back to the Black Table

Union Street Grill is the archetypical meeting place for the new Boston working class: the mid-level account executives and java programmers who've replaced the plant foremen and dock managers as the city's economic hoi polloi. The former boiler house's exposed brick, stained maple trim, and flat screen TVs dispense a comfort-food aura on par with any Applebee's although, to its credit, the Grill was here when the word "franchise" still implied the vote.

I press through the swinging doors to the bar with a weird mix of high-school anticipation and "the-fix-is-in" confidence and stand behind the patrons on the stools. In front of me is a shoulder-length brunette set forward on the edge of her seat to reach her beer - slim figure, tight sweater, denim-clad hips - the only one of her demographic at the bar. I order behind her hoping my voice will make her turn, but it does not. The bartender slides my drink across, takes my cash, and I step back.

This is where it will happen; this is where I'll know. I linger for a moment, sipping, wondering, then I tap her shoulder: "Lisa?"

She turns… not exactly like her JPEG, but… better in a different way; remarkable. Certainly remarkable.

And I think, "This is gonna be okay. This is definitely okay."

It's on.

I went on the first of my two career-total Internet dates in winter, 1998. Things were different. Only 30 million savvy Americans were surfing the Web then (versus 165 million today), and not many were doing so for leisure. The Web was bold, its corners less traveled.

I was working as an analyst for one of the market research firms that fueled the "irrational exuberance." I sold a private "thought leadership" newsletter to a single client, the European Union. As a gig, it was mint: 12 pages each month on the trends, customs, and protocols of U.S. Web users. No hard data, just commentary on the issues. The online personals -- or Internet dating -- were an easy target. The story wrote itself before it happened. I could envision the executive summary's closer before I even turned on my PC:

"Americans aren't afraid to enhance their personal lives with technology. An adventuresome and growing community exists. But it likely will be generations before the science fiction of truly virtual romance can be a reality in a visual and material culture."

Internet dating was different then too. The notions of JPEGs and detailed profiles were in their infancy. The service I investigated for the newsletter read like a digitized version of the newspaper classifieds: two brief lines with age, status/race/gender, location, and a seven- or eight-word quote. Scrolling through messages, it took me almost a page to find an F in the gender slot.

In spite of (or perhaps because of) the crude interface, the whole concept invoked a sense of lottery. I was in my mid-twenties. I was on the company dime. I had nothing to lose. Yet even armed with insouciance, I neglected to tell anyone the premise for my project. Peter Steiner's famous cartoon, "On the Internet, nobody knows you're a dog" epitomized the Web-related moral majority.

In her profile, she was 22 -- a transplanted southern belle at a software company in the Metrowest suburbs; she was 5'8" and blond. I was intrigued and optimistic -- imagining a Dixie-land designer taking her shot in Silicon Valley East. We met at a Chili's or Ruby Tuesday's or the like, in a town home to no one I knew.

In reality, she was a super-sized 5'8" and not exactly a designer. She worked the phones and the front door at a start-up after quitting school for her military boyfriend. "It's funny how you end up where you end up," she said. From the time her eyes met mine, they said she realized this was going nowhere. She ordered a lot of food and ate it - and I was happy she did. "Eventually I'll get back to 'Bama," she said, "but I couldn't bear to go back now. I just wouldn't feel right with people." She was gracious when I grabbed the check, and she asked the requisite, "Want me to give you a call?" When I mumbled my excuses her disappointment was not marked with shock -- more like predestination.

I drove back to my office to write the story, feeling shallow and, in a way, perturbed that the moral majority was right; the stereotype held true.

Mack the Knife.

Things have improved. I think. In 2002, Americans spent $300M on Internet dating services according to the Online Publishers Association. Run the math, and that means anywhere between 3 million and 12 million people hung out their emotional shingle last year. Put more bluntly: if you're between 20 and 34 years old, and you don't know anyone with an online personals account - well, you probably don't know your friends. Internet dating is not only condoned, it's the real new, new thing.

An old roommate of mine, Mack, began extolling the virtues of Internet dating last fall. He's a good-looking guy, a securities analyst, a standout Division I athlete back in college. He frequents private parties and charity events. He's also the epitome of alpha male. He likes control; he likes a challenge, and he likes to win. The online personals became his new proving ground.

