Spring evenings in New York City can be magic. Sometimes a lingering winter chill will settle in just after dark, but I remember one Tuesday in April1 2010 as particularly spectacular: The air was cool instead of cold, carrying the first hint of a thaw, and it was crystalline—the better to watch the sun set from the window of my cab headed downtown. I was wearing a glen plaid blazer, one I’d settled on just an hour earlier after a half day of indecision. I remember these details so well because that evening was the first time I met the woman who would become my wife.
But not exactly the first time. Maybe I fretted over the details because she first laid eyes on me on a computer screen, the two of us introduced via Match.com2 profiles. In fairness, I was steering the dating site’s algorithm a bit: Even though I lived in San Francisco, I had tweaked my zip code to the New York City address where I stayed when in town on business. So after our initial digital introductions (a Favorite from her, a message3 from me, calls and then texts and then emails), we decided to meet in person. I wondered whether the reality would live up to the virtual—never a sure thing. In Amy’s case, reality did much, much better.
We had arranged to meet for dinner at Gramercy Tavern. I pushed through the crowd always clustered in the foyer and, scanning the bar, immediately recognized the glossy sable curls I knew from her profile. She was wearing a black leather jacket and dark jeans4, and she was on her cell. A second later, she turned around, still on the phone, and looked toward the door. As she recognized me, she smiled. I made my way over and heard her tell her mom5 she’d call back later.
Weeks earlier, when I had seen Amy’s photographs on Match, I had been instantly smitten, but in person she was even more phenomenal. She gave me a hug, and we exchanged pleasantries. She smelled wonderful, like morning light. I was suddenly feeling very nervous. Mediated by screens and keyboards, I’d been able to finely calibrate my so-called charm. But now, face-to-face, the technology couldn’t help me.
We sat down and worked through the first date punch list: jobs, friends (drink orders), interests, favorite travels (menu selections), exes, families, hobbies. Most of it we already knew from our online profiles, honestly. But now that all seemed unacceptably low-resolution. I lose some command of detail here because time sped up so profoundly, a blur of listening, talking, and laughing. Before I knew it, we were demolishing an insane cherry brown butter cake6 while I worked on schemes to get this amazing woman to see me again. Outside, I hailed Amy a cab and put her in it. I can’t remember if I asked to see her again, because my heart was pounding out of my chest and my brain was imploring me—begging me—to kiss her good-night. But I was petrified of being too forward, so I didn’t, and as I waved good-bye, a group of four drunk Wall Street bankers started yelling at me. “Kiss her, you idiot! What the hell is wrong with you!” and “Oh man! You blew it!”—followed by catcalls and laughter.
Thirty seconds7 later I turned to technology once more, breaking a basic rule: I texted her. But she answered. And we made plans to walk the High Line that Saturday afternoon. Guess what? I kissed8 her, not even an hour into our second date.