Online dating | Money | Women


Can you write youself into this soap opera?

It's always refreshing when you match with a woman in NY who doesn't work in financial services, particularly when she has an interesting career that you know nothing about, like writing for the most popular soap opera on TV for example. I imagined that someone who spent the last 20 years of her life dreaming up scandals and acts of depravity for morally challenged characters would be just what the doctor ordered.

We got off to a unusual start when after asking her out, she insisted on a pre-date. Just what the hell was a pre-date anyway? As if dating weren't hard enough, was it really necessary to dissect it into more intricate parts? My Google research pointed to a short, 10 minute face-to-face meeting with easy escape routes in case one needed to pull off an Irish exit. Or mix into a crowd and jump on a bus incognito, like a villain in a James Bond movie. Since the concept of a pre-date was so ridiculous to me, I tried to come up with an equally absurd activity, so I suggested riding the escalators in the mall at Columbus Circle, which she surprisingly accepted. Our pre-date wound up lasting 2 hours and even included a cappuccino! However, when I tried to get close to her she seemed uncomfortable. Still, I was open to seeing her again.

Our next meeting was at a proper restaurant, which happened to be Crave Fishbar. Her stories were fantastic. I got the inside scoop on behind the scenes writer shenanigans that spanned HBO, Showtime and Comedy Central. She was marvelously entertaining. I learned that there were soap fans who not only knew the characters intimately, but also ferreted out who the writers were, and found ways to contact them and beg for storylines.

I looked into her eyes and made romantic overtures toward her, but each time she recoiled. At the end of the evening I tried to kiss her goodnight but she turned her head. She had confessed to not having any recent relationships, and although I think she was interested in me, I envisioned a multi-month courtship that ended in not-so-good sex. Like Sybil Vane in the Picture of Dorian Gray, it was only in the world of daytime TV drama where she actually lived. Outside of art, she didn't exist. If only she could write herself into the soap opera of her own life!


It reminded me of an ex-ballerina I went out with. Ms. Prima Ballerina's profile indicated she was a fun party girl. Great! On our second date to a ballet at Lincoln Center, I tried to hold her hand and she jumped back in horror, as if I had pulled out a pair of handcuffs and insisted on bolting her to the toilet in the handicapped bathroom.

What both of these women had in common — in addition to asexual behavior — was that their profiles emphasized their desire for an LTR, dating parlance for long term relationship. However, no one told them that you will never have a long term relationship if you don't have a short term relationship and the prerequisite for that includes holding hands and kissing on a second date. An LTR for these types of women just wasn't going to happen. Ever.

It seemed to me that they viewed dating like the old children's board game Chutes and Ladders. You move your piece onto the square with the ladder and immediately level up into a monogamous, long term relationship with a handsome, successful, funny guy who has an apartment off the high line. No need to bother with the interim steps.

I did put a rule in my playbook after the ballerina incident stating that if I didn't get a passionate kiss after a first date it was instant game over! (Assuming mutual interest and a reasonable amount of time spent together). Since both of those women ate huge meals which they never offered to share the cost of, I felt no guilt in cutting them loose for lack of affection.


It would be irresponsible and downright negligent at this point not to mention the role of money in NYC dating. It doesn't take more than a few experiences to realize that there are a significant number of women who only go out for a free meal, and a hell of a lot more who feel entitled to way more than that.

Even if you are a personality profiler trained by the FBI, you are still going to get burned. It's like thinking you can go Bass fishing in the Amazon and avoid mosquito bites. They're gonna get you.

This usually takes the form of women thinking "even though he's totally not my type, he doesn't seem like a psycho so I'll let him buy me dinner." Not my type in this case means, he fell below the unreasonable expectations that were set, not only the woman, but also by her girlfriends; he didn't earn enough money, wasn't tall enough, didn't live in the right neighborhood, had a kid, wasn't athletic enough, wasn't alpha male enough, etc. It's hard to know you're going to be played until it's too late.

One workaround to this is meeting for drinks only. However, in New York, where everyone works until 6:30 or 7:00, a drink inevitably turns into dinner so it's far from foolproof.

Some women have mastered this skill to the level where they get a guy to finance multiple "all expenses paid" dates without any intention of intimacy or relationship. I got royally played by the Director of Sales of a famous women's magazine. She was truly world class. Not only was she pretty but she could turn on the charm and amp up the touchy feely flirty talk so high that you felt honored to hand over your credit card.

I even employed the "let's meet for a drink" strategy for our first date, picking a simple restaurant and thinking I had the upper hand. Then she pulled a last minute location change, telling me to meet her at ABC Kitchen. She arrived 15 minutes late, ordered a counter full of food, the most expensive white Burgundy available, and suddenly ran off an hour later to a "work dinner," leaving me with a $175 bill. Checkmate! Beautifully executed!

I wasn’t planning on seeing her again, but after receiving a few very flirty and suggestive texts, I somehow found myself enthousiastically inviting her to an overpriced dinner at Salinas on 9th Avenue. She started speaking of us as a couple and I assumed the next date would be the closer.

For her next act on date number three, she made it seem like she was going to treat me to dinner saying "there's a great Italian restaurant in the West Village I want to take you to." I immediately agreed and off we went to I Sodi where we feasted on veal chops, home made pasta and Nebbiolo. When the bill came she gracefully slid it over to my side of the table and gave me the same sultry look you get from a pole dancer who wants you to stuff a fiver into her g-string. Out came my Amex card. Just when I thought I was going to be invited upstairs to her place, the porn star persona quickly morphed into a dental hygenist and the date came to an abrupt end.

I should have learned my lesson right then and there. Mais non! It permanently unravelled at the community backyard table at Bhustan restaurant on a warm summer eve where textbook narcissist qualities emerged, the signs of which were there from the beginning. It was topped off by her saying "Ask more questions about me! I'm really a fascinating person."

When she stepped out to take a phone call, the guy next to me — who was there with his girlfriend — leaned over and said "dude, it's none of my business, but after I got divorced I made sure to avoid women like that." I not only thanked him, but bro-hugged him.

There's a John Maynard Keynes saying about the stock market that goes something like this "the market can remain irrational longer than you can remain solvent." I was finding that dating wasn't entirely different.


A few days later, I was at the bar at Cookshop with a leggy, attractive German woman who I knew through the art world. We were just friends although sometimes we held hands and on one occasion shared a smooch. A few glasses of Pied a Terre Cabernet had been consumed when she quite suddenly put one hand behind my head and pulled my mouth into hers, giving me a hair raising passionate kiss. With her other hand, she not only grabbed my crotch but squeezed it hard enough to let me know that she meant business. "Honey, we go across the street and get a room at the hotel?" she asked.

Now there was a woman who could write herself into her own soap opera!

In good health, wine, and tequila,


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