All the photos from that night showed us looking in different directions, my body stiff and an awkward smile plastered on my face. There was nothing to smile about. Quite honestly, I was afraid to smile in most photographs, as I’d been told as a little girl that my nose was too wide and smiling made it spread more. That shot of insecurity was followed by a chaser from Sony’s artist development executive, a rotund and imposing lady who told me when we first met, before my first record: “This is your flattering side. You should only ever be photographed on this side of your face.” (It was the side without the beauty mark. Who are these people? Who. Are. They?)
I was too young and didn’t have the confidence to challenge her opinion, so I obeyed. I internalized so many of the damaging and cruel critiques older people had given me as a child and young woman; some have burrowed so deep down in my psyche that I will never be able to root them out entirely. To this day I unconsciously turn to the “flattering side” if there is a camera around; it’s a thing.
The gala was your typical celebrity-studded chicken-dinner charity event. I sat up straight, sucked in my stomach, and held my breath until it was over. Tommy and I faked it all night without incident. We both had quite a bit of practice in faking it. Then it was over: I had given Tommy his public moment, and now I was free to go! This was a big friggin’ deal! I was never allowed to go anywhere social without him. I couldn’t believe it! I was free to laugh and have fun, like a human being, without being shushed and silenced and sequestered. I felt kind of like Cinderella in reverse; it was the fancy ball that was the chore.
In the 1990s, Giorgio Armani was the pinnacle of a luxury fashion house. Armani was the go-to designer of all the A-listers. Tommy, of course, wore Armani and he was always trying to class it up. And I occasionally wore Armani too. There were several cool and connected people who worked for the designer and hung out with their cool clients. After the gala, our plan was to go to a dinner party at a restaurant that some of the Armani insiders had arranged. My assistant and I went, and Wanya met us there. It was a fab downtown scene.
The lighting in the place was low, and twenty of us were seated in the back against a gigantic wall of windows, around a large dining table crowded with beautiful bottles of wine and candles. The air was electric with playful chatter and laughter. And there was great music playing in the background, with Wanya occasionally breaking out into riffs. It was an ordinary night to everyone else there, but it was a revelation to me, being out socially with my peers and listening to the music of my time.
Though I was still being watched, I felt lighter than I had in a long time. I felt young and unchained. It was not uncommon for a dinner party of this kind to have guests come and go in waves, so when Derek Jeter and his friend came in and sat down across from me at the table, they didn’t command any of my attention. I found them both ambiguous. After I briefly glanced up at them I thought, Who are these guys? my attention went right back to the more interesting dinner guests.
I was never drawn to the jock type, not even in high school, where athletes were at the top of the food chain. Derek and his friend were no exception to my rule. His Armani suit didn’t cover up the Kalamazoo in him. He didn’t have the New York slick vibe that I had become so accustomed to. I’m not being shady, but he had on pointy shoes. Artists can be very tribal, and compared to the hip-hop and R & B stars, models, fashionistas, and cool kids in every hue at the table, the two of them presented as rather pedestrian.
The restaurant was moody, but our table was buzzing, and at some point the conversation moved to “inconspicuous Blackness”—passing, but with more nuance. I was riveted. We discussed who we thought was secretly Black or else could have some Black running through them, how they might or might not identify and how they were often misidentified. I had never had an open conversation about biracial or multiracial aesthetics, ever. My parents didn’t have the language for it, and Tommy never wanted to talk about my biracial identity; if he wasn’t ashamed of it, he certainly didn’t want to promote it. I couldn’t believe it: it was my first night out without him, and suddenly I was in a dialogue about race and identity with young, smart, and creative people!
Eventually the debate turned to me. One of the guys from Armani said he couldn’t tell if I was part Black (no parts of him were Black, by the way). Wanya wasn’t having it. His voice got up in his high register: “Naw, man, come on! We all know; how could you not know?” I was laughing, but I was also deeply interested.
As if on cue, another person from the Armani team chimed in, “Derek, your mother’s Irish and your dad’s Black, right? Like, so what do you think about all this?”
All of a sudden, it was like the moment in The Wizard of Oz when the screen went from black-and-white to Technicolor. I was in a new moment, a new room; it was a new night and perhaps a new world. When I heard “Irish mother and Black father,” my
