“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.”