Gold-digging on Washington St.

I love Washington St. in downtown Boston. I walk past it every day and marvel at how the business crowd in suits passes by the gang-banging crowd from Roxbury without incident. They both ignore each other, which is probably for the best.

Captain and I have window seats inside Boston Common Coffee Co. Perched in our chairs, we people watch the Washington St. crowd, attempting to tell passer-by's life stories from their attire and gait. Then she walks by: tan... black halter-top... black suit pants that her ass can barely squeeze into... shaking what she's got... dragging along a suitcase. Captain starts to drool. I tell him to snap out of it and he tells me to get up. Boy-cut, lesbian barista girl overhears us and laughs as we bolt out of the store and follow our target down the street.

She stops by Macy's and we catch up to her. She's obviously lost. Captain glides by her and turns to face her as though he just saw her for the first time through his peripheral vision. She has no idea we stalked her from the coffee shop down the street.

Captain: "Do you need help finding someplace?"

Her: "I'm looking for this restaurant that I'm applying for a waitressing position at." She motions at a menu/drink list she's carrying to some fancy (cheesy?) place located nearby.

I take a closer look at her. She is very tan, very Italian looking, with bright yellow pumps on her feet. Her overall outfit is certainly not classy but not toooo trashy either. I wonder what she wears on weekend nights.

Me: "Need help with your suitcase?"

Her: "Oh no thanks, I have three heads in here. I mean mannequin heads for practicing cutting hair. I go to Blaine for hairdressing, but I can also do nails and other things. You guys should come in; you both have nice hair -- I'll give you cuts for $5."

Oh boy, here we go.

Me: "That's awesome. Blaine is the best school in the country for hair. Good for you."

Captain: "Nice, we'll come in for cuts. Are you from around here?"

Her: "I'm from Weston. I grew up there and but went to Catholic school." [bullshit. She's from Revere or Everett or Medford. Winthrop at best. I suppose she's lying to appear upper-crust.]

The conversation deteriorates from here. Among other things, she tells us she's of Czech heritage (yeah, right). I give her my business card and tell her to call and we'll find a time to get haircuts. We walk off.

Captain: "Gold-digger, looking to pawn some sucker. That's not us."

Church -- Rewound

Captain and I are supposed to attend service at a small, non-denominational church in the Back Bay. How did we hear about this church, you ask? Long story, but the short answer is that we were accosted by a bachelorette party last weekend at Dillon's on Boylston St. Literally. I mean, we had seats at the bar, were hemmed in by 6 girls (3 hot, 3 not), and among other things received an invite to go to church with them. Of course we agreed.

I made an ass of myself the last time I tried to make a move at church so hopefully today goes more smoothly (no pun intended). It's an 11am service but looks like Captain has not slept in his place and cannot extricate himself from present company to join me, so I'm flying solo. The service is actually quite entertaining. Pastor X is young and has an alternative, revival spirit. I'm feeling the love. Two very attractive girls in sundresses walk in late and grab seats up front. Now I' m in love. Wow, that was fast. I have my mission.

The service ends and everyone's mingling. I head out and shake hands with Pastor X. He's a "cool and froody" kind of guy, to quote Zaphod from the Hitchhiker's Guide. I instinctively like him. I head back into the antechamber and find Sundress 1 and Sundress 2 walking by, laughing. As they pass me I make some sort of harmless, ridiculous comment. They laugh. I accompany them outside. 5 minutes later I have the email address of Sundress 1. I have redeemed myself. Halleluja!

I'll take a medium iced

These next two posts will be short as I am way behind on my blogging. Another Smooth and Captain expedition:

We enter the local indie coffee shop next to our office for a mid-afternoon jolt. I've spoken to a barista who sometimes works the afternoon shift (cute, but not hot) a couple of times now and notice she's here. The place is practically empty. We start talking to her. She's interested in chit-chatting with us. Captain gets his coffee. She keeps talking, talking, talking. She has an empty plastic cup in her hand for me but can't stop talking and get around to making my drink. Captain finishes his coffee and exits to make a phone call to a female friend. She finally makes my drink. Other customers enter and pause to reflect on the menu. I have my out, and she writes her number down for me on an order slip before I slip away.

Postscript: I've texted back and forth with her for the past 2 days. She is incredibly immature (but I suppose no more so than your average 21 year old female). I have yet to meet her but am less and less interested with each passing text.

