Two women – as opposite to one another as humanly possible – gathered on a rooftop with their significant others and a small group of friends for a birthday party on a warm, clear Sunday night in New York City. The first, a dark-haired artsy rebel type covered in ink, said hello and then proceeded to ignore my presence completely while nervously watching her sort-of boyfriend suspiciously glare at me in the distance. The other, a busty, bubbly and blond All-American girl, nearly bit off her tongue trying to explain what she and her man were doing there, since they usually reside across the country.

Having spent nights in bed with both of them, it was an uncomfortable scenario to encounter.  Yet I couldn’t feign surprise.  Somehow, in less than two years of living in New York, I’d managed to hook up with a good portion of my friend (we’ll call her Betsy) Betsy’s social circle. Betsy works in fashion and surrounds herself with cute women. And I’ve been told that I happen to be one of the only straight and ‘normal’ guys that these women encounter in a city full of snobs, slobs and men not interested in the opposite sex.

Circumstantially, I wasn’t set up to date either of the women on the roof when our attractions became physical. In one case, there was the issue of her being in a sort-of relationship (the artsy girl).  And in the other, the issue of 2,000 miles (the All-American). These were safe scenarios for knowing that I would have a night’s companion without risking a life’s commitment.

Being single in New York has become a constant analysis of that same risk and reward. Let me be clear – I am not the type of person to endorse cheating, simultaneous sexual partners or sex without emotion. I have had a single one night stand that involved a complete stranger in my life, and it occurred on vacation. Sure, I’ve had plenty of single nights spent in bed, nearly rounding third.  But I’m not into counting homeruns or the other macho shit that guys do. I don’t walk around comparing one lay to the last or keeping tally, either.

To be completely honest, I am a hopeless romantic caught up in the mess that is the Manhattan dating scene.  Luckily, I’ve learned a few things along the way.

Born and raised in the Midwest to parents who have been happily (most of the time) married for 30 years, I developed a picturesque view of the concept of ‘soul mates’ around the age of five.  While working in a movie theater for four years throughout high school, the cinematic representations of love that I was constantly seeing on-screen only made this fairytale idea of devotion even stronger. My search for the relationship that mirrored my parents became my purpose.

I thought that I’d found it in my first long-term commitment, which lasted 3.5 years. That was followed by another 1+ year relationship – one that I worked too hard for, and let go of in defeat. It was only then that I finally came to see that my real purpose was beyond just having someone to share my life with.

So at the age of 24, I found myself in a place that I hadn’t been in my adult life: single. With little tying me down to the Midwest, I caught the next plane out and moved to New York to pursue career goals in marketing and experiment with both writing and life. For the first time, I had the perspective that I needed no one, wanted nothing from anyone, and simply hoped to connect with the world through myself.

This masturbatory new reality had me jumping from one woman to the next; having a few weeks of fun with a friend-of-a-friend before moving on to a Brazilian girl who I met at a concert, and then onto a short stint with an attention-fueled FIT student who still needed a fake ID.

Two years later, things aren’t much different. I have yet to have a lasting relationship in New York, and I continue to have no trouble finding a date or connecting with a stranger. In the last two months, I’ve had a 3-week whirlwind fling with a Dutch exchange student who has since returned to Europe, walked the thin line of appropriateness with work colleagues, watched as an Indonesian girl sleepwalked through my room while wrapped in my bedding like a mummy, and been picked up by a Colombian bartender who claimed that she hated games but decided to play cat & mouse for the weeks that followed. All of that somehow took place despite the fact that I’ve been traveling out of the state for over half of that time span.

What I have come to realize is pretty simple: 1) I love women. 2) I am more attracted to women based on personality, chemistry and curiosity than on looks. 3) By never trying to be anything more than myself, I have a far greater chance of connecting with women – both in and out of my league – in New York.

With that, I feel it is important to share my newfound perspective on dating with readers.

More guys need to slow down and realize that New York isn’t their playground for picking up chicks and trying to get laid. Women here are sophisticated and self-sufficient. Most of them are highly educated and have established strong networks of support in their lives.  They see the right man as a complement to their lifestyle, not a necessity. These women have options beyond you, and you need to recognize that.

Women want to be spoken to in a way that demonstrates respect and treats them as equals. They do not need you to fall hopelessly in love with them on Date Two or cater to their every desire. Women want security, laughter and space. They don’t want to be neglected, and they don’t want to be smothered. They want to feel sexy and know they are appreciated.

Women like a guy who isn’t afraid to be vulnerable, because it is a part of confidence to accept weakness. Figuring out how to please them in bed is certainly helpful.  And keeping a part of yourself open to mystery also seems to have some appeal.

I moved to New York for me, and I remain single because I am not ready to give a girl the time and attention that she deserves – enough so that I can look at myself in the mirror and say that I’m a good boyfriend. The thing to remember is that a large percentage of women are living the same way. They don’t have time for a relationship, are likely not looking for one, and need you to get over yourself if you think that you’re going to be the guy who convinces them otherwise.

The dating scene for twenty-to-thirty-something New Yorkers is full of members of each sex who are craving true connections, not just physical ones. But intimate moments that help you mature emotionally do not need to be cultivated in relationships. If you treat every woman as a possible soul mate, you start to realize that you’re learning from each encounter and getting closer to the point where the best person for you will reveal herself.

Despite the common misperception that I run around with a lot of girls and am afraid of (or incapable of) commitment, I really am working towards a long-term bond with someone. It is in the process of finding aspects of beauty in every woman that I start to strip away the ugliness in myself and get closer to what I am looking for. Sometimes I slip up and act like a jerk, but that happens less frequently.

Taking expectations and necessity off the table was the most important thing that I have ever done in my dating life. It brought me to a place where I can stand on a rooftop with two women who I’d previously connected with, be happy that I know more about who I want to be with, and feel entirely okay that I’m not with either one of them. They seem to be doing just fine without me too.

About the Author: Jeff is a freelance marketing consultant by day and writer by whatever his little free time allows. He is not big on traditional dates, enjoys a good book and spends more time in airplanes than cars. Jeff appreciates the history of brewing and cinema and believes that most of life can be explained in alcohol or film, and the rest between the notes of a rock song. He is currently working on a TV treatment for a series that draws from the randomness that has been his life, but commercially sensationalizes it to be marketable because that is what he learned to do in school. He appreciates real art and can often be found escorting cute women around MOMA. Email him at jmtnyc@gmail.com or stalk him with a Google search and see what you find.

Aug 5, 2010

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