It didn't take Mack long to build a system of templates to create "personalized" introductory and follow-up letters that he can send to women on an online dating service at a rate of 15-20 an hour . Likewise, he can model the responses that come back by race, religion, location and other criteria to determine who would be an emotional match and who would be an easy lay. He's added a height-weight ratio to counterbalance misleading JPEGs.

He justifies his system. "You're competing with probably a dozen guys for each girl," he told me. "Like anything in business, it's a numbers game. You make a certain number of cold calls, and some percentage of those calls turn into sales. Some smaller percentage of those sales turn into the type of customer you build a lasting relationship with."

For Mack, it's a game to be won or lost. It requires training and strategy. "When I first started, I needed to improve my writing… to be witty and pithy. It was essential for winning the attentions of girls who get dozens of e-mails from other guys. Strangely, it's transferred into my real life. I can bang out a research brief much faster and as a more entertaining read than I could before I started Internet dating."

Back in the fall, Mack implored me, "With your writing skills and your wealth of pop trivia, you'd be a natural. You're single; get in the game."

But something wouldn't let me pull the trigger.


Not too many weeks later, a high school friend called me from New York. He'd met someone. She was perfect. He fired off an e-mail with some pictures; said he met her in the grocery store. I was amazed. The girl was more than kind of cute; she was striking. I wanted to hear more. In my entire dating life I hadn't met anyone in the grocery store. Then his story started to break down; the details didn't gel. He buckled under the questioning, the truth spilling out like trade secrets after the fourth margarita.

"How long have you been into this?" I asked.

"With this girl, or in general?"

"In general."

"I don't know. Maybe six months -- maybe a little longer."

In less than one year, one of my closest friends had met a dozen women via the Web -- live and in person (many for one night only). He'd chatted with double that and never followed through. He had serious ambitions for the girl he was dating now. No one in our crew had any idea, and only at this point was he ready to go public.

Maybe Mack was right. I struggled with my existing impression of Internet dating. I saw pictures or met women my friends were dating. The curiosity finally overwhelmed me. The sense of lottery was still there, as was another feeling that would take me a while to identify…

After New Year's I logged onto a personals service, created a profile, posted a pic, and tossed in the ante for a subscription.

As part of any online profile, you've gotta produce your "goods." Every service demands enough identifying data to present you to a prospect with more than a modicum of accuracy, and if you want some play, you'd better post a JPEG. My goods are as follows:


Blond hair/blue eyes

32 years old

Hobbies = running, indie music, snowboarding, lots of reading, and darts

I'll never replace Brad Pitt on People's most beautiful list, but I've never been at a loss for female companionship either. I'm not shy. I am more than comfortable stepping up to the plate in the flesh.


As I benchmarked my goods against the cyber suitors with whom I thought I'd be contending, I came to a realization. Aside from the simple curiosity and the gamble, the feeling that ultimately renewed my interest in Internet dating was of a grander scale: unadulterated romanticism. Because although I look good on the proverbial paper, a given truth remains: with all the women I'd met and the myriad relationships I'd entered and exited during my 20s, I had never found one where the bond could not be broken -- through a flaw of hers, or mine, or us both. Maybe, after five years of refinement and growing cultural acceptance, the Internet was the medium through which I would overcome the inevitable processes of elimination.

When meeting a girl in a bar or at a party, the process starts with the attraction; it ends with the fatal flaw of personality. But the Internet could flip the scenario: unveil the woman who wouldn't drive me crazy, and then make the equation binary -- we'd have an attraction or we wouldn't.

I stepped in tentatively, refusing to post my profile or JPEG publicly. I wanted to hunt, not be hunted -- and more honestly, I couldn't completely release the stigma from the supposedly defunct Web moral majority. I took Mack's assessment of my writing and my interests to heart. I sent out a handful of messages to only the most attractive women on the service. In a few cases I spent the better part of an hour crafting an undeniable proposition. I never doubted my success. I waited for the replies.

One thing hasn't changed since 1998. Women are the market makers in the online personals. Most receive 20 e-mails a day. A lot men will get more reaction from placing paper notes in bottles and heaving them into the sea. Suddenly Mack's mass-mail madness had some merit.

I received one response to my queries… and the ensuing e-mail thread quickly died on the vine. Apparently a digital Don Juan, I was not.

