Category: making the first move


August 12th, 2011 — 1:05pm

When it comes to so-called dating rules, one of the most tried and true is waiting for the guy to make the first move.  I’m usually a big believer in this approach – though a recent conversation found me considering exceptions to it.

Over drinks at Midtown watering hole Sutton Place, galpal N shared her conundrum about the cute guy she encountered at a bar. The friend N was with could see she was smitten and opted to be bold for her, walking over to Mr. Cute and telling him he should ask N out. He immediately approached N – and gave her his number.  N proceeded to suggest they go out sometime, then immediately questioned having taken the initiative.

I empathized with her completely. Female or not, going out on a limb when you first meet someone isn’t easy. Having said that, why stand on ceremony if you’re interested enough to act on it? Inspired by N’s courage, I opted to throw a little caution to the wind myself.

Months ago, OkCupid matched me with a former colleague with whom I had a contentious (to the say the least) relationship. Ignoring our complicated history, he took a chance and invited me out for dinner. Sensing my lingering reticence, he gave me his card at the evening’s end – making it clear the ball was now in my court.

So I emailed him and proposed meeting for drinks, holding my breath a little as I hit send – and appreciating a little more what men go through when they do the asking.

He responded with an enthusiastic yes. Sometimes, it pays to break the rules.

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December 20th, 2009 — 12:05am


Not too long ago, I did a post about prompted by repeatedly seeing a certain guy there. A recent encounter with him got me to thinking how absence doesn’t always make the heart grow fonder.

As I mentioned before, this guy has made a habit of staring at me. Ironically, after deciding to finally break the ice and say hello, I didn’t run into him for about a month.

My fabulous trainer Crystal, however, did see Mr. Mysterious. She said he would look at her expectantly, like he was waiting to see if I was with her. I’m not so sure, especially after our bizarre exchange the other day.

He walked past Crystal and me to the other side of the floor. About two minutes later, he circled back and approached us — literally stepping between Crystal and I, gazing intently at me. I gave him my best, most inviting smile…and he just kept on walking.

Now I can certainly appreciate being the shy, silent type (I’ve dated a few of those). And I can also understand treading gingerly before making the first move. What baffles me is spending months skirting thisclose to doing so and not following through.

At the risk of sounding like a ‘rules’ girl, I think sometimes a man just needs to man up and do something. If he can’t work up the courage to do it at the beginning, it’s only downhill from there.

Who knows? Maybe Mystery Guy just enjoys staring.

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December 19th, 2009 — 7:05pm


Not too long ago, I did a post about prompted by repeatedly seeing a certain guy there. A recent encounter with him got me to thinking how absence doesn’t always make the heart grow fonder.

As I mentioned before, this guy has made a habit of staring at me. Ironically, after deciding to finally break the ice and say hello, I didn’t run into him for about a month.

My fabulous trainer Crystal, however, did see Mr. Mysterious. She said he would look at her expectantly, like he was waiting to see if I was with her. I’m not so sure, especially after our bizarre exchange the other day.

He walked past Crystal and me to the other side of the floor. About two minutes later, he circled back and approached us — literally stepping between Crystal and I, gazing intently at me. I gave him my best, most inviting smile…and he just kept on walking.

Now I can certainly appreciate being the shy, silent type (I’ve dated a few of those). And I can also understand treading gingerly before making the first move. What baffles me is spending months skirting thisclose to doing so and not following through.

At the risk of sounding like a ‘rules’ girl, I think sometimes a man just needs to man up and do something. If he can’t work up the courage to do it at the beginning, it’s only downhill from there.

Who knows? Maybe Mystery Guy just enjoys staring.

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May 15th, 2009 — 10:51pm

One of the big surprises of thirtysomething singlehood — apart from the surprise of still being single — is the attitude shift that happens when it comes to dating.

Call it a learning curve or mellowing with age, but the rules of dating become more bendable as you get older — a welcome twist I’m rediscovering with Cedric.

The NY International Auto Show: Where Cedric and I first crossed paths

Cedric and I at a gala preview for the New York Auto Show. Smart, adorable and Swiss born (yes, he has a sexy accent), he intrigued me right away.

We ended up sharing a few tipsy kisses and the next day, I found myself emailing Cedric to wish him well on his imminent vacation. He replied immediately, which encouraged me to initiate contact again after he returned a few weeks later.

During my twenties, making the first move after meeting a guy was unfathomable to me. After all, popular wisdom says that if a man is interested, he’ll do the follow up, right?

While I’m still inclined to agree with that particular rule, I’m also finding that very liberating to depart from tradition and see what happens.

What’s happened here is Cedric asked me out and we met for drinks last week. The easy banter between us was still the same, the kissing still exhilarating. We’re seeing each other again on Monday.

It’s too soon to tell if all this chemistry will amount to more than a passing flirtation. Then again, isn’t that what breaking the rules is all about?

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May 15th, 2009 — 5:51pm

One of the big surprises of thirtysomething singlehood — apart from the surprise of still being single — is the attitude shift that happens when it comes to dating.

Call it a learning curve or mellowing with age, but the rules of dating become more bendable as you get older — a welcome twist I’m rediscovering with Cedric.

The NY International Auto Show: Where Cedric and I first crossed paths

Cedric and I at a gala preview for the New York Auto Show. Smart, adorable and Swiss born (yes, he has a sexy accent), he intrigued me right away.

We ended up sharing a few tipsy kisses and the next day, I found myself emailing Cedric to wish him well on his imminent vacation. He replied immediately, which encouraged me to initiate contact again after he returned a few weeks later.

During my twenties, making the first move after meeting a guy was unfathomable to me. After all, popular wisdom says that if a man is interested, he’ll do the follow up, right?

While I’m still inclined to agree with that particular rule, I’m also finding that very liberating to depart from tradition and see what happens.

What’s happened here is Cedric asked me out and we met for drinks last week. The easy banter between us was still the same, the kissing still exhilarating. We’re seeing each other again on Monday.

It’s too soon to tell if all this chemistry will amount to more than a passing flirtation. Then again, isn’t that what breaking the rules is all about?

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