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Truth or dare

The Black Swan event I was waiting for occurred on a sunny Tuesday afternoon; I matched with Babelicious. She was one of the prettiest women I'd ever seen; blonde hair, blue eyes and perfect bone structure. In addition to being a striking beauty, she had a successful career as an entrepreneur in fashion, and her text exchanges displayed wit and charm. In sum, the whole package.

Instead of meeting for a glass of wine at one of my typical spots, I booked a table at an upscale Lebanese restaurant called Ilili. She arrived 5 minutes late and apologized profusely. From her accent it was obvious she was Australian which explained the lack of New York edge and attitude.

Babelicious was the most charming date I had. She carried on delightful conversation, was poised, funny and even humble. At one point she said "I don't date much. How am I doing?" I almost choked on my Cuvaison Pinot Noir. If there were an app to deliver an engagement ring to the table, I would have ordered one, slipped it on her finger and pledged my everlasting love to her before dessert.

I reached out the next day to tell her how much fun I had and then followed up by inviting her to a cocktail reception. But I never heard back. Oh well. It was kind of a relief to know she wasn't so perfect after all.


Shortly after Babelicious ghosted, a friend called me and said "I gave your number to a colleague who wants to set you up with someone. I really think you should go out with her." A date that didn't come through swiping was very refreshing; almost too good to be true — until I found out that she was a successful Wall Streeter.

One of the rules I tried to follow was: don't date Wall Street women. They usually had entitlement issues and from past experiences, just weren't that much fun.

Of course no one who has a banking career refers to their livelihood as "working on Wall Street." They changed the name of their profession to "Financial Services" after they blew up the economy in 2008. It sounds so pleasant to the ear — Financial Services. It gives the impression that when you walk into a bank, someone will be there to greet you with a smile and hand you a cup of tea. In reality, their job is selling obtuse financial products to unsophisticated customers and sticking their blood funnel into anything that smells like money, as the great Matt Taibbi described it.

In spite of that, I agreed to meet Ms. IPO. But I made a personal decision to do everything I could to get her not to like me. In the best interest of everyone involved.

Before I could plan something for us to do, she proactively made me an offer I couldn't refuse: 10th row center seats to a Rangers game at Madison Square Garden. Done! I dressed down, made a point of drinking more than normal and didn't hesitate to drop a few F-bombs. By the third period she was showing me iPhone photos of her dinner with Kate Middleton at Buckingham Palace. The strategy was failing; she liked me.

Confirmation came the next morning from our mutual friend. "Heard you guys had a great time last night. She can't wait to go out again."

I had to take things to the next level, get her out of her element into the filthy side of New York. I was sure that would turn her off and end things once and for all. So for our next date I suggested a performance art venue in the East Village. It was a circus/trapeze show in an abandoned bank, with compelling visuals, pulsating music, and strong sexual themes. During the final scene of the event, the audience was encouraged to dance along with the half naked performers in the middle of the room. Before I knew it, we were making out on the dancefloor and grinding.

"How about a nightcap and a game of truth or dare" she asked me.

"Game on!" I responded, admittedly shocked and maybe a bit intimidated. I marched her over the the W Hotel at Union Square and we found a cozy corner.

"What was the most unusual place you had sex?"

"Would you rather tie someone up or be tied up?"

"Describe your most intimate sexual fantasy!"

No question was off limits. Every intimate detail about our past was open for questioning. By removing all inhibition, we really started to bond. And then I started to like her. Maybe all of my sweeping generalizations about Wall Streeters were wrong. I wanted to send holiday baskets to the Goldman Sachs board of directors. My values were slipping away. I was losing my mind.

We picked up The Vessel and motored uptown. I was only expecting a good night kiss, but instead she invited me upstairs.


Her apartment was epic. Four thousand square feet with views of the city in every direction, every inch of it designed, curated and polished. After the tour we retired to the family room. I took a remote control and pushed buttons until I found the shagadesiac setting for lighting and music. There were electronic controls for everything — everything except taking off her top, which I managed to do manually.

I woke up in her bed in the middle of the night needing the loo. Since the master bath was being renovated, I had to venture out into the dark apartment in search of another, which I eventually found, but getting back was no easy feat. Groggy and half asleep, I stumbled into the laundry room, the fitness room, a guest bedroom and then somehow made a second loop into the kitchen. While I was there I indulged in one of her mom's super yummy cookies. I had to make a mental note to myself: leave a Boy Scout trail if you need to pee again.

The romance progressed slowly. One of the things I thought about was whether we should be sharing the cost of our dates. Up to this point in time, she hadn't offered to pay for anything. I always found that the women who could least afford to split the cost of dates offered to pay the most. I was usually terrible about addressing it too. This was highlighted one afternoon when she suggested a trip to the Guggenheim to preview an artist whose work her art curator recommended for the hallway. A stare at the ticket counter implied that the $50 entry fee was my responsibility, and reluctantly, I paid it. It was a 30 minute stay at most for rubbish art and a museum whose staff I always found to be rude and pretentious.

After a few more encounters the inevitable text arrived; she was no longer interested in dating. I can assert that men and women have totally different ways of ending a romance. Men apologize and blame themselves as is evidenced by the cliche "it's not you it's me." Women are ruthless about it; they carpet bomb the entire relationship until it looks like the Syrian city of Aleppo. There is nothing like a scorched Earth policy to show you're not weak.

Other than the style of the breakup communiqué, I can't say that I blamed her. I didn't put very much effort into the relationship and felt from the beginning that our sense of humor didn't click, which to me is a critical part of bonding with someone. So in the end, I ironically got what I wanted in the beginning, only it didn't feel quite as good as I expected. Maybe because I realized that I'd never have another one of her mom's cookies.

In good health, wine, and tequila,


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