Just like in the movies

Sorry folks, I've been stressed (and swamped) at work. I haven't been keeping up to date with the blog so I'm posting yesterday's activity. Picture this: A sweltering summer-time stroll home past the angry commuter crowd after a long day at work => unhappy smooth. Half-way home, passing by the locust infestation of commuters, I notice a mirage across the street:

Young woman, white dress, picking though oranges at a fruit stand in the financial district. She is beautiful... in every way. My head is blank as my feet automatically turn and force me to walk over.

My heart's racing (the telltale sign that Captain and I use to measure whether we are truly smitten by a girl or not) but I ignore her and grab the first ripe looking orange I see.

Me: "Wait a minute, take this one, I mean it."

Her: "Oh, I think the one I have is ok." She smiles. I'm in the door. She starts to turn away.

Me: "No, I like this one better, I insist." I place the orange in her hand. Then I turn and grab a small carton of strawberries. "You need these too!," I tell her. She's laughing now.

Her: "Seriously, I just came for the orange."

Me: "Well, I understand, but these strawberries look awesome. They're on me. What's your name by the way?"

Her: "I'm ____. You're funny."

5 minutes later I walked away with her phone number. As Captain pointed out, don't hesitate. And it really doesn't matter what you say as long as you deliver it with confidence and have fun. I just replicated the cheesiest "fruit stand/supermarket" movie pick-up scene. So what? The corniest pick-up move in the real world beats meeting girls on the internet. I'm sure women feel the same way.

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?

Taking it to the Lionesses’ Den

This post had been removed after it caused a falling out with a friend. Here it is reposted, unformatted:

Last night was a late-night game. I got out of the pool around 7:30 pm and began to head home. Before I got on the T at Park, I made a few calls to see if anyone would like to join me for a drink. I needed to reward myself for completing two articles for the corporate newsletter that I edit. Game on. I called my friend J. She’s great. An ENTP (or J … I forget. I have a man-crush on Carl Jung…) and feisty. She can drink me under the table and still look good, wth? (I learned the secret to this metabolic miracle during the course of the evening: women, as I suspected, just don’t eat on nights that they go out drinking). J was already 2 bottles of champaign in at Ivy, a cool bar-bistro on Temple Place. In her defense, it was a champaign tasting night. The tasting was in the bar’s basement, and as I descended the stairs, all I could see were pairs upon pairs of stylish high heels. “This could hurt,” I thought; “Best just to have fun.” I began envisioning this as my opportunity to explain my philosophy on love: “‘If you blow chunks and she comes back, she's yours. But if you spew and she bolts, then it was never meant to be.’ Discuss.” I got there just in time to steal a glass from bottle number three, that our waiter (who J’s friends had generously nick-named “Dipples”) brought around. I dragged up a seat and squeezed in between J’s table of friends—D (somewhat engaged but with a raging appetite for ginger-love that I’d soon discover…), K (married, lucky guy), and K2 (seriously single, sexy, and self-assured)—and a table of two friendly older women out on the town. Following the drinks and hors d’oeuvres and Dipples, I was in clearly the main attraction, and I had to make an ironic effort to play it cool. So far so good. I got an update from J and then was corralled into conversation with the ladies to my right. Having just exited a relationship with a 43 year old (sure to be one of the loves of my life, sincerely), I was decidedly not going to try for a throw in the hay, and I tried to extricate myself. Thankfully, my cute companions came to my rescue. K, to my left, quickly informed me that she is married. No problem. Her southern charm was endearing, and we struck up a conversation about the importance of matching snowboard pants, boots, and jackets. One won-over, two-to-go. D., diagonally across from me, next to J., was a harder nut to crack. In fact, I’m not sure I did. She was all sass. The champaign was getting the better of her, and her first words to me were “Can I call you ginge?” (I cringed. Anything but that. Fire-crotch would have been an improvement.) “Sure” I said. That set the tone. J knew about my blog, and I was pressed to describe Game: On Boston to my new acquaintances. It went over well. I was very careful to lay out the ground rules: no vulgarity / cruelty / crudity, once-a-day impromptu talk to an attractive woman who you’d otherwise pass by, game-over if something comes of these conversations and things get serious. D. gave me mild grief, but generally didn’t put me into a bind. I’d neutralized her, and this was the best outcome I could hope for. We continued to drink, moving to the upstairs bar. I began to consider trying to cap the night with K2’s phone number. I’d have to wait and see how things progressed. Upstairs, another ginger and his friend were having a beer next to us at the bar. D. was in full man-eater mode, and repeatedly approached the guy to squeeze his muscles—returning to tell us that they felt like spaghetti-O’s al-dente (yes, you read that correctly … it’s meant as a compliment). D. threw up a few temporary hurdles, refusing to tell me what she did, except to insist that she “sold drugs and stripped.” The best way to deal with this sort of sass is to day nothing. It’s like avoiding getting mauled by a bear; you must play dead (or dumb: I asked her what she did a solid 5 times, knowing I’d get the same response every time). Hours after I’d arrived, D and K had stumbled home, and J, K2, and I were left talking at the bar. K2 and J are proudly independent, and we discussed their views on marriage (“not for us”) and boyfriend/girlfriend “titles” (to be avoided). K2 does have a guy, but she insisted she is single, and I liked that; what little I learned about her current guy lead me to think that I might have a chance of securing a great date with her (I’m repeating myself). J was the next to fall, and K2 thankfully didn’t need to have a friend as a crutch and stayed to talk about the economy and other exciting (seriously thought) big-picture items. As we were preparing to take off, she mentioned her college reunion approaching and suggested she might like the company. I said great and offered to see what else is happening in the area then. We exchanged numbers, and if she doesn’t regret it, I’ll call her to organize something. The lionesses’ den is the way to go. Thanks ladies ,).

