06/14/2012 10:54 am ET Updated Aug 14, 2012

On Dating: New Rules for an Old Game

A week after my 30-ish birthday, I met a guy I knew I should not date -- easy smile, warm eyes, sun-tanned skin, athletic build. Your basic nightmare.

I admired the cheeses he'd ordered; he admired how much I appreciated it. He asked me questions about myself; I didn't ask him any -- I was really into the cheese. And before I knew it, in a crowded wine bar on the West side of Manhattan, I was having one of those moments you only see on shows about single women on the West Side of Manhattan that you believe will never happen to you.


An unattached stranger singling you out? And he's actually attractive? And not drunk? And probably not a serial killer (hopefully)? That never happens. At least not to me, anyway. Investigation Discovery paralyzes me sometimes.

So when he gave me his business card, I seized the opportunity. The ball was in my court, I decided. It may not seem like a big deal, this grand decision. But it was. Normally I'd just let the ball pass, or not even know there was a ball. I've never been good at games, anyway, which is why I usually have a boyfriend. Or date accountants.

But it's the boyfriends who require the most work, a fact I've come to realize in my 30s after the emotionally exhausting relationships of my 20s. But I have not become a pessimist when it comes to dating. I do know that lasting relationships require work.

But who wants to work? It's summertime.

And so when playing the dating game, I show up equipped. The laugh-at-anything. The smile-at-nothing. Plucked eyebrows. Above all, I adhere to the sound advice of my mother, the advice that has less to do with my beauty and more to do with theirs. Never -- ever, she said -- choose a guy with 'the fumes.' He will cheat on you, and you will die. Fumes (my mom is a chemist) = hot looks plus that quality, the 'thing,' that makes men and women alike swoon. Fumes beware. Fumes, no good. He'll get you out of the picture so he and his mistress can move to South America, and you will die.

I trust my mother; she's been married for 40 years. Besides, she knows how to make her own moisturizer. But her advice, while it may have saved me from a cameo on Investigation Discovery, has also saved me from a cameo in my own life.

So what should I do with this business card? I asked my friend who dates (read: sleeps with) a lot more men than I do. That kind of friend is always good to have in times of reconnaissance. You should call him, Friend said.

Once upon a time, I would have. I think of myself as old-fashioned, someone who longs for a simpler time when a man would ask for a woman's phone number; when people actually had to call each other to go places and do things, and you could tell by the sound of someone's voice if they were nervous, interested, constipated. You could just tell things that you can't tell from an email.

Ahh, the nineties.

But I wanted to show that I was fine with the new dating world order. I sent an email -- a perfectly worded and punctuated casual and breezy email. He responded with a date request. At least I thought it was a date request. It was an email. An email that began with "Let me know..." and ended with a smiley face.

Over the course of several days, several equally breezy emails appeared in my inbox. When are you free... Is this time too late... Tuesday at 6:30 it is... great... smiley face. Never a mention of my phone number or even a place to meet. How odd, I thought. Or maybe I've been spoiled with not so attractive men and accountants.

Maybe technology has replaced the rules. Maybe effort is no longer required. Maybe I can change my understanding of the rules.

But then Tuesday came and 6:30 went and then another email.

My phone died, I don't have your number, are you still around?

I unexpectedly lost it. "What?" I yelled at my iPhone, utterly horrified. Around? Where is Around?

And then, a barrage of memories: His sun-tanned skin, just like that first boy who ever kissed me that summer at the community pool, who then pretended it never happened. He handed me his business card but didn't ask me out directly, just like that guy from the cruise who never showed up to that nondescript place, and I wound up missing the midnight buffet. I hate that guy. And in his emails, words like 'great' and that smiley face reminded me of my last boyfriend, whom I dated for three years. I'd like to say I can still hear his voice or see his face -- but I can't. He was a text message addict.

I furiously shut off my phone so I wasn't tempted to respond -- I learned this much from dating disasters of my twenties -- and cursed the gods for not giving me one chance at happiness. I also realized that perhaps my fury was a little excessive, and that it wasn't necessarily about my dating present but rather my dating past, which I couldn't seem to stop repeating. Maybe my problem wasn't that there was a new set of rules to the dating game. Maybe people like me, who used to use telephones, aren't disadvantaged in the new order of things. Maybe the rules never change, no matter how long we play. But if so, where is the fun in that? The next day, I decided to respond to the utter lack of respect and my need to have some fun. So I emailed him.


He responded:

Around...where? Where exactly would I be?

No salutation, no closing. I can roll with this, I thought. I don't need the nineties. Then I got another email:

We were supposed to go out last night

he wrote. No sign of recognition for my sarcasm, or any awareness that he had broken a very old dating rule of actual picking a place to meet. And just then, I was instantly reminded of that cute Princeton guy who wouldn't drive me home because I lived close by, anyway, and so what if it was raining?

Isn't dropping off your date an absolute must? Hasn't it always been? How rude, I thought but never said to him.

I think we are all part of the same old game and always will be. And if that's the case, then so be it. I just wish more people actually knew how to play it.