The Bottomless Money Pit is My New Best Friend

Quick recap of yesterday's success:

Girl on T. Me. On the T also. Reading a book. Snatching glances at girl. Girl rolls her eyes (At what? Unclear.) T stops. As usual. For 5 minutes outside of Park Street. I make remark, to girl, about the driver texting her dealer for a fresh crack rock. (Actually, this didn't happen; I said "It would be faster to walk to Park Street." True.) Girl and I got off the T and walk and talk most of the way to my office. I got girl's #. The end.

The movies: Part II

This is quite funny (and 100% true for all you miserable haters out there). I just met a girl in the most Norman Rockwell (Read: Saturday Evening Post)/1950s Hollywood way possible: I helped her pick up a bunch of blueberries that she had spilt all over the ground outside of the supermarket. No joke. I mean seriously, if I were going to make up a post, I wouldn't pick something so cheesy....I'd rather tell a tale that involves a tuxedo, a high-speed chase, a gun, a cocktail dress, and venom (you know, the kind that some girls have in their bloodstream).

Back to tonight. I'm rounding the corner, leaving my local Whole Foods when I spot a petite girl, dressed in gym gear, kneeling over a broken grocery bag trying to pick up all of the blueberries that had fallen out of her bag.

What would you do if you came across this situation? I'll tell you what most guys in Boston would do...keep walking.

After helping her pick up the berries, I realized she was still overwhelmed with heavy bags, and helped her carry one of them home. Turns out she's your typical East Coast girl -- prep school, nice, private New England college, financial sector job, etc. I'll email her and invite her on a run this weekend.

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.

We upset the 90's dance queens

It's the first nice Friday evening in about a month, so Captain and I decide to grab a drink after dinner. There's nothing happening in the area around the Publick House in Brookline so we decide to drive across to Allston -- the land of hipsters, dive bars, and garbage-strewn streets. We park and walk past The White Horse Tavern and Sunset Grill, debating where to go when suddenly I remember... there's a place somewhere around here that I went to a couple of times with my ex-girlfriend and her friends that had a decent number of single girls. Oh yeah, the Common Ground. Vague memories come back to me of an 80's night that I attended over there, where the hipsters had turned up dressed up as Rainbow Brite and G.I. Joe.

Turns out I wasn't too far off the mark. We enter the Common Ground to find out that it's 90's night tonight. Great. Get ready for "Ice Ice Baby".

10 minutes after we enter a gaggle of four young women stroll by us and we end up making inane small-talk for 20 minutes before it becomes clear to us that they came here on a mission -- they are here to dance. And so all six of us hit the dance floor. Neither Captain nor I are Rico Suave when it comes to dancing but we manage to do the white boy shuffle for a little while. Then we start getting tired. We had a good time but neither one of us is excited enough to stick around until the end of the night here (Captain has a girl waiting for him and I'm not interested enough to pull out my cell phone).

We say goodnight, and as we turn to leave, we receive an utter look of disappointment from the girls. What the hell? These girls are actually upset that we're leaving. Turns out that when the ratio of girls to guys is 70:30 it is a big deal to ditch your "dates" and bounce. OK, now we know.

Ghetto Fabulous

I am about to do something that I would never normally do unless I was completely shit-canned wasted. I broke the rules by not blogging yesterday, and my excuse has been that I've spent too much time with a 32 year-old (with the body of a 24 year-old; trust me you would spend time with her too). Anyway, I've been derelict from the perspective of Game: On Boston so it's time to get back in shape.

Back to this afternoon: I'm walking back from grabbing lunch downtown when I spot a girl with an unbelievable body standing outside of a doorway on Summer Street (in case you haven't gotten the idea I'm more of a body guy than a face guy). But...she is also the ultimate stereotypical Latino chick: her name (or her baby daddy's?) is tattooed in large, flowing script on her neck; she's wearing too-tight, faded jeans; her hair is pulled back tight and, you guessed it, she has those huge, gaudy hoop earrings hanging from her earlobes. To further set the stage, I am wearing a button down Charles Tyrwhitt shirt, dress pants, and matching Johnston & Murphy shoes/belt. This should be interesting.

I slow down, lean back, and smile:

Me: "Hey what's happening girl?" [Yes, I just said that]

Her: "Whaat?"

Me: "Uh, I mean, it's awesome out here, are you on your lunch break or something?"

Her: "No, I cut hair. I just stepped outside." She motions to her left and I see the hair salon next to her.