I hit my frustration and boredom levels in short order. Total messages sent: 5 or 6. Total days invested: about 14. I couldn't bring myself to daisy-cutter the database with templates and form letters to women I would never date more than once (if at all) - and even then only numbed by a six-pack. I made no conscious decision to quit; after two weeks, I gradually gave up logging in. The unofficial analysis: Internet dating was improving, but still not ready for primetime; like many other activities, old-fashion ways were still more efficient than the digital ones.


What's making the Internet dating industry the Web's real new, new thing is not only the amusement and, arguably, valuable service it provides; it's an uncanny marketing savvy. Months have passed since my hasty disenchantment with Internet dating. It's now summer, and I decide to terminate my service. When I log in to remove any trace of my digital existence, I am greeted by a handful of newly added prospects. The gimmick works…

Her goods:


Brown hair/green eyes

27 years old

Hobbies = running, music, soccer, darts

The darts snare me. The running and music, although a match, are fairly de rigueur in most hobbies lists online - but a woman who plays darts is original. Her JPEG - tall and rakish, standing in front of a dart board with a sexy blond friend - doesn't hurt her promotional effort. Her personal essay, while not exceedingly clever, is just vague enough to be intriguing.

I almost hit "reply" but I think better of it. I happen to be at my office, with no time to begin a flirt session. Then I think again: A) This girl is not going to respond to my reply, and B) I don't get any money back for the subscription I bought 5 months ago. It's that 1998 feeling of nothing to lose.

I do it: a three- or four-liner, frankly not all that entertaining, challenging her to a dart game. I log off. If she's interested I'll get an e-mail. Nothing turns up for a while, and I forget about it. I go on about my business at the office and preparing for my weekend.

It's Sunday. I have a lady friend in town for the weekend - a real-time example of another relationship that started with some promise and is eroding before my very eyes because of differences of opinion and dwindling attraction. As she showers I sneak downstairs to check my e-mail. Tucked among the spam is an automated response from the online personals service: User #LM75 has sent you a message. I click the link to view it.

Her name is Lisa. Her reply is succinct, playing heavily on our common interest in running. Her last sentence is an invitation to e-mail her at her personal address, one of the subtle ways an online player extends a branch of trust. Later that afternoon I sit down to address her.


For the next few weeks, we trade messages about three times a day. It starts as small talk, but really it's careful personal investigation. We talk about our collegiate sports experiences; we talk about music; we talk about grad school, which she is nearly finished with, and teaching - the gig that pays her bills. She writes well; she challenges me; she has a strong command of sarcasm. Our similarities begin to surface. Her parents have retired in upstate New York, about 15 miles from where I grew up and where my family still lives. She's moving across town to my neighborhood in Boston. She likes reruns of Miami Vice.

I ask her out. She declines. Too soon. She's still testing me for potential psychoses. I'm not dissuaded; the e-mail banter is enjoyable enough, and frankly I'm not interested in pushing it. Why spoil the sense of romanticism that increases like inebriation -- each exchange another drink in the bloodstream? Anyway, I'm leaving that night to spend the weekend with friends at the beach.

We pick up the thread when I return. The first half of the week is a flurry of barbs, sarcasm and more small talk. We spend one evening trading Top-5 lists until well past midnight. She confides to me some of the weird e-mails she's been getting from other guys replying to her ad, making particular light of a guy who itemizes his house in the Hamptons and his box seats at Fenway. She names him Pravda Boy (after an overrated night club in town).

On Thursday she pulls the reversal:

"So when are you going to ask me out? I'm beginning to think you're playing hard to get…"

"I tried this path once already, remember?" I reply. "Why don't you ask me?"

"I'm bad at making decisions," she answers. "Now you're giving me the first-date jitters already."

I ignore this just to string it along. Over the next several days we debate about the upcoming date. Lisa starts asking more serious questions, whether I have any drug habits or other skeletons to expose. I don't, and I'm back to the beach house for the weekend, so our thread is going on hold. We set Wednesday night as the time for our meeting.

I return home Sunday night to find several messages from my -- my what? What is Lisa in the taxonomy of acquaintances, lovers and the spectrum in between? The first is a multi-page confession of her planned Friday night. She actually had scheduled a date with Pravda Boy; he stood her up. At midnight she was home alone e-mailing me with tales of a traumatic recent breakup and general self loathing. Not long after midnight she e-mails me again to apologize for whining. Immediately after, she writes again to apologize for acting like Mikey in Swingers -- contacting me over and over without response. She gently requests that I agree not to meet anyone else before our date on Wednesday.