A Brush with Hotness

Before I recount the rest of the weekend (and I apologize to our loyal readers for the delay; when you wait until 5-drinks-in on a Saturday night to make your move, writing is the furthest thing from your mind at the end), I got off to an early start today.

This is too easy.

Smooth and I are facing a steep learning curve, but we’re finding there are simple short-cuts to making an entry with a(n attractive female) stranger. Today I discovered one of them, quite by accident.

Scene: riding the T (trolley, green line) to work. Approx. 8:30 am. No one is happy. At least most people are clean and odor-free. I’m standing in the handicapped alcove (laugh it up, I’m a gentleman and always stand), leaning against the window. At Stop X, “High Maintenance Bosom” (HMB) gets on. HMB looks exactly as her nick-name suggests: very well-put-together—possessing certain flattering physical attributes—but wearing the mark of maintenance: more brand names than a guy can count (quick aside: I prefer well-dressed women without the ostentation). No matter, she’d achieved her desired effect: my eyes wandered.

At first, HMB stood opposite me, back-facing, and I did my best not to stare … wondering if a cute musician a few feet off would tell me what instrument she was carrying. Eventually, HMB sat in the seat at my elbow. “Well, no chance talking to her” I thought. Wrong.

Five minutes later, the T jerked to a hard stop and my elbow brushed HMB’s perfectly-coiffed hair (::imitates Marlon Brando “…the horror…the horror…”::). She quickly reached back to put two mussed hairs in place and gave me a look that said “these nails may look good now, but do that again, and you’ll curse the last time you thanked God for your manhood”.

I couldn’t let her glare phase me. I had my “in”.

We both got off at Park. As she crossed onto Winter, I made my move.

Me: “Hey (loud enough to hear with her ear-buds on), I’m sorry I elbowed you on the train.”

Her: “Don’t worry about it; I didn’t even notice” (she’s pulled one ear-bud out and makes a motion to put it back on, so I try again)

Me: “Do you work around here?”

Her: “Yeah, I work on X Street. I would usually switch lines, but it’s such a nice day, I decided to walk.”

The conversation lasted to my office, a solid 5 minutes. By the end, we were talking her last spring break (she went to school in Florida) and the bars closest to her office. We’d exchanged job info. She does analysis for a venture firm, and I—because of my work—know a little something about venture and private equity, was surprised. No doubt she was bright and articulate, but my impression of her was that she was not an intellectual: fine for a fun night out, but not regular dating potential. But I like to be proved wrong.

We parted outside my office:

Me: “So, can I get you name and your number, and you can invite me to one of your office happy hours?”

Her: “My name is Emma … actually, I have a boyfriend.”

Me: “That’s too bad. (remembering my manners) Too bad for me, that is … it’s great for him.”

Her (smiling): “Well, have a good day.”

Me: “See you around.”

We break the grass barrier

Well, this is a weird one. Captain and I are taking a break from work, cruising around the financial district in the afternoon. We grabbed lunch yesterday in P.O. Square and noticed that the place was mobbed with attractive girls lounging on the immaculate lawn in various reposes -- they are either reading a book, eating lunch, or lying down soaking up some rare Boston sun. And of course, around the perimeter of the lawn are the usual suspects...middle aged, paunchy brokers from Merrill Lynch drooling and thinking lewd thoughts as they stare at the girls. None of them have the balls (or game) to actually approach any of the women. We instantly decide we've found a new spot to work but realize that it's intimidating to walk up to these girls and sit down. After all, you're going to have to get up immediately if you make them uncomfortable and the whole world will see you getting shot down. We decide that making a move here even one-ups stopping a girl on the street.

Fast forward to today. We decide to return to P.O. Square around 3pm to see who's still out here in the late afternoon. The answer: absolutely no one. Apparently it really is only the place to see and be seen during lunchtime. Panning to our left, we spot one lone girl, with her back to us, lying in the grass. She's wearing tights (the sort that girls wear to the gym) and a t-shirt, and is lying on her side as though she were in a bed. She even appears to be sleeping. And she looks hot from our angle.

I tell Captain we have to do it. There are enough people watching as we walk across the grass and around to face her that this will be embarrassing if we flame out, but who gives a shit. Call this the ultimate practice run.