I attempt to lay back a little and try not to be the office-boy stiff that I must look like to her.

Me: "Cool. I should come by y'alls place sometime for a fade" [fuck, I think I just mixed up country and ghetto in one sentence. This is not going well]

Her: "Yeah, ok that would be nice, you should." She smiles.

Me: "I will. Listen, why don't you give me your number and I'll call you sometime." [You gotta be direct with the Latin and Black chicks, right? They give you props for that, I think...]

Her: "I can't, my boyfriend wouldn't like that."

Me: "Alright, it was nice to meet you," as I scurry away picturing a 6'4" black dude named Tyrone as her boyfriend. He would probably squash me like a bug if he knew I was angling his girl. Time to go back to my existence as an office cockroach.

Hail Mary

He swings! and... Whiff!

On my way down to the lobby after work Monday night, I rode in the elevator with a very cute 30-ish something from Sapphire Recruiters, a small tech. recruiting company. We made some small talk about the Michael Jackson funeral and CNN's coverage and were still walking and talking out the door of the building together when she went right and I went left, to the gym. I've been kicking myself for 2 days for not having asked for your number.

Well, Game On (Wayne).

Today, I wrote my name, number, and email on a scrap of paper (ridiculous, I know, even as a slave for attorneys at SKADDEN I had business cards ... this will eliminate any small chance I might have had of getting a date) and took a trip to floor 10, Sapphire's office.

Actually, I did this twice. The first time no one was at the front desk, and I rang a bell (a bell?! really? REALLY?). That was unnerving; thankfully, the economy doesn't concern them, and no one came forth to enjoy the spectacle I was inviting. The second time, 30 min. later, the front desk admin. was there (also smoking hot; I worried for a second that I didn't remember what elevator chick looked like...), and...

Me: "I talked to a young woman on the elevator the other day about Sapphire, and I was hoping I could see her."

Her: "Do you know her name?"

Me: "No."

Her: "Was she a blond or brunette?"

Me: "Tall and blond."

Her: "Oh, okay, let me go check." (looking quizzical, she disappears into an office down the hall for a painfully long half minute)

Her: (back) "She's on a conference call with Maureen, but is there a message I can leave?"

Me: (having guessed that front desk chic told hot blond "Hey, there's some strange ginger here to see you. Should I call Eric Cartman and have him taken away to the internment camps?") "No; I just wanted to give her this." (I produced the folded paper with my info.) "I met her on the elevator the other day, and I was kicking myself for not giving her my number ... or getting hers. (sheepishly) Sorry if this seems creepy."

Her: (seemingly surprised in a good way and smiling good-naturedly) "I'll make sure she gets it. Have a good day."

We'll see what happens. I'm not optimistic. Should I go back down later this week?

What a Mess

My conspicuous 2 day absence from this blog, in clear violation of the rules, has an explanation (if not an excuse). Tuesday night was a major debacle in my dating history. The night started relatively well---a little shakey, but nothing that wasn't easily overcome; I met a girl I'd emailed a few times over Match.com at Bukowski's, a great hole in the wall beer oasis in downtown Boston (named after the "poet" who, if my date's info. is good, was basically a second-rate Nabokov who actually stuck his dirty old penis in all of the young girls he seduced ... so that he could dump them, go on a whiskey bender, and put the stories in ink for posterity. Only in America).

Any way, long-short: Sappers (as I'll call her) was VERY intelligent. This quality alone made me swoon a little, despite her size (very curvy) which generally isn't for me. To top it off, she had a gorgeous smile and delicate laugh. Despite her drinking me under the table (by my count, at night's end, she'd had 6 beers ... at least 3 of which were 22 oz.), we managed to carry on an interesting enough conversation to bring us to a second bar, The Pour House.

This is when the date began to self-destruct.

Sappers is a teacher. To be precise, she's a behavior modification specialist. These may not have been the exact words she used to describe her work, but to the best of my recollection, she did say:

"I read Brave New World for class a second time, and I realized I admired the way that society was organized." and "Basically, I manipulate people for a living."

Now, before you say, "Captain, perhaps you should have realized at the outset that Sappers was ... how shall I put this ... CRAZY! and you should have cut your losses with a long shit in the W.C., which you could have subsequently described to her in great detail." Well, perhaps. But differences of opinion are what make living worthwhile, and she defended her point of view admirably, so I gave it a go.

