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.