On our third date, he gave me a mixtape he’d made for me. It was an actual cassette. I had to borrow a friend’s 20-year-old Walkman just to listen to it, but I could tell from the handwritten inlay card that the content wasn’t subtle. It opened with the Ramones’ “I Wanna Be Your Boyfriend,” and it ended with “Let’s Get It On.” That night he asked me to “be his girl”; he said he was tired of playing the field. We barely knew each other, and yet there he was, asking me to go steady like we were teenagers in a 1950s high school musical rather than 30-year-olds who’d recently met on the internet. I was dazed and very flattered, so I went along with it and said yes. I don’t remember if we kissed immediately afterward, although certainly every social, literary, and cinematic cue would dictate that we should have. But you never knew with him. After such overt dialogue, he was prone to retreat. I hope I at least tried to hold his hand, and I hope he let me.
I tolerated his eccentricities in part because he was a rock star. Okay, he wasn’t quite a rock star. He was a semi-famous-in-some-circles musician who’d written one truly great love song. And a few other decent ones. And 80 or so not-so-decent ones, but who cared? He was cute — dreamy, really — and in some lights he was even romantic, especially if you ignored his theories about 9/11 and the way he fidgeted in his chair when you tried to tell him about your day. It was as if he saved up all of his confidence for his blustery onstage persona, so that one-on-one he was quiet, tense. He could say sweet things like he’d memorized them for a rom-com screenplay, but he had trouble making eye contact. He was Peter Kavinsky with an anxiety disorder.
Our next date was scheduled for a freezing night. He was nervous — he was always nervous, but that night, in particular, I wanted to Xanax him. He, being someone who hated sitting in bars, where it was warm and cozy and stocked with tension-relieving booze, suggested we take a walk. I bundled up and went along with it, in the name of adventure and because he seemed so earnestly excited. We walked the Brooklyn Heights Promenade and into a park in Dumbo. We eventually arrived at a lookout spot that seemed to be smack dab in the middle of the East River, directly beneath the Manhattan and Brooklyn Bridges. New York seemed large and small at the same time, the vastness of the scenery tempered by the feeling that if I reached out my arm I could touch the lights that twinkled from buildings all around us. It felt like we were the only two people in the city, and for a moment the possibilities were endless: for New York, for the night, for us.
So we stood there a while. And we, uh, chatted? He asked a mundane question about work (I fascinated him because I had a day job and an apartment I leased in my own name). And then we fell silent. I told myself we were letting the surrounding beauty wash over us. And then we … sorta just stood there? I waited for some wonderful cliché to envelop us: fireworks, or symphonies, or maybe just a kiss — anything could happen, then and there. But nothing happened, except the sense that perhaps I was starting to lose feeling in my toes. Even the sight of him in his cool leather jacket couldn’t keep me warm. So then we, uh, chatted some more.
“It’s actually pretty chilly!”
“Eh, it’s okay.”
“Yeah. But maybe we should get going.” And so we walked away.
Later that night he told me that his original intent was to bring a boombox with him and to serenade me with a love song right there, at the foot of the Brooklyn Bridge. He’d chickened out, and that was why there was so much awkward conversation and no action. Frankly, I was relieved. I’d grown up loving musicals in which a starry-eyed young man might interrupt dialogue and break into song in order to express his feelings for a lady. She would respond by singing along with him, or tap dancing or doing something equally adorable to convey her mutual feelings. Instant intimacy could be achieved with nothing but vocal harmony and a good sense of rhythm.
But in real life, I don’t know if I’m the kind of woman who could ever have a conventionally appropriate response to a serenade. I’d be too busy giggling, if not flat-out running away in the opposite direction toward the safety of a karaoke booth. We hadn’t known each other long enough for him to intuit this — or, really, anything at all — about me. We dated for another lackluster month or two, but I don’t think we ever got to know each other any better. Eventually the scale tipped fully toward “awkward”; “charming” had lost out. I didn’t care that his great big, straight-from-a-rom-com ideas never quite translated into reality. It was more his lack of patience for the ordinary, the offstage times when life offers only mundane views and very little music. The sitting-in-front-of-the-TV in sweatpants times. New York has so many glorious vantage points that never fail to make me swoon, but the view from my couch? That’s the one that really matters.