Great Expectations

“In a city of great expectations, is it time to settle for what you can get?”
 — Carrie Bradshaw

If there’s one thing New York never falls short on, it’s choices. Hungry? One could conceivably live a lifetime here without eating at the same place twice, what with the sheer number of dining choices plus the constant opening, shuttering, popping up and redesigning of restaurants. Bored? There’s no shortfall of concerts, parties, shows and festivals; the problem is not so much what to do but how to fit everything into 24 hours.

So you can imagine what it’s like when it comes to dating.

Depending on what you’re looking for, dating in New York can make you feel like a kid in a candy store or a parched wanderer in a desert coming across nothing but mirages. Even if you’re not a total jackass, the seemingly infinite choices renders most people paralyzed and unable to make a firm decision. A recent article in the New Yorker put it quite well:

“When there is something better out there, you can’t help trying to find it. You fall prey to the tyranny of choice — the idea that people, when faced with too many options, find it harder to make a selection. If you are trying to choose a boyfriend out of a herd of thousands, you may choose none of them. Or you see someone until someone better comes along. The term for this is “trading up.” It can lead you to think that your opportunities are virtually infinite, and therefore to question what you have.”

On the other end of the spectrum, there are those who are tired of the seeming futility of it all and who just want to get off the damn dating carousel. The same article explains this feeling as such:

“If you really are eager, to say nothing of desperate, for a long-term partner you may have to contend with something else — the tyranny of unwitting compromise … The people who are looking may not be the people you are looking for … Some people are too picky, and others aren’t picky enough. Some hitters swing at every first pitch, and others always strike out looking.”

When you’ve spent some time in the dating loop, it becomes tricky not to fall prey to either of the two. I constantly encounter men and women who seem to be perpetually looking over their date’s shoulder, just in case someone better walks in between the amuse-bouche and first course.

Almost as frequently, however, you see people talk themselves into relationships, resigned to the thought that anything is better than nothing. Once I began hovering around the 30-year-old mark, I found myself at greater risk of falling into this trap, in danger of getting pushed in at a moment of weakness by some thoughtless remark. I don’t know why but people now seem to find it acceptable to say things to me like “Are you ever going to get married?” or “Don’t you get scared that you’ll never get married?” While I’m probably entitled to respond with “That’s really none of your goddamn business”, I usually end up explaining that if I wanted to get married just for the sake of getting married, I’m sure I could find some other desperate person out there willing to hold hands while we place our heads under the axe of that tyrant called compromise.

Lately, my conviction has grown stronger that it is worth it to hold out for something that defies both tyrannies. That something was once spelled out for me by Mike, my dear friend Che’s amazing husband, in the simplest yet most crystal clear terms. As I launched into my latest dating saga in the hope that he could decode the most recent confounding guy’s mysterious tactical maneuvers, he stopped me in mid-sentence.

“Drop him.”
“What? But you haven’t even heard the whole story yet!” 
“I don’t need to. You deserve someone who’s crazy about you. Plain and simple.”

I stood there with mouth agape for a few seconds until the truth of what he said sank in. He’s right. At the end of the day, that’s what it’s about. The only reason to be together is if you’re both crazy about each other. If one of you is still looking over the other’s shoulder, or if the only thing that binds you is the fear of missing the boat, that’s simply not enough. 
The greater the expectation, the greater the reward. I believe it.

Originally published at