Unfortunately, differences of opinion sank this date. Toward the end (when the six beers she'd pounded started to catch up with her?), I innocently informed her that I plan on homeschooling my kids. My justification is less important than her reaction (I'm trying to keep politics off of this blog, since it's my hobby-horse). Needless-to-say, her head nearly starting spinning and vomiting in every direction. I calmly tried to bring her around to my P.O.V., but it was too late. She'd decided that I was a future "child abuser", and we parted.

Lesson learned: if you're going to date school teachers, don't quote Paul Simon, Mark Twain, Albert Einstein or any other luminary who says something to the effect of "I never let schooling interfere with my education."

Same place, same time

Deja vu. Cute girl, doing some ridiculous girl-style leg exercise where she kicks out her leg as she's facing the mirror, elbows down on the mat. This will be embarrassing to ask, but what the hell. I start talking to her while I'm doing a set of lunges. "So is that an abs routine or more of a legs thing," I ask in a perplexed tone. She laughs. "It's actually my butt I'm working on." I smile and ask her to take me through it. She's really good natured about it and I pick up an exercise that actually does work your ass believe it or not. I get her name before I leave. Much better vibe than yesterday. Laundry time now... what a let down.

Telegrams from the Gym

I've been stalking a girl at my gym. Before you think I'm a wacko, let me clarify. By stalking, I mean showing up everyday hoping she'll be there. That's all. I think I said a few words to her once figuring I'd see her a lot but it's been a few weeks and she's been on a different schedule than me.

She's here tonight, on an elliptical machine. I'm planning on a long run later tonight so decide to do some simple shoulders and abs routines until I get a chance to say hi. Half an hour later I saunter over and stretch next to her. She proceeds through a basic core/stretching routine which I use as my in:

Me: "Hey I have a favor to ask. Take me through your routine quickly...I usually notice that girls are doing stuff that makes more sense overall. A lot of guys are just lifting as much as they can."

Her: "It's just a really basic routine; nothing special."

Me: "Ok, fine, hey let me try that," after she finishes rotating a medicine ball side to side. I'm probably pissing her off since she's in the middle of her routine and has a no-nonsense demeanor. "I actually do that on the decline bench."

Her: "Oh, is it harder that way?" She passes the ball to me and turns to doing push-ups on her knees.

Me: "Maybe. Try doing push-ups with this." I pass her a bosu ball, which she promtly declines.

Her: "Not today, thanks. Nice meeting you." She's gone before I can say bye.

I'm a bit disappointed, mainly because I like this girl more than the last 30 girls I've talked to. Oh well, I'll still ask her to go on a run with me next time I see her. Even though it felt like she wasn't feeling me I might as well get shot down outright before I give up.

It's a beautiful night. No excuses -- time for that long run outside.

Room for Improvement

Today was a valuable pick-up art learning experience on a couple of fundamental levels.

I took a quick lunch, and ventured out to CVS to buy a loaf of bread. Immediately upon exiting the building, I started looking to satisfy the daily minimum. Thanks to the lovely women of Boston, it wasn't hard.

The first "potential" I laid eyes on was in front of me in line at CVS. Unfortunately for me (probably fortunate for her), there was a 6'4" finance-type wedged between us, and I'm not at the stage of the game where my confidence is such that I'll put my dignity on the line without an escape route and so many onlookers. So, she was off on the horizon by the time I'd made my purchase.

It was about then that I realized I don't have a phone (lost it last week), and so my ability to end an approach well was severely crippled. No matter, either I'm in this for keeps or not. The question had become, who was going to make me the weakest link today.

Pretty soon, I saw a cute blond speed walking my way through the lunchtime rush. Since I was on the other side of a cross walk from her, I had a moment to compose myself and commit. I'm going in. I loitered as she crossed the street, trying to look like I was figuring what direction to go, and as she passed I said:

"Excuse me. Can I talk to you for a second."

Me: "Do you read blogs?"

Her: [looking dumbfounded ... and you are???] "Sure. Sometimes."

Me: "Are you in a rush? I mean, do you have someplace to be?"

Her: "I'm going home to walk my dog, but not really."

Me: "So you can talk for a minute?"

Her: "Sure."

Me: "Right. So a buddy and I started a blog. We're each supposed to talk to one stranger, a woman [wow ... that sounded ackward], a day who catches our eye."

Her: [recognition dawning ... looking around for cameras and maybe the police] "Heh ... uh ... oh, that's really nice of you."

