Romantically Illiterate on the UWS

Out in Los Angeles, or what I like to call the “real world,” attraction is an easy concept to qualify: he asked for my number, he tried to kiss me, I gave him my number, we flirted, he told me he thought I was pretty. On the Upper West Side, all those very basic signs that let me know I am desirable in the secular world go out the window. On the UWS, I am romantically illiterate.

I can stand in a room of hundreds of young Jewish singles (ages 25-35, approximately) and truly believe that no one is interested in knowing me, romantically or otherwise. In my many brief UWS experiences, people never approach strangers, choosing instead to meander from acquaintance to acquaintance, exchanging niceties, and complaining to close friends that they wish the new faces in the room approached them or that the new faces would be amenable to being approached. No wonder insecurity spreads like a pandemic through the avenues of the Upper West Side! Each trip I take to “the scene,” I find myself second-guessing my social skills. Forget about whether or not I am attractive, am I socially adept? I barely succeed to add five new names to my list of “approachable acquaintances!”

The good news is, out in the “real world,” I know I am both attractive and socially proficient, and because of the confidence that goes along with recognizing both of these truths, I keep sending myself back to “the scene” in the hopes that I will meet someone worthwhile in spite my UWS illiteracy and the stunted and peculiar social norms of the UWS.

On this most recent trip, I did succeed in uncovering a few interesting insights into the UWS mentality that might help me in the future…

It is self evident that the eligible men on the UWS are afraid of approaching women. Why? Well, due to the overwhelming number of eligible women and the, unfortunately, poor offering of eligible men on the UWS, the men are pegged on a hierarchy based on a number of dateable factors (such as looks, financial means, intelligence, socially aptitude/cool, and overall desirability). All the eligible women believe that they deserve a man at the top of this hierarchy. And, if the eligible women are approached by a gentlemen of whom they have no knowledge or previous encounters, they are afraid that this stranger is nothing better than an awkward third, forth, or fifth to the finest (or most player-esque) single men on the UWS. They want “better.”

Instead of accepting the approach as complimentary, and figuring out the desirability of the new face over a drink or a conversation in shul, the eligible female thwarts the courageous come-on with palpable disinterest, or an urgent need to meet up with a friend across the room. Consequently, the non-“players” on the Upper West Side have learned not to approach women. And women are left lonely and wondering how to get a date.

So how do people meet, how are matches made? Very reminiscent of the good ol’ shtettle days, the UWS has reinvented the matchmaker. The modern matchmaker is a peer who is somehow connected to both an interested individual and the object of his/her interest. In other words, if a girl sees a guy and finds him attractive, she finds a friend or a friend of a friend to set the two of them up on a blind date. And so the matchmaker is reborn.

The problem with this new matchmaker system is that the hierarchy still exists, as does the rampant self-esteem crisis. As a result, singles of both genders fall into a commitment-phobic warp and become chronic daters, jumping from date to date, trying to work their way up this strange hierarchal design of the UWS. I wonder how people live in this environment year after year and maintain a sense of self and self-worth without becoming too easy or too sad. I don’t know that I am cut out for such a life even though I am willing to return to “the scene” again and again in the hopes of meeting that one person who makes it worthwhile.

To all the singles on the UWS, I wish you the best of lucky and the most unique of praises. I believe that I am capable of a lot, but, in some ways, you are stronger than I am. You endure a strange sort of struggle on a daily basis that I could not withstand. May you all succeed in retaining your sense of self and never feel compelled to compromise yourself in order to feel valued.

I look forward to sharing with you additional insights into the UWS as I uncover them. In time, maybe I will be able to school myself in the ways of the UWS and no longer think of myself as an illiterate stranger in a land of perfectly dressed, albeit, socially inept singles.