From any woman I have dated in the past half decade, this behavior would annoy me or scare me or both, but as I sit at my desk on Sunday night I feel… relieved. I start thinking about things like the convenience of holidays and the proximity of our parents.

I reply to allay her concerns and to give her a ration of shit for considering a date with another guy. We laugh it off. At some point she broaches a topic we have suspiciously avoided: What if we meet and it doesn't work? What happens to this daily chatter that we've both come to rely on?

I'm sure things will work out. In three weeks, I've seen no warning sign. But my mind starts wandering… 5'8"/135, is that big for a girl? I look at the JPEG again. She looks great, but the photo is kind of dark. There has to be a catch. And I have my own problems. In a stupor during the weekend, I burned the skin off my lip on some late-night pizza at the shore. What will it look like by Wednesday? Maybe not good.

On Tuesday I propose canceling. She can go either way.


Wednesday morning things are fine. I e-mail, tell her we should go for it; I'll meet her at Union St. at 8:30. I leave my cell number if she has any problems. When she calls in the afternoon to confirm, it's the first time I ever hear her voice. Pressing "end" I contemplate the problems. Maybe she used a phony picture; maybe she can write, but she won't be able to talk. For the first time in seven years I am hoping for something to work out.

Her picture portrayed a very cosmopolitan figure, but the woman in front of me looks innocent, almost girlish. This does not diminish her attractiveness, her enticing physique. We stare at each other for a moment, neither betraying any emotion. What do we do now? Shake hands? Hug? We've known each other for weeks, and it seems longer, but… We shake hands and head upstairs to the dart board.

Our conversation consists of sentence fragments, continuing topics we started during e-mail exchanges long before. The dart board is occupied, so we play pool. We're so competitive during the game we barely speak. She wins. (I'm legitimately shocked; I play a lot of pool...) I order another round of beer, and the dart board frees up.

We pair up with another couple -- teachers -- and Lisa makes effortless conversation with them. The game ends, and again we're alone… and out of nowhere I feel it happen. I hadn't picked up on it during the games, but… somehow I'm blowing this. We aren't making eye contact. I run a test: I offer to get another round and brush her arm as I make for the bar. She recoils as if bitten. When I return, I offer to grab a table, to just sit and chill. She'd rather play more pool. I almost protest, think better of it, and we play.

"I think I've gotta get going," she announces when the game ends. "I'd like to hit a video store to pick something up for class tomorrow."

I really have nothing to say to this. I'm still in disbelief, tongue tied like a rookie.

We're outside her car. She turns to climb in without a good-bye -- her actions rushed.

"Hey," I interrupt her. She stops, turns to face me. We're standing six feet apart.

"Hey what?"

"Well, what do you think?" I already know what she thinks. I've played her part too many times -- but I ask anyway.

She stares blankly. No reply.

"I wish I wasn't this old," I say under my breath barely realizing it slips out.

"Old?" she asks.

"Nothing; I didn't mean what you think... So, do you wanna do this again? Are you just not diggin' me? Doesn't matter either way, but I'd like to know."

"Do what?"

"I dunno, this… go out?"

She pauses. "Why don't you e-mail me tomorrow?"

"Sure. But that's not going to change the question."

"Just e-mail me tomorrow."

I send the e-mail first thing in the morning. The question doesn't change. Toward the end of the day I get her response:

Thanks for the darts and pool last night... As for "not diggin' you," that's not it at all. I think I'm just not ready to start seeing people yet. My boyfriend and I broke up at the end of April after two years together. And we were living together when it ended. It's been tough, and I'm beginning to realize that I need to spend a little time on my own for a while.

Anyway, I definitely enjoyed e-mailing with you. You're an awesome writer... made me laugh a lot. Best of luck.

It's a bull shit send off, spurious, but even before I got her response, I had been taking stock. I've had a long career. I've dated prettier women, had deeper and more complicated relationships. But after this I feel hollow, unfamiliar, as if the world has moved in reverse. And it has. The Internet worked; I just didn't wind up winning.

I try and put this ethereal and ephemeral interaction in its proper context. By real-world terms, it is nothing, but the weeks preceding the meeting distort the magnitude of the event. And there's the sudden lack of honesty that stains her final message. I don't truly feel jilted; it's more… lost opportunity.

I guess if we've learned anything since 1998, we've learned the Internet can do that.