Upshot: Even though he thought my Chanel skirt was Gucci, date one had been a raging success. Well, except for one thing—apparently our very fine Barolo cost nearly $500. I hadn’t seen the bill; John paid for dinner. I was mortified and to this day feel bad about it. I must have apologized 500 times. But as first-date stories go, we’ve gotten a lot of mileage out of that one.
A few years later, when John and I jointly formed an LLC, we named it—what else?—A Very Fine Barolo.
79
Are You Ready for This Day?
ALMOST IMMEDIATELY, JOHN broke up with his girlfriend. I couldn’t believe he was bucking the trend, leaving a beautiful 27-year-old for a 54-year-old.
Our second date involved day-drinking. We went to Barbuto and shared a bottle of rosé on a Sunday afternoon （a day John and I now refer to as Rosé Sunday）， then weaved our way to the West Village apartment where his older brother Tom and his longtime partner, Andy, lived. I tried to engage Tom in a conversation about Henry Kissinger’s mistakes in Cambodia but had no real idea what the hell I was talking about; I marshaled whatever details I could from something I’d read in the New York Times that morning. Tom is uber-intellectual （and was roommates with Henry’s son at Yale） and I am no match for him sober, much less with half a bottle of wine coursing through my bloodstream.
We said our goodbyes. In the lobby, John grabbed me and kissed me by the mailboxes lining the wall. I’m not sure if it was the wine or all that talk of Dr. K., but I was definitely in lust. Things between us progressed pretty quickly—so quickly that by date four, it was time for him to meet Ellie and Carrie （great idea for another Meet the Parents sequel—Meet the Daughters）。 One evening, John came to our place a little early to pick me up for a date. Ellie was there with two friends from college. She said, “My mom’s running late; can I get you some tea?”
John said he was fine and took a seat on the maize-colored sofa. Ellie took a seat on the identical one facing it.
“So what are you guys doing tonight?” she said, taking on the parental role. Thank goodness she didn’t ask him what his intentions were.
Next came dinner with John’s kids—Henry and Allie, then 17 and 14—at Red Hat in Westchester, not far from where they lived. I remember them both being sweet but a little quiet, having kinda, sorta heard of me and yet not really sure what was going on. Shortly after we were seated, a platter of fried calamari appeared, followed by a caprese salad for six. My friends always laughed about the freebies that came my way when we were at restaurants, like a massive wedge of cake or extra sides. （“It’s good to be an FOK”—friend of Katie—my pal Mandy would say.） But Henry and Allie seemed a bit overwhelmed. Luckily, they were hungry.
John had already passed a number of tests, but there was a big one up ahead: Could I peacefully coexist with him in my home-away-from-home, East Hampton? As much as I liked him, if you’re with the wrong person, a weekend can be a very long time. So I invited my friends Kit and Laurie to chaperone.
We played Scrabble outside in our bathing suits; when John made a seven-letter word, scoring 50 bonus points, he raised his fists in victory and did a cannonball into the pool. It was funny. And obnoxious. And exactly like something I would have done.
More than anything, I was drawn to his sense of humor. When we were driving back to the city in separate cars, John followed me out of town in his sporty little Mercedes convertible. When we got on I-495, he pulled up next to me—with an open book propped up on the steering wheel, as if he were casually reading while driving. （Don’t worry, he wasn’t.） He just looked over, smiled, and waved before passing me, delivering an excellent sight gag.
A BLOSSOMING ROMANCE WAS a great diversion from the pressure of launching a hotly anticipated talk show. Apparently, Jeff and I were a huge get for ABC—the executives felt sure they had a winner on their hands.
But they didn’t want to leave anything to chance. The network was conducting extensive research to figure out who our target viewer was. They came up with a detailed psychographic and even gave her a name: Lisa, from Elmhurst, Illinois, home of the former Keebler factory. Lisa is 45 years old. She has three kids and works part-time. Her household income is $44,000 a year, and her house is worth $179,000. According to the psychographic, Lisa struggles with “overs”—she’s overworked, overweight, and overwhelmed. But she is “resilient” and “optimistic”; for Lisa, life is good, but life is hard.