Me: "Because, we figure people are so up-tight in Boston or in a rush to get home an walk their dogs, and this is a good way to meet women. So, you're the most attractive girl I've seen out during my lunch, and I wanted to tell you."

Her: [smiling ... she brushes my arm a little with her hand and turns to go] "Ohhh. That's really sweet of you."

Me: [spaced] "See you." [creepy thing to say, Captain ... yikes, but I'm still alive]

So, lesson #1: Cute from afar might still be cute up close, but she wasn't my type, I don't think. It's important to close the distance before going in.

Lesson #2: Unless you plan on asking to write her # down, like in the olden days, it's best to have a phone so that you're not just some creepy perv with a blog---you're a creepy perv with a blog and a phone who deserves a good shoot-down.

Lesson #3: Try not to sound like you're selling something ... say, a blog, for example. The Spare Change Newspaper guy probably has a better "in".

Alright, all's quiet on this front ... turning it over to Smooth.

Everyone's a Critic

Before I make an entry of today's events, I think it's worth discussing whether, in principle, by airing a private conversation---that I initiate---in a public forum (this blog) I destroy any claims to chivalry that Smooth and I set out in the introduction. I think not (naturally). Here's why:

First: I can't overstate our committment to approaching the women we think are attractive with the utmost respect. Slinging an untoward remark or obstructing any young woman's way about town is not an acceptable outcome. This should go without saying. However, what I've discovered in describing Game: On Boston to some of my closest female friends and aquaintances is mixed opinion ... and, so far, drastically so; some think that this is a great idea, that men need to be bold, and that seat-of-your-pants romance should come in vogue. I, of course, side with this camp.

On the other hand, some have expressed dismay that we're doing this; the criticism, this far, amounts to: "I'd be offended if you blogged about a private conversation we had on the street, and if I found out subsequently that we met because of this blog, I'd be upset." It's a reaction that I don't understand.

This brings me to my second reason for disagreeing with the disgust, for lack of a better term: any of these women we approach is free to shoot us down. Hard. And more power to them; they obviously aren't for us if they aren't the type that thinks this is a) mildly amusing, b) brave, c) flattering, or d) productive. I like to think that we are performing a two-fold service: we're making the pool of eligible bachelors for these women smaller by disqualifying ourselves, and we're giving other guys who read this blog case studies to improve their approach---whether it be imitation of avoidance.

Third: I know many of the women my age love reality TV. Nothing wrong with that, I cried for Jillian too. But ... don't you think it's just a tad hypocritical to indulge the voyeur in you despite the havoc the attention might wreck on the reality stars' lives. To the rejoinder: "They sign up for those shows and that life", I say "Yes and No." Do you think, had Jon and Kate known what trouble the media spotlight would turn out to be, that they'd have gone through with filming? Michael Jackson? And even if they would "do it all over again, unchanged", I don't agree that someone who agrees to talk to a stranger in public has any reasonable expectation that her conversation will remain private. Identities are protected (no pictures will be taken), and only if she reads this would she ever know to whom we refer.

Fourth (and in my opinion, most important): ladies, you can't have it both ways---either you want to be swept off of your feet or you don't. By forcing ourselves to get out of our comfort zone, we're increasing your odds of that happening dramatically (even more so if this catches on).

Long-short: I apologize to everyone who's offended by this adventure, but I think you're taking it a little too seriously. The woman who'd fall in love with me will see this for what it is: all in good fun.

Now, on to the main event...

Smooth gets punked -- big time

[Note: this post is totally off-topic since it has nothing to do with the Ground Rules laid out below. I decided to post because this little tale is pretty funny (at least I find it funny!)]

I took a girl on a few dates two years ago. Met her on Match. Dropped her when I decided she was mildly crazy since I had just gotten out of a relationship with a seriously crazy girl and it didn't end well (how could it have?).

Fast forward to tonight. Another Match date: I decide to meet a girl who looks very familiar at the bar at the Cheesecake Factory for a drink at 9pm. I'm sitting at the bar, when right on time, three girls walk in. It's her alright, just like I thought, with two friends. They grab seats down the bar from me, and proceed to completely ignore me. My girl is swearing her head off. She talking disparagingly about the Mandarin Oriental and some Mexican -- I can't make out much more. I distinctly recall her potty mouth now. Very classy (note: sarcasm).