As we get closer and kneel down facing her we notice she has sunglasses on and iPod earbuds in. She's in for a shock:

Me: "Excuse me, we just wanted to stop by and let you know you're late for your afternoon appointment." No response. Four seconds later she looks up. Startled, she takes off her sunglasses and earbuds and says "What?"

I repeat my ridiculous intro line and Captain chimes in, "Yeah, you know we figured we should wake you up."

Her: "Oh I should get up anyway." She's surprised by us but not pissed...seems more intrigued.

Me: "We figured you were a hot-shot lawyer up on the 15th floor over there and you were sleeping through your afternoon appointment. Don't you have to get back up there and change into your power suit?"

Her: [Smiling] "No I just work over at the gym there, that's all."

Captain: "Equinox?"

Her: "Yep, that's where I am."

Me: "We're just kidding around. We figured we'd come over and say hi. Have a good afternoon."

Captain: "We'll see you around."

Her: "OK, bye."

Wow that was a surprisingly relaxing conversation. It was apparent to us as we walked away that we probably could have gotten her number. I guess it's fair to say that you can meet women in almost any circumstance and pull it off if you're comfortable in your own skin and don't care about potentially getting shot down in front of people.

Three Times a Lady ... Four Times, a Masshole?

I'm back after a weekend hiatus (sun stroke), and so it's rather inexcusable that this post will be rushed ... but I've only got 15 minutes (before I get sauced with C.---a lovely 23 who just wants to have fun, for now), and typically, I like to take care when I write.

So, Smooth and I ventured out again on Saturday night. We started at Minibar (Minibar: I'll accept payment in nickles and kierkegaards ... yes, I am a gold bug with a fetish for Thomas Jefferson). The scene was swank-yuppie, and had there been more than one pair of single women there, we would have stuck around. As it was, there were lots of Euro-types (not quite trash, although it was early), and a gaggle of about 7 women seated at one table. We decided then and there that women in those numbers are out of the question. They'll play with you like a cat with a mouse for kicks, but that never ends well ... I'd go so far as to say the best the mouse can hope for is scurrying in circles while dragging his bruised and bloody body further than a sure escape: death. If you're going to go in for that kind of treatment, you should be prepared to go out like a rock star---fly open and all---and we had only had one drink a piece.

Anyway, cutting to the chase. We decided to saunter outside and take in the bar from a different angle (big open windows). To do so, we had to commit to eating, and this allowed us to flirt with the waitress mildly, and once seated, we realized that we didn't have to eat; however, we had bought ourselves some time to plot the next move.

I decided that the (other) waitress was well worthwhile, and the only quarry in sight, I'd try a line and hope for the best. Here's the conversation as best as I can recollect....

(Waitress arrives to take order) Her: "What can I get for you guys?" (good eye contact, nice smile)

Me: "Actually, we didn't really want anything to eat. I was just looking for an excuse to talk to you. I hope you don't mind."

Her (smiling): "Oh, no, but I live with my boyfriend."

Me: "Well, I hope he knows that he's a lucky guy. I had to give it a shot. You're really cute; that's a great dress."

Her: "Well, thank you. I guess, have a good night?"

Us: "Goodnight."

Smooth, feel free to correct me where I'm wrong. Still to come ... the bachelorette parties and the porn star.

I scare Church Girl, then redeem myself (sort of)

Today I went for what Captain and I have decided is the toughest challenge: stopping a girl who is walking down the street and engaging her in conversation. You have to interrupt someone who is moving and probably doesn't want some stranger talking to her, all for the sake of finding that rare, hot single girl who is looking to meet someone and is also amenable to being approached out-of-the-blue (for all you math majors out there, you could represent what I'm talking about with a Venn diagram that highlights the challenge).

Anyway, back to today: I walk into the Park St. Church close to the end of the service to scope out the scene. Actually, the rock band there kicks ass so it's worth it just to listen to some live music.

Peripheral vision kicks-in and I spot a girl who seems quite attractive in a pew near the back of the Church. I plan on saying hi as she walks by but she leaves so quickly when the service ends that I literally have to chase her downstairs and out on the street. This is going to be awkward:

Me: "Hey that was a great service, right?" (as I catch up to her). She's obviously a bit taken aback but doesn't break stride, heading straight for the T-station.

Her: "Yeah, it was."

Me: "Can't beat that rock back too! Where you headed?"

Her: "Home."

I'm totally out of time. She has neither smiled nor broken stride and we're almost at the door to the Park St. station.

Me: "Well it was nice to meet you; I'll see you around."

Her: "Sure."

Oh well. The combination of me freaking her out a little and her being less than friendly did not mix. Shot down hard.

An hour later I'm crossing Arlington St. headed into the public gardens when I spot a smokeshow blond in front of me. What the hell. Once I catch up to her I use a dumb intro: "Hey, how's it going?" She turns, smiles, and stops. I end up talking to her for five minutes or so. She's friendly, but unfortunately from out of town and leaving today. At least I end on a high note, with good karma.