It was dark out when Michael Jackson climbed into Madonna’s car, and his sunglasses were still on. He’d turned up at her house alone. There were no bodyguards and no driver, just the two biggest pop stars of the 1980s heading to a restaurant with Madonna at the wheel.
The dinner was her idea. “In 1991 I decided I wanted to try and get to know him better,” she said on stage at the MTV Video Music Awards in New York in September 2009. “I asked him out to dinner. I said, my treat, I’ll drive, just you and me.” He agreed.
The same year, the two of them walked into the Academy Awards together. On March 25, 1991, Madonna arrived at the Shrine Auditorium in Los Angeles in a white beaded Bob Mackie gown, a nod to Marilyn Monroe, with Harry Winston diamonds reportedly worth $20 million. She held Michael’s gloved hand down the press line. That night she sang “Sooner or Later,” Stephen Sondheim’s song from “Dick Tracy,” and it won the Oscar for best original song.
A red carpet is loud, though. A dinner for two isn’t, and in the quiet of the car the sunglasses were hard to ignore. Madonna couldn’t see his eyes, and she wasn’t shy about saying so.
“I said, Michael, I feel like I’m talking to a limousine,” she told the VMA crowd. Then she asked him straight out: “Do you think you could take off those glasses so I can see your eyes?”
Madonna tells the story on stage at the 2009 MTV VMAs
This is a fan upload of the 2009 TV broadcast with subtitles, not an official MTV copy. Madonna starts the dinner story at about 2:37, and the sunglasses moment runs from 2:45 to 3:10.
Michael took a second before he answered. “He paused for a moment,” Madonna said, “then he tossed the glasses out the window, looked at me with a wink and a smile and said, can you see me now, is that better?”
Just like that, the King of Pop was sitting in her passenger seat with nothing between his eyes and hers.
That set the tone for the rest of the meal. Madonna said she was “hellbent” on getting him to eat French fries, drink wine and have dessert, all of them “things he never seemed to allow himself to do.” She wanted the shy superstar to loosen up for one night.
They didn’t end the evening at the restaurant. “Later we went back to my house to watch a movie and sat on the couch like two kids,” she said. “Somewhere in the middle of the movie, his hand snuck over and held mine.”
She didn’t make it sound like a grand love story. “It felt like he was looking for more of a friend than a romance, and I was happy to oblige,” she said. What she remembered was a man who had shown up without his security and, for one dinner at least, without his famous shades.
Nearly three decades later Madonna went back to that spring in a post on Instagram. She shared photos of the two of them from Oscars night, Michael in white with his hair loose and Madonna in platinum curls, and captioned it “Best Date Ever!”