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Wharton on the West Side

I started to feel like I was going on the same date over and over again, particularly when I was navigating the never-been-married, no-kids demographic. It was Groundhog Day.

Travel was the benchmark of personal status to these women. And we're not talking about a weekender to Paris for a grass fed steak at Anahi either. To get credit in their eyes the travel had to be exotic, the more outrageous the trip the higher the social status achieved. I heard about excursions to yoga retreats in Bhutan temples, glacier climbing in New Zealand, and meditation getaways in remote Gambian Kasbahs. And quantity mattered too. The common refrain was my passport is at 50 countries and counting! For some reason, 50 was the magic number. Never less.

Inevitably, the inquisition would come my way. "Where have you been lately?"

Well, truth be told, I've been back and forth to LA a lot lately, although years ago I travelled all over Europe and South America. But not to the exclusive resorts and unusual locales that would have given me unfettered entry into the club.

I eventually came up with the following response: "I'm going to parachute into a live volcano in Halmahera next month. Should be fun." This always got a nod of approval because they had no idea where Halmahera was — and were too proud to ask — and figured the trip had to cost a solid 15 grand. Some ACTUALLY asked if they could come with. I used to imagine my date and I in a helicopter above a live volcano spewing lava: "OK, you jump first, I'll be right behind you with a picnic lunch from Eataly."

One woman I met for dinner created a full fledged marketing business focused on this exact demographic; a community for childless women who had lots of money to spend on nieces and nephews. She became the expert in this space, with frequent TV appearances and celebrity endorsements. The question I had for her was why didn't these women ever marry? Without missing a beat she answered "because they weren't willing to settle."

Now I can understand if a woman is a doctor in Sub-Saharan Africa. There may be a legitimate shortage of single, educated men. But Manhattan doesn't exactly have that problem, does it? It couldn't have anything to do with unreasonable expectations, could it? This exact narrative — that so many NYC women are single because they weren't willing to settle — repeated over and over until it became fact, contributed greatly to my inspiration for writing these episodes.

While I clearly didn't buy into the "not willing to settle" pretext, there was clearly something broken in the never-been-married, no-kids demographic in New York. They were professional daters who were desperate for love, yet incapable of a romance of any duration. And not just the women. The men were pretty bad too. For proof, you just needed to go to a party in the Hampton's; lots of alcohol and banter, but like panda bears in captivity, they just couldn't mate.

Maybe it was the endless search for the perfect partner; the unrealistic expectation that such a person even existed that created the glut of perma-singles in this demographic. Anyone with a failed marriage or two under their belt knows that there is no such thing as a perfect mate. Successful relationships require 1) compromise, 2) the ability to let a lot of shit go, and 3) a strong cocktail when numbers 1 and 2 don't work.


Around that time I stumbled on a Huffington Post article entitled Men May Like The Idea Of A Smart Woman, But They Don't Want To Date One. It was written by a self described "dating expert" who also happened to be — cue the suspense music — a woman. What was obvious click bait to me was clearly taken as empirical evidence by her faithful readers.

As a sheer coincidence, I matched with 2 Wharton MBAs later that day. I reread the article. If her premise were true, there was an entire demographic of smart, eligible women who couldn't find a partner because men were too intimidated by their intelligence. Not me! I was excited to plunge into this underserved market and I quickly arranged two drink dates.

I arrived to meet Wharton One at 6:30 in South Williamsburg at a place called Rye, and found her sitting on a banquette. She introduced herself and immediately said "I have to leave in an hour to catch a flight to Boston." She told me about her job, her kids and her ex-mother in law. After 45 minutes she was up and out. That sort of efficiency may be rewarded in the corporate world but it doesn't build the foundation for a good romance. I wondered whether the Shuttle even ran that late but decided it wasn't worth any more thought.

Wharton Two arrived at Cafe Tallulah on time and straight from work. In her profile she said that she wasn't your typical Upper West Side Jewish woman, which was refreshing. However, from the start everything seemed very business like. It felt more like a job interview than a date but I tried to make the best of it. I injected humor, brought up some irreverent topics, and said fuck twice, just to get her to loosen up and make the event seem like an after work activity. But it was futile. She talked about getting up at 4:30 every morning to run around the reservoir, her synagogue, and her condo by the park. We managed to break the 45-minute barrier — but just barely — and then she was on her way.

Starving, and more sober than I wanted to be at that hour, I headed to the Mermaid Inn on Amsterdam to sort it all out over a salmon filet and glass of Sancerre. The bar was packed and I squeezed into the only bar stool available. The couple next to me were obviously on their first date.

The guy was dressed super casual, without any sense of style whatsoever. He said he was a soccer coach and looked it. His date was Latina. I think she said that she worked in a restaurant. Her outfit was stunning; a sexy black dress and black lace-up sandals, a sparkly necklace and a spray of perfume.

His conversation wasn't particularly inventive; he talked about sports, schoolyards, his job, etc. And yet, she seemed to hang on every word. She listened, she laughed, and she offered funny anecdotes. She flirted! What an absolutely charming date! As I ate my salmon I tried to find a word to summarize what was so compelling about her, but I couldn't find it. And then, it came to me. PLAYFUL. That was it; she was PLAYFUL! The date was PLAYFUL. It was fun. All in stark contrast to my Wharton dates.

Maybe men do like the idea of a smart woman, but if you're not flirty, fun and playful you wind up as a statistic in a dating expert's blog. Even a real dating expert like Mandy Stadtmiller would agree to that!

In good health, wine, and tequila,


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