Playing to Win in the Game of Love

At the age of thirty, I was starting over in the dating world, and looking for the total package: someone smart, pretty, easy to be around, and definitely someone with whom I would have great chemistry. That’s a tall order, even under the best circumstances. But when you’re running two companies, and have next to no free time? Practically impossible! So I decided it was time to use my aptitude for innovation on a totally new subject: myself.

A Year of Insanity

By the time I hit my early 30’s, I had been living in New York City for my entire life. The years had been full of highs and lows, both personal and in business. There was my father’s passing, when I was only a kid. My mom’s struggle with chronic health conditions and building a business to support us. The typical ups and downs of middle school and high school. Falling in love with nightlife at the very young age of 14, and staying in love with it through high school, college, and beyond. Working like crazy to get into med school, only to realize that it wasn’t for me, and dropping out to join the dot com boom (and bust). And of course, the all-consuming task of building JoonBug into a juggernaut that effectively brought the nightlife industry into the digital age.

I wasn’t only running JoonBug, but I was also nurturing a second company on the side: EZ Texting, which was a high growth tech startup. On the business side, things were booming. But in my personal life, a recent broken engagement had left me feeling jaded and somewhat cynical about long-term relationships.

The truth was, although I was living all of my life at my office, clubs, bars, and restaurants, my personal goals were far from those of a playboy or party animal. I really wanted to meet someone like minded, a girl with traditional values who was ready to get married and start a family. 

But starting over was difficult, in more ways than one. Not only did I have to move on from the long-term relationship that had ended; I had to do it while holding down two more-than-full-time jobs, and with extremely limited free time that was usually just a couple of hours at the end of a very long night. Sure, there were plenty of attractive women to talk to and go out with, but none of them were the type of woman I was looking for.

Still, I went on like that for about a year: dating people I was attracted to, but whom I ultimately didn’t mesh with—and sometimes didn’t even like very much! And not just going out once, but continuing to date them, hoping that something would click. Inevitably, this would lead to calling it quits… only to do it all over again, repeating the same tired formula, hoping that it would somehow turn out different the next time. 

What’s that called? Oh, right. The definition of insanity.

New Inputs, New Outcomes

Finally, I had an epiphany. After a year of not even coming close to meeting the right person, I realized that I was stuck in a rut that would never (or almost certainly never) help me achieve my goal. Because for me, meeting the right woman was a goal. A lot of people don’t like to think of relationships in that way, because it doesn’t seem “romantic.” They feel that finding love should happen serendipitously, naturally, without effort… or else it isn’t real. 

I didn’t see it that way, though. Finding a spouse really was a goal, arguably my most important, life-altering personal goal. And so, after failing at that goal for a year, I had to ask myself, “What am I doing wrong here? What do I need to change?” And the cold reality was this: I had to change myself.

Instead of continuing to live my life in its usual pattern, I had to be willing to do things I wouldn’t normally do, go places I wouldn’t normally go, and essentially get comfortable being uncomfortable. It was time to change the inputs, in order to get a different outcome!

So, I made the choice to deliberately try lots of different things—new inputs, if you will, into my routine of meeting and dating. For instance, I knew that I wanted to meet and marry a Jewish girl, so even though I’m not a religious person, I started going to synagogue on Saturday mornings! It felt really unnatural at first, but it wasn’t a bad experience at all. Ultimately, I didn’t meet my wife that way, but I did meet a bunch of great people, and through them, even more people! My social circle was widening, and the network effect was increasing my odds of eventual success.

With that in mind, I also went all-in to leverage my existing network, by unabashedly telling everyone that I was looking for a wife! That might sound a little bit embarrassing, but it was a valuable strategy. Friends who knew me well had a high chance of introducing me to someone I might be interested in and compatible with. But first, they needed to know I was looking!

Other things I tried included going to the gym, and even yoga—the obvious perk being that hopefully I would meet someone who was fit and cared about their health. It also incentivized me to spend more of my limited free time taking care of my own health, which was definitely beneficial.

Then there were charity events, which I hadn’t really done before, and meetups for things that I enjoyed, like computer science. You never know! I also went to random events that I found online, and purposely hung out with people I wouldn’t have gotten to know before. 

I even made a brief foray into the world of online dating! These days, online dating is very normal, and a lot of people find great relationships through apps. But back then, it was much more taboo. There was a perception (not entirely unfounded) that the only people who were into online dating were people who couldn’t get dates “the normal way.” So the whole ecosystem was small, not great, and carried a certain social stigma. But I was in a whole new frame of mind. Instead of making excuses and avoiding discomfort, I told myself, “I can’t get embarrassed. I have to be willing to try new things.”

It was a huge shift for me to start going places and meeting new people, on my own. I had to learn to be okay with going out solo, and I had to learn to be sociable, talk to people, and make friends quickly. Up until that point, my life had actually been moving in the opposite direction. Most of my friends had already begun to get married and start families, and instead of being ready for a night out, they were living in the suburbs and taking care of their kids! As a result, my social circle had shrunk over time, and I would often find myself torn between going places alone, or hanging out with people I didn’t necessarily want to spend time with, or even worse, hanging out with my friends and their kids. So I would just stay home.

With this new outlook, however, I started thinking of meeting my future wife as, well, my job! I was totally committed to it. I wanted to meet the right woman and fall in love. When it came to that process, my newfound philosophy was that I would only get out of it what I was willing to put into it. And it all helped to prepare me for meeting Diane.

A Date with Fate

One night, a friend of mine, Aly Govani, called me up. We started out as work acquaintances but ended up going out together a lot and having a great time.

