In the spring of 1999, I was finally dipping a toe in the dating pool. The water wasn’t exactly warm. A friend had fixed me up with one of her Connecticut neighbors, and we made plans to meet for lunch. I waited. And waited. After an hour, I asked the waiter if I had waited long enough. He said yes. （I was a little out of practice.）
Wow, stood up. Why should I be any different from single women everywhere? Still, it was pretty jarring. That afternoon, my AWOL date called and apologized, explaining to my assistant that he’d been playing with his dog on his bed and fell asleep. I was more perplexed than pissed. “Is that what they’re calling it these days?” I said.
Then a podiatrist friend set me up with an anesthesiologist named Arnie, telling me he was terrific. Okay, why not?
With some trepidation I walked into the Upper East Side hot spot Coco Pazzo and scanned the crowd, feeling a few diners staring at me, perhaps curious about whom I was meeting. After a few excruciating minutes, an attractive man approached. “Hi, Katie!”
“Hi!” I said. “You must be Arnie the anesthesiologist!”
“No, actually, I’m Dave the investment banker. Arnie couldn’t make it.”
Talk about a bait and switch. Dave the investment banker seemed nice enough. Then he told me that before he and his wife called it quits, she threw all of his belongings out a second-story window. Check, please.
There was also the plastic surgeon who reeked of private-school privilege. When word got around that I was seeing him, people started coming out of the woodwork with stories; items popped up in gossip columns about rough stuff in a previous relationship that involved the cops. Some woman even asked my sister Emily to forward a letter she’d written saying she was deeply concerned about the company I was keeping. I decided it just wasn’t worth the free Botox.
Because of my job, dating was complicated. Whoever I got involved with would require not only my parents’ approval but the public’s as well and would become an object of media interest. Imagine navigating the tender early weeks of a relationship with heavy PR concerns and tipsters dropping a dime on your every interaction. I once had dinner with a man I found super-attractive. Then I learned his wife had taken her own life and decided it wasn’t a good idea. He had two young kids, and I couldn’t bear the thought of their tragedy becoming tabloid fodder.
I did the best I could and kept at it. There was a handsome man who caught my eye at a neighborhood diner. I sent over a cup of hot chocolate （cute, huh?）。 He was a big Wall Street type and I really liked him. We had fun dinners in the neighborhood; he even surprised me with a diamond pendant. But after a couple of months, he ghosted me. Poof. I’ll never know what happened, although I do know New York City is full of crazy-eligible guys whose hearts, for one reason or another, aren’t open for business.
ONE MORNING AFTER the show I picked up the phone. Rabbi to the stars Shmuley Boteach, Michael Jackson’s spiritual adviser, was on the line. “Katie, are you seeing anyone?” he asked.
“Rabbi Shmuley, what’s wrong with you?” I laughed. “You’re married and have, what, like 10 kids?”
“Not for me, silly,” he said. “For Michael. He’d love to take you to dinner.”
What?
I’d met Jackson a few days earlier at his suite at the Four Seasons; he had taken the entire floor, plus the ones above and below for his entourage. There were stone-faced, wired-up security guys everywhere—stationed in the halls, at the elevators; a pair of them escorted me and my producer Yael Federbush to Michael’s suite.
Everything about Jackson seemed soft and weak—his smile, his voice, but especially his hand, which felt like a dead fish when he offered it. He had medical tape running down and across what was left of his nose. There was a computer on the desk behind him with a screen-saver montage of beautiful children.
I’d gone in hopes of snagging an interview and possibly a performance for the show. But talking to Jackson was like talking to a wilting flower—I found it a little hard to get traction. I’d heard he was thinking about playing Edgar Allan Poe in a movie, so I told him Poe had attended my alma mater. Crickets.
After 15 minutes, Yael and I made our way to the door. As we said our goodbyes, I mentioned to Michael, “I’d love to interview you sometime.” He smiled. More crickets.
That he was using Rabbi Shmuley as his matchmaker didn’t add up. Maybe he thought being seen with wholesome me would be good for his increasingly sketchy image, although I had serious doubts it would be good for mine. My answer was easy as ABC: No thanks.