thinking of you

Read Strunk & White, Poynter or Zinsser, and you’ll emerge with at least one common tip for improving your writing: know your audience.

Which, for most documents, is undoubtedly good advice. Penning a Sunday Style article (seriously, Barbara, it’s almost finished), a business proposal or a birthday card, it helps immeasurably to keep the eventual reader firmly in mind.

With this blog, however, audience-focused writing is a much harder trick to pull off. Not solely because I have absolutely no idea who most of the thousand or two people who float through this site daily are, but also because the groups of people who I do know about are all looking for such divergent things.

Based on the posts that get linked on other blogs, or del.iciou.us bookmarked, it’s pretty clear s-a