Adapted from Barack Obama: The Story, by David Maraniss, to be published this month by Simon & Schuster; © 2012 by the author.

Barack Obama transferred from Occidental College to Columbia University in 1981, his junior year. Although he left Los Angeles with enough ambitious propulsion to carry him into a more active period, he instead receded into the most existentialist stretch of his life. As he put it himself dec­ades later during an interview in the Oval Office, “I was leading a very ascetic existence, way too serious for my own good.” In most outward ways, compared with what had come before, his life in New York was a minimalist one, without the sprawling cast of characters that had surrounded him at Oxy and in Hawaii and Indonesia. He felt no attachment to Columbia or to the first jobs he landed after graduation. But it would be a misreading to say that he was tamping down his ambitions during that period. Just the opposite, in fact. If anything, his sense of destiny deepened. He was conducting an intense debate with himself over his past, pres­ent, and future, an internal struggle that he shared with only a few close friends, including his girlfriends, Alex McNear and Genevieve Cook, who kept a lasting rec­ord, one in letters, the other in her journal.

“Where Am I Going?”

It is exponentially easier to look back at a life than to live it forward. In retrospect it becomes apparent that New York was crucial to Obama. If he had not quite found his place yet, he was learning in which directions not to go and how to avoid turns that would lead him off the path and into traps from which it would be hard to escape. Even when he was uncertain about much else, Obama seemed hyper-alert to avoiding a future he did not want.

At age 20, Obama was a man of the world. He had never been to south-central Kansas or western Kenya, the homelands of his ancestors, yet his divided heritage from Africa and the American heartland had defined him from the beginning. He could not be of one place, rooted and provincial. From his years living in Indonesia, where he was fully immersed in Javanese schools and culture; from his adolescence in Hawaii, where he was in the polyglot sea of hapa and haole, Asians and islanders; from his mother’s long-term commitment to development work overseas; from his friendship with Pakistani students at Occidental and his extended visit to their country—from all of these he had experienced far more global diversity than the average college junior. He knew the ways of different cultures better than he knew himself.

Obama’s first apartment in New York, which he shared with Phil Boerner, a friend from Oxy, was at 142 West 109th Street. Heat and hot water were scarce commodities. When the nights turned colder, the roommates took to sleeping bags for warmth and spent as little waking time in the apartment as possible, holing up in Butler Library, at 114th, parts of which were open all night. Some mornings, eager to flee their quarters, they walked to the corner of Broadway and 112th to eat at Tom’s Restaurant, the place immortalized later as the fictional Monk’s, a familiar meeting place for the characters on Seinfeld. A full breakfast went for $1.99.

The loneliness of Obama’s New York existence emerged in his letters to Alex McNear, a young woman from Occidental who had enchanted Obama when she was co-editing the literary magazine Feast, and with whom he reconnected when she spent the summer of 1982 in New York. Alex had always been fond of Barry, as she called him, and “thought he was interesting in a very particular way. He really worked his way through an idea or question, turned it over, looked at it from all sides, and then he came to a precise and elegant conclusion.” When Alex came to New York, she gave Obama a call. They met at an Italian restaurant on Lexington Avenue, and, as she remembered the night, “we sat and talked and ate and drank wine. Or at least I drank wine. I think he drank something stronger. It was one of those dark, old Italian restaurants that don’t exist in New York anymore. It was the kind of place where they leave you alone. I remember thinking how happy I felt just talking to him, that I could talk to him for hours. We walked slowly back to my apartment, on 90th, and said good-bye. After that we started spending much more time together.”

Alex remembered it as a summer of walking miles through the city, lingering over meals at restaurants, hanging out at their apartments, visiting art museums, and talking about life. She recalled one intense conversation in particular as they stood outside the Metropolitan Museum of Art. Obama was obsessed with the concept of choice, she said. Did he have real choices in his life? Did he have free will? How much were his choices circumscribed by his background, his childhood, his socio-economic situation, the color of his skin, the expectations that others had of him? How did choice influence his pres­ent and future? Later, referring back to that discussion, he told Alex in a letter that he had used the word “choice” “as a convenient shorthand for the way my past resolves itself. Not just my past, but the past of my ancestors, the planet, the universe.” His obsession with the concept of choice, he said in a later interview at the White House, “was a deliberate effort on my part to press the pause button, essentially, and try to orient myself and say, ‘Okay, which way, where am I going?’ ”

The long-distance relationship with Alex McNear after that summer—they would drift apart as time wore on—was conducted mostly through a series of passionate letters sent between his apartment (he was then living at 339 East 94th, in Manhattan) and hers, at 2210 Ridgeview Avenue, in Eagle Rock, California. By her account, the passion was as much about ideas and words as about their romance—what she later called “that dance of closeness through language.” Alex was interested in postmodern literary criticism, and her arguments brimmed with the deconstructionist ideas of Jacques Derrida, the French philosopher. In one letter she told Obama that she was writing a paper in her modern-poetry class at Occidental about T. S. Eliot’s “The Waste Land.” His reply wove its way through literature, politics, and personal philosophy:

I haven’t read “The Waste Land” for a year, and I never did bother to check all the footnotes. But I will hazard these statements—Eliot contains the same ecstatic vision which runs from Münzer to Yeats. However, he retains a grounding in the social reality/order of his time. Facing what he perceives as a choice between ecstatic chaos and lifeless mechanistic order, he accedes to maintaining a separation of asexual purity and brutal sexual reality. And he wears a stoical face before this. Read his essay on Tradition and the Individual Talent, as well as Four Quartets, when he’s less concerned with depicting moribund Europe, to catch a sense of what I speak. Remember how I said there’s a certain kind of conservatism which I respect more than bourgeois liberalism—Eliot is of this type. Of course, the dichotomy he maintains is reactionary, but it’s due to a deep fatalism, not ignorance. (Counter him with Yeats or Pound, who, arising from the same milieu, opted to support Hitler and Mussolini.) And this fatalism is born out of the relation between fertility and death, which I touched on in my last letter—life feeds on itself. A fatalism I share with the western tradition at times. You seem surprised at Eliot’s irreconcilable ambivalence; don’t you share this ambivalence yourself, Alex?

He was trying to find his place in the whirl of humanity, while at the same time refining the literary riffs that filled up page after page of his journals. Here’s a passage from another section of that same letter: