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Is There Still Sex in the City?

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The young woman gave her a look of disgust. “We’re engaged,” she said.

When she walked away, Harold reassured Kitty that it was okay. Although his fiancée looked like a teenager she was actually almost forty. And then he gave Kitty a beaming smile and informed her that he was about to become a father again.

And this is the problem with the hot-drop. No matter how age appropriate he is and no matter how great you are, in less time than it takes to get a blow-dry he has not just a new relationship but a whole new family.

The He’s as Old as Your Father Guy

The reality of the hot-drop odds can cause some women to try to game the odds in their favor by “playing” the game, i.e., dating a man who is fifteen, twenty, even twenty-five years older. Which means, given the fact that you are now middle-aged yourself, a man who is seventy? Seventy-five? Eighty?

You wouldn’t think there would be a large contingent of men around that age who are “dating.” But when you think about demographics and how so many of the boomers are now in their later years, it makes sense that there’s a crop of sixty-, seventy-, and even eightysomething men out there acting like they are thirty-five.

I encountered one of these men at a party given by a married couple in their early sixties. There were lots of fifty­something single women and two or three of these senior-age players, or SAPs. These are older single men of means, meaning they have enough money to add it to their list of attributes and are often still employed in a lesser version of the high-powered career they once had. At some point during the party I must have talked to one of these men, because a few days later, Ron, the host of the party, contacted me to let me know that a fellow named Arnold was interested in taking me out.

Ron was very excited about this. And impressed. He said Arnold was a big deal and he really admired the guy. He’d played Ivy League football and he was once an oilman and a newspaper magnate and all the Park Avenue hostesses were always inviting him to their parties. He was sought after.

I thought I remembered the guy: a tall, thick battle-ax type who was definitely older—too old for me I’d decided.

“How old is he?” I asked.

“He’s a little bit older than I am,” Ron said. “Sixty-eight?”

These guys often lie about their ages. They fudge, somehow forgetting about that truth-telling device called the internet. Sure enough, when I googled him, Arnold turned out to be seventy-five.

That made him much closer to my father’s age than mine. My father was eighty-three; Arnold was just eight years younger. They couldn’t have been more different though. My father is very conservative. Arnold apparently is not. According to Ron, Arnold used to be somewhat of a notorious wild man who went to Studio 54. Even to this day, Arnold still has much younger girlfriends, the last one being forty-five.

“I don’t know how he does it,” Ron said.

I wanted to tell Ron that I didn’t want to be the one to find out.

And so I tried to say no. Peer pressure, however, is one of the things I hadn’t counted on in middle age. And when it came to dating, it turns out there was a lot of it.

My friends kept reminding me that it was good to go out and it was really good that someone had actually asked me out. When was the last time that had happened? Of course I should g

o. What was the harm in it? And besides, you never know.

Of course, the problem with “you never know” is that so often you actually do know.

I knew—or I was convinced I knew—that I was not going to date a seventy-five-year-old man no matter how wonderful he was. What if he fell down? I didn’t spend my life working this hard to end up taking care of a strange old person.

But every time I tried to explain this, I realized how ageist and judgy and anti–love hopeful I sounded.

Because I didn’t know, did I? I didn’t know what was going to happen. What if I fell in love with him? In which case, his age wouldn’t matter, right? Plus, I didn’t want to be that woman—you know, that shallow creature who cares more about practicality than the blind illusions of love.

Plus, as Ron reminded me, I must feel so honored that a man “as powerful as Arnold” wanted to spend time with me.

In preparation for the date, I went to Sassy’s house and we looked at photographs of Arnold on the internet. His photos went back about thirty years. He’d been a big man and rather handsome.

“Oh honey,” Sassy said. “He could turn out to be absolutely wonderful. You must keep an open mind.”

And so arrangements for a date were negotiated. We could have gone to a restaurant in my town, but Arnold really wanted me to see his house, which was in another town about fifteen minutes away. He could pick me up and take me to his town and then I could always spend the night at his house if I needed to and he could drive me back to my house in the morning.

A sleepover? With a seventy-five-year-old man I didn’t know?

I don’t think so.

I was finally able to negotiate that I would drive my car to his house and we would walk to the restaurant and then back to his house. And then I would drive home.

Or spend the night he suggested again, in a friendly manner.



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