after they had gone their separate ways but retained their spiritual connection:

We were on a bridge in Paris in the summer of 1985. It was overcast. We leaned against the smooth stone rail and stared at the green water rolling on below. Your world had cleaved and then it paused, waiting to rearrange itself around whatever you chose next. I wanted to run away from what had come before. I tried to convince you to begin a new life with me in Paris, to shed our former selves and let something else course through us. I wanted us to crawl through that black chasm of your broken world and emerge, anonymous and new, in simple lives where I could cook you simple dinners and we could be together every day, like children playing a sweet game with no purpose save the game itself. I like to think you considered it before you laughed and said “What could I do? I’ve made myself unemployable.” I like to think that in that moment’s hesitation before our bold futures reclaimed us, we lived that simple life together all the way into our peaceful old ages, with a brood of grandchildren around us on a farm in the south of France, quietly going about our days, warm and complete like loaves of fresh bread, our small world filled with the aroma of patience and familiarity.

The relationship lurched up and down for five years. Redse hated living in his sparsely furnished Woodside house. Jobs had hired a hip young couple, who had once worked at Chez Panisse, as housekeepers and vegetarian cooks, and they made her feel like an interloper. She would occasionally move out to an apartment of her own in Palo Alto, especially after one of her torrential arguments with Jobs. “Neglect is a form of abuse,” she once scrawled on the wall of the hallway to their bedroom. She was entranced by him, but she was also baffled by how uncaring he could be. She would later recall how incredibly painful it was to be in love with someone so self-centered. Caring deeply about someone who seemed incapable of caring was a particular kind of hell that she wouldn’t wish on anyone, she said.

They were different in so many ways. “On the spectrum of cruel to kind, they are close to the opposite poles,” Hertzfeld later said. Redse’s kindness was manifest in ways large and small; she always gave money to street people, she volunteered to help those who (like her father) were afflicted with mental illness, and she took care to make Lisa and even Chrisann feel comfortable with her. More than anyone, she helped persuade Jobs to spend more time with Lisa. But she lacked Jobs’s ambition and drive. The ethereal quality that made her seem so spiritual to Jobs also made it hard for them to stay on the same wavelength. “Their relationship was incredibly tempestuous,” said Hertzfeld. “Because of both of their characters, they would have lots and lots of fights.”

They also had a basic philosophical difference about whether aesthetic tastes were fundamentally individual, as Redse believed, or universal and could be taught, as Jobs believed. She accused him of being too influenced by the Bauhaus movement. “Steve believed it was our job to teach people aesthetics, to teach people what they should like,” she recalled. “I don’t share that perspective. I believe when we listen deeply, both within ourselves and to each other, we are able to allow what’s innate and true to emerge.”

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. “Though our values clashed 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.