You. Cannot. Hesitate.

Smooth’s words-of-wisdom of the week. If you see a cutie on the street, you! cannot! hesitate! Why? First: if you’ve already made eye contact, you’re showing weakness if you don’t go straight for the intro. Second: the advantage of a quick approach is the element of surprise; if you can collect yourself between the time you notice her and the moment you say … whatever it is you’re going to say, then you’re already a million miles ahead of 97% of men in the world who, even if they talk to the occasional stranger, are probably going to flub it because they’ve over-analyzed the situation. What you say is less important than how you say it—or that you say it at all. If you’re clumsy, but pull off an awkward intro. with a knowing smile, she’ll be too overwhelmed by your unexpected self-confidence to focus on your dumb remark. Plus, the more you practice, the better you become.

Today, I hesitated. I had already scored a phone number on the T ride into work (more on that later), but I felt like I had screwed the pooch. So much so, that I went in for seconds.

The young lady in question was a very stylishly-dressed 20-something standing on Summer, texting on her BBerry. I was on my way to the ATM a few yards passed where she had planted herself—to get a $20 bill to buy some Double Bubble gum in my building’s quickie-mart (cash only)—when I noticed her. On my way back, I passed her again. I slowed my pace, caught her eye and …:

Me (looking from her eyes to her BBerry in her hand, as she types): “Hope it’s something good.”

Her (big smile): “It is.”

I blew it. The follow-up, once you’ve overcome the initial anxiety-on-approach (AOA), is crucial. And tough. Whereas you can flub the intro., the follow-up requires very quick-thinking. You may be able to guess what her response will be, but it’s impossible to plan for (Smooth: perhaps we need to develop charts so that we can supplement our fundamental analysis with technical indicators.)

I returned to purchase my 10 pieces of Double Bubble. [WARNING: What follows is not appropriate for minors, asthmatics, anyone with a heart-murmur, or Dane Cook fans.]

Then, two pieces of gum in hand, I walked back to her spot on the sidewalk. She’s still there and saw me coming.

Me: “Are you a gum-chewer?”

Her (quizzical look and slight smile): “I think so.”

Me: “Here, you’ll like this.” (hands over a piece of gum). I had to go to the ATM to get cash to buy gum. It’s good stuff.
Her: “Aw, that’s sweet, thanks.”

Me: “No problem. Do you work around here?”

Her: “No, actually, I’m just visiting. I work for Conde Nast. In New York.”

Me: “Oh. Very cool. So you’re in advertising? Do you have your own account?”

Her: “Yup. I work with jewelry and watch retailers.”

Me: “Oh, nice. Yeah, that makes sense that you’re from New York. I noticed your style when I walked by the first time. It’s refreshing. I don’t know if you’ve noticed that Bostonians don’t know how to dress themselves. Why’d you choose this spot to stand?”

Her (laughs): “Oh, thanks. I’m waiting for a friend. For lunch.”

Me: “Ah, okay. Are you in town for the week?”

Her: “No, unfortunately, just today.”

Me (%*#$): “Oh. Too bad. What time do you leave? Will you be here through tomorrow?”

Her: “Actually, I’m leaving at 3:30.”

Me: “Are you in Boston often?”

Her: “No, not really. This is pretty rare.”

Me: “Oh well. The first time I walked by, I was wishing I’d my phone with me so I could’ve asked for your number. But it’s nice to meet you. What’s your name?”

Her: “Monique. And you?”

Me: “[Captain.]”

Her (big smile): “Well, it was nice to meet you too [Captain]. And thanks for the gum. That was really sweet.”

Me: “Enjoy it. Good luck today.”

And with that, I was off. What will he think of next?