Rooftop Redemption at the Windermere Hotel



666 W End Ave, NY, NY 10025

Neighborhood: Upper West Side

I had come to New York for spring break in search of fixing a broken heart. Probably a silly reason, but the cause and focus of that broken heart was spending the semester in New York at the Hotel Windermere with other theater students from my college in Indiana. Why I thought I could patch things up I’ll never know. Besides, I was a 20-year-old gay boy from the Midwest and what better place to fix a broken heart than New York City. After a cramped overnight drive, I fell out of a friends car onto the sidewalk in front of the Upper West Side hotel.

The Windermere’s days as a hotel, however, had long passed. The sidewalk along West End Avenue was empty, silent in the early morning sun. A dreary lobby dotted with ancient residents who sat motionless in ratty furniture served as my welcoming committee. I stood motionless in the gloom, unsure what to do next. But soon, a couple of friends from school appeared, summoned somehow by a silent wish, and piled me into an elevator. They hauled me upstairs to rooms that seemed to be nothing more than wall-to-wall beds, which I would learn as the week passed, were hardly ever slept in. The man I’d come to see was, of course, nowhere to be found. I swallowed my disappointment, stowed my things, and escaped back out to the street.

It was just a block over to Broadway. Unlike the Windermere, everything seemed alive on the street, running at a speed 10 times that of my normal life. Smells of exhaust mixed with food, dust, rain, and perfume. Galleries, movie houses, waves of bodies pressing into subway cars that rumbled underneath my feet. For three days, I was in sensory overload, and Mr. Break-My-Heart ignored me. Totally.

But his roommate didn’t, a tall, boyish actor who I’d met before back at school. Paul, another small-town Indiana boy who took to New York for all he was worth. Auditions, meetings with agents, small plays here and there, waiting jobs-he was infused with Manhattan and would never be coming home again. When I first arrived, I hardly noticed him, but he seemed genuinely happy about my visit, unlike Mr. Break-My-Heart. By midweek, he began to show up more frequently, finding excuses to walk with me into the city, or joining a couple of friends and me for dinner and club outings.

He was an enthusiastic flirt, and, catching me totally off guard, would stare at me until I blushed. Then he would make a face and break into broad laughter. I couldn’t decide whether to be annoyed or amused. Riding the subway, he would press his knee against mine, or if we were standing, a slight rock of the car somehow resulted in a full body press. I had become his mission. He latched on to me and through the week flirted, cajoled, basically hounded me to go out one evening to forget Mr. Break-My-Heart and focus on the city and on him. I resisted, as anyone reveling in the pain of a broken heart can, but he was nothing if not persistent. I finally relented. A dinner, a date with Paul. What we ate, what we said, and where we walked is long gone from memory, but at the end of the evening, back at the Windermere, Paul took my hand and pulled me up several flights of stairs, drawing me higher and higher until we burst through a door into the cold night, lights glowing like a kaleidoscope all around us, stars faint overhead. He wanted to kiss me, he said, there on the roof. And he did, a warm, soft kiss to make me forget the sharp wind stinging my face. To make me forget Mr. Break-My-Heart. I turned and we stood pressed together, him with his long arms wrapping me up, looking out at the lights and up at the sky. Without warning, a shooting star-I swear to God-shot through the sky. Not one of those little, quick dashes of light. No, this was a huge sparkling thing, throwing off stardust as it arched overhead then vanished. See, he said, it’s a sign; you were supposed to come out with me.

Paul died a long time ago, very young, maybe not so talented but full of belief that he was. The tiny spark of him that I knew stays with me in that memory of a roof, a kiss, and a shooting star. I never talked to Mr. Break-My-Heart again.

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