Six months later, in February, 1943, most of the men Jack sailed with that summer—including Glory and the pastry chef—were killed when the Dorchester was torpedoed by a German U-boat. More than six hundred people died. Jack was so shattered by the news that his hands shook for weeks afterward. I remember him wearing the leather jacket even after he became famous and could have afforded a new one. I wonder if it reminded him of what Buddhists call the void. We were all heading there, he told me more than once, though he knew I didn’t like to hear about that.

The week before our blind date, Jack’s previous girlfriend had thrown him out of her apartment, on the advice of her psychiatrist, so he was in serious need of a place to stay, as he had often been during his travels. Since I happened to be a young woman with an apartment of her own—something of a rarity in those days—Allen Ginsberg, whom I’d recently got to know, had arranged for us to meet. My two haphazardly furnished rooms were in a brownstone a couple of blocks from Columbia. The windows looked out on a back yard where generations of bedsprings rusted and a tree of heaven grew. Just before we stepped inside, he pulled me close and kissed me. “I don’t like blondes,” he murmured, which I thought was too ridiculous to take seriously. By the time we’d left the subway and his arm dropped around me as we walked along Broadway, it was clear that we were going to be friends, whatever else we might be to each other.

I had just survived a bad breakup and a really awful year, which should have made me cautious. Instead, I had a nothing-to-lose feeling. The next day, Jack moved into my apartment with a zippered sports bag that he picked up from the cheap hotel on Eighth Street where he’d been staying. It contained a notebook and a couple of changes of clothes, mostly from the Salvation Army.

I knew he’d be leaving as soon as he got his first five-hundred-dollar check for “On the Road,” which Viking Press was finally going to publish after three years of maddening indecision. Still, by the time Jack boarded a freighter, six weeks later, it was hard to say goodbye. I remember trying not to show it, because I knew he didn’t want to carry any weight as he moved through the world. When I began writing him letters full of news about my life in New York, I hesitated before typing “Love” above my name.

We spent our last night together in Jack’s cabin aboard the S.S. Slovenia. It was an experience he wanted me to have—he knew I was afraid my life would never give me enough to write about, and he’d been urging me to do some travelling of my own. The ship was still docked in Brooklyn, but I could feel the cabin gently rocking as the East River moved under us. Early the next morning, as I walked to the subway through the Brooklyn Navy Yard, Jack was on his way to Tangier, to visit William Burroughs. From there he would go to Paris, where he was thinking about living for the rest of his life.

He’d forgotten to pack his red-and-black shirt. I hung it in the closet, wondering if I’d see him again. Three weeks later, I opened my mailbox and found a letter. “We had a tremendous storm 500 miles out & almost foundered,” Jack wrote. He was currently eight miles off the coast of Africa, looking forward to landing in Tangier, “the Blue Pearl of the Hesperides—the city of vice!” He told me that he’d spent the voyage studying history and reading Kierkegaard in his cabin and that, since he hadn’t been drinking, he was now the healthy Jack I’d never known. “We’ll meet again,” he promised.

In his next letter, he wrote about walking through the casbah, the “whanging music” he heard, the cafés where marijuana was smoked openly. It sounded like the kind of adventure he’d imagined. But two weeks later he was wishing he hadn’t come—too many “dull expatriate characters” and “not too many good vibrations.” “Lonely here,” he wrote. “Don’t like whores anyway and no girls speak English.” Had he forgotten to whom he was writing? Or was it that he felt there was nothing he couldn’t tell me?