Rarely am I left speechless, but an incident last night did the trick. In the nearly nine years that I’ve lived in NYC, I’ve never had an encounter quite like the one I’m about to tell you. Naturally then, I had no choice but to turn it into fodder for the masses, for two reasons: A) So that you boys can learn something from the rogue behavior of one of your own, and B) So that my entire reading audience can weigh in on whether this guy is brilliant or just straight up insane.

“Picture it, Sicily, 1927…” Just kidding. I couldn’t resist the urge to make a Sophia on “The Golden Girls” reference – which hopefully wasn’t lost on you. Ahem. Sorry, where was I?

Right. I was walking through Manhattan’s Union Square last night around 9pm, having just finished some Christmas shopping errands, on my way to the gym. Suddenly, a guy came up behind me and ran out in front of me, stopping me and waving his hands. “Hold on, wait wait wait – can you stop for a minute?” he asked. “My name is James (changed for privacy), what’s yours? I just saw you walking and thought you were really pretty. So I wanted to come talk to you, I needed to introduce myself,” (or some slight variation, it’s as close as my memory can recall).

While I stood there, dazed and slow blinking in shock, I immediately looked around for either John Quinones from ABC with a camera crew, or for a con artist sidekick who would inevitably be rushing up behind me to steal my wallet any moment now. Maybe it’s a New York thing, but my first impression was to check my pockets. This couldn’t be for real.

Turns out it was. Dude literally ran down a stone cold stranger in the middle of a busy intersection and proceeded to try and pick me up – gym clothes and all. *Note: I’m not the girl who wears cute clothes to the gym, never have been. In fact, I was wearing baggy track pants, an athletic department-issue T-shirt from my college and a hoodie – hardly Workout Barbie attire.

So, since a large part of my interaction with all of you hinges on whether or not you can meet girls in various places (like the grocery store) and how to approach us, how could I in good conscience not turn this into a tutorial? Thus, here are the answers to the questions you’re probably asking right now, in no particular order…

What did he look like? He appeared to be normal, probably late twenties, wearing a button down shirt and overcoat – which he explained by the fact that he’d just gotten out of work. What did I do? I couldn’t stop laughing, and then once I realized he wasn’t kidding I flat-out blurted, “Is this what you do? Did you really just run down a complete stranger?”

Then I informed him of his grievous misfortune in choosing the one female whose job requires that I spin this and possibly use it against him (or not, that’s still up in the air). He thought it was funny, I told him he may not be laughing for that long. And PS, he knows the name of this website, so if you’re reading this, James, let’s see how much of a sense of humor you really have now…

What did we talk about? He lead off by asking me what my nationality is – and choosing correctly (I am ambiguously ethnic, so it was a decent guess). Then he quickly looked for common ground and told me he was partially that nationality as well. He started using anything he could as fodder for conversation – “Oh you’re going to the gym, are you a runner? You look like a runner,” and on and on. How long did this interaction last? About ten minutes, three or so minutes into which he managed to appear disarming enough for me not to run away.

So what happened next? He told me he wanted to take me out for coffee. Boys – take note: he didn’t just loosely throw it out there, he told me when he’d be back from the holidays, and attempted to nail down a date and time. His persistence was actually fairly impressive, and I had to congratulate him on his bravery (even if he is totally full of it). Any guy who pulls a play like this deserves some respect if for no other reason than that it’s such a bold move. I had to tip my hat (and check for my wallet at least two more times).

He asked for my number, upon which time I told him that I don’t give my number out to random strangers in the craziest city in the world. He wouldn’t give up though, and eventually…sigh…I relented. Yup, that’s right, the most critical female of these sorts of moments finally gave in and gave him my digits – the real ones, since I know you’re wondering. Even I can’t believe I did that, actually.

In all honesty, he said, “OK so it’s a date,” and I responded, “Actually it’s more like a case study. I have to figure out where your head was at when you did this, I’m stunned,” which may be most of my motivation should we ever actually speak again.

So now what? Am I crazy? Is he crazy? Am I about to be the victim of some corporate-type, harmless looking con artist, or was he just a guy who saw an opportunity and seized it? You decide, and please weigh in.

I realize how flawed my “he looked normal enough” rationale is, especially since that’s how Ted Bundy got away with picking off dozens of women. But, what he had working in his favor was that he appeared similar to someone I’d be friends with, a fairly regulation NYC male. I am still highly skeptical of his intentions, partially flattered but mostly just not buying it. Again – almost no makeup, hair in a ponytail, Rocky Balboa clothes. But, out of curiosity I stuck around.

So now I flip the script on all of you for once and ask for your feedback. Would you ever try this method, which is essentially the dating equivalent of a cold call? What in the world could possibly be someone’s motivation to do this? Do you think other women would be averse to this or play along, too? Hit up Miss Wingman’s handy dandy comments section or email misswingman@gmail.com and weigh in, please. I have a feeling this is going to be fun… THAT’S WHAT SHE SAID

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