I've been punked hard and sit there contemplating a move while they order food and drinks. I'm in no rush to handle this. To a certain extent I deserve it so maybe I'll marinate in it for a little while. I wait for 10 minutes and when their sushi shows up proceed to walk over. My girl is in the middle.

Me: "Can I get a hug at least?" I give her a half-hug as she swivels on her bar stool and faces me.

Her: "Whatever. Just don't touch my boobs. Someone's definitely not getting laid tonight. What do you fucking want?"

Me: "Look, I owe you an apology. I'm sorry. It was two years ago." [Lame but couldn't think of anything else]

Her: "This is my sister. Hey sis, meet douche guy here."

Me: "OK, have a great night ladies." I give her another hug goodbye and head out for a nice walk home across the Longfellow Bridge.

She texts me as I'm crossing the bridge. Here's the verbatim transcript of our texts for the next 15 minutes:

Me: I deserved that. I'll give you that much.
Her: Relax. You should have stayed. You are so much fun!
Me: Sarcasm? I can't even tell.
Her: I'm serious. Come back.
Me: I've always loved you. You know that. I've missed you these past 2 years. Please give me one last chance. [Personal confession: I'm somewhat mildly off-center too. Maybe I'm not that different from her]
Her: You're right. Your tenacity is attractive. So is your choking.
Me: I'll take that as a compliment.
Her: Nice. We miss you. You should come back.

Yeah, I got punked and maybe I kind of knew I was walking into a trap in the back of my head. But I did it anyway.

I've got game.

~11:45 pm, July 4th, Secession Day:

I was at the Beacon Hill Pub, with Smooth.  We were commiserating over beers, and a nice, cute young Beacon Hill-type asked politely if she could use the bar stool free on the other side of the table.  Naturally, I said "Sure; you can have the bar stool if I can get your phone number.  I don't have my phone (I've lost it, sorry ladies), but I can write it down for you."

She smiled wide and told me (twice, because I couldn't hear her the first time), "You've got a lot of game."  Then, about two minutes later, she winked at me from the next table over.  I'm pretty sure she was with her boy-friend.  

Not a bad way to kick this off ... not bad at all (brushes dirt off shoulders and pops collar). Sadly, I'm afraid this will be the last time I receive that compliment for some time.

Oh, and I've resolved to take pictures with the women I meet.  Hold on tight!  This could get ugly.

Who goes to the gym on the 4th of July? I do.

11:30am. I'm at the gym. It's empty. I've actually been semi-stalking a girl here but haven't seen her in a while and she's not here now. The upside is that in looking for her I've been working out religiously pretty much everyday.

I decide to break the ice on this blog and talk to the only relatively attractive girl in the gym. She's doing some kind of cardio/weights routine where she runs back and forth between the elliptical machine and the free weight rack. She's also wearing headphones so I'll have to be direct (and a bit rude I suppose).

Me: [as she walks over to the weight rack] "So what kind of hardcore training routine are you doing? I've never seen anyone go back and forth like that..."

Hard-core girl: "What?" She turns down the volume and takes her head-phones off.

Me: Back to square one and stupidly repeat my question. Not so smooth.

Her: "Oh it's this great routine my nutritionist game me. The point is [blah, blah, blah]"

Me: "Great, what's your name?"

Her: "My name is ____"

I realize at this point that she's nice and all but she's not quite what I'm looking for. I politely say nice to meet you and walk off.

I'm heading off to a couple of 4th of July parties. I got a good workout in; nice way to start the day.

Ground Rules

A few ground rules:

1. Talk to a girl a day or the poison will stay.
2. No cop-outs. That phone call with your mom or hello to a co-worker in the hall won't cut it.
3. She doesn't have to be a dime, but you gotta have at least a mild heart flutter or you're not breaking new ground (which is the point, dummy).

Get ready to walk, talk, and strike out around the block. Embrace it.

[To sum up:
1. polite, casual conversation with one (or more) single(s) a day.
2. effort must be sincere
3. no cop-outs/apologies ... must pursue wherever conversation leads; the goal should be a date, assuming she's not an axe-murderer
4. she doesn't have to be a 10, but she must distract your attention]

Off to the races

Well, ladies and gents (hopefully ladies, mostly). Let the game(s) begin. Click on my name (Captain) to understand what in God's name I'm referring to.

An epic adventure is begun, and these posts won't stop until my bride-to-be deactivates this account. If you play your cards right, that could be you!

-Captain