That night, he asked me if I wanted to come to an event put on by a friend of his. It was for a charity called Seeds of Peace, which brings together youth from areas of conflict (such as Israel and Palestine) fostering communication and mutual understanding, with the hopes of changing their perspectives and bringing those changes into the future. 

This particular event was at Cipriani Wall Street, a stunning, elaborate venue known for excellent food, cocktails, and service. Aly told me he’d meet me there, and I said “Great!” So I finished work, got dressed up, and jumped in a cab.

Just as I climbed out of the cab and slammed the door behind me, my phone rang. It was Aly. He apologized and said that a work emergency had come up. He wouldn’t be able to show until much later, if at all. 

So I stood there for a minute, wearing my suit and holding the tickets, and thinking. Had it been a year earlier, I would have just headed right back home (or maybe not even have made plans to go to the event in the first place!). But now? “Ah, to hell with it,” I said, and started up the steps. 

Cipriani Wall Street is a very BIG space, holding maybe a thousand people. I took it all in, heading for the bar and keeping an eye out for people I might know. My main agenda at that point was to avoid being that awkward, creepy guy alone at the bar! So it was a relief when, out of the corner of my eye, I saw a girl I kind of knew.

We had met through mutual friends when she was doing an event, and needed an alcohol sponsor. At that time, JoonBug was working with Trump Vodka, and we sent her a few cases. Afterwards, she friend-requested me on Facebook, and for some reason, every time I logged on, pictures of her dominated my feed—often hanging out with people I knew, and going to places I also went to.

However, I hadn’t run into her in person until that point, and aside from an email or two, we had never spoken. But I gathered up my courage to go and say hi anyway. It had gotten a lot easier to do things like that over the previous year. Although a pretty blonde-haired and blue-eyed Russian girl, she wasn’t my type. I usually went for the opposite kind of look, but at that point I wasn’t looking for a date, just someone to talk to so I wouldn’t be alone at this event! 

So I approached her and introduced myself, asking if she remembered me. She did, and we began to chat a bit. That was when I saw another girl walking toward us. She was gorgeous: long, wavy black hair, striking features, and a supermodel figure showcased in a strapless, black-and-white cocktail dress. Her dark expressive eyes were especially compelling: even from a distance, they were burning a hole in me! They also made it clear she wasn’t headed our way for a friendly chat. 

When she reached us, she didn’t even glance in my direction. Instead, she said directly to Anna, in a snappy tone, “Come on! Let’s get out of here.” With that, she turned on her heel and started to walk away. 

Not the words I had hoped to hear. I wasn’t sure how to respond, and said helplessly, “Whoa, whoa, whoa, what’s going on?”

Anna also protested, explaining that everything was fine, and that she and I knew each other from work. She introduced her friend as Diane, and Diane reluctantly said hello.

So we stood in an uneasy triangle, with Diane clearly still wanting to leave, me wanting them to stay, and Ana somewhere in the middle! I tried to keep the conversation afloat as smoothly as possible. It wasn’t easy, but it worked. Slowly, Diane’s demeanor changed from angry to relaxed, and her arresting eyes became warm and friendly. She laughed and smiled, with a flash of dimples and perfect, even teeth.

Later, I found out that the hostility had to do with the fact that Diane thought I was hitting on Anna, who was dating Diane’s best friend Esmond. Once that idea was laid to rest, we all started getting along really well. Eventually, a group of my friends showed up, along with Aly, and we all had a great time. After a few hours at the Seeds of Peace gala, we decided to go to Green House, a nearby nightclub, and hung out until three in the morning. Diane was easy to be with and she actually laughed at my jokes. Throughout the night, I had a chance to find out that we had gone to the same college, although I was eight years older, and that she was currently a student at NYU Dental. We discovered that we had some mutual friends too and that our parents immigrated to America the same exact year! Although from different countries, it sounded like we had similar upbringings. I was quickly falling hard for Diane and by the end of the night, I had gotten her number—and even held her hand.

After that night we started hanging out and texting a lot. I even remember at one party the coat check girl asked for Diane’s name, and I jokingly said, “Mrs. Neman,” to which Diane laughed, and wittily snapped right back, “uh, in your dreams!”…

But I guess I called it!

New Horizons

Looking back, I don’t think I would have met Diane in any other situation. Although I put a lot of hard work into changing myself, there was of course a certain serendipity to it, after all. For instance, I later found out that that was the first night Diane had not gone out to a party in months because she had just finished studying for exams. But I do believe the hard work I put in opened up the door for good things to happen. Sure, there were dead ends along the way. The progression wasn’t a straight line. But I don’t think I would have been ready to meet Diane if I hadn’t persisted in changing myself and trying new things. If I hadn’t been committed to that process, I probably would have gone home when Aly canceled—and then I would never have met Diane! Or you never know, maybe my newfound ability to seek out different environments would have led me back to the NYU library to find her!

As time went by, the love was real. Case in point: by the third month that we had been dating, Diane told me that she needed to perform a couple of required dental procedures for her program at NYU. In dental school, sometimes you have to find your own patients, and they have to be willing to come in and pay to have a student do the work! It’s a crazy process. 

I’m sure you see where I’m going with this. It’s got to be true love when you’re willing to let your girlfriend jab a needle in your mouth and remove perfectly good fillings! And I think it definitely proved to Diane that my feelings were genuine!

So that’s the story of how Diane and I met. Now, we are happily married with two amazing children. And when people tell me they’re searching for “the one,” the advice I give is this: be willing to face your situation honestly, to change it, and to keep on changing it, always trying new things and new approaches, until you find what you’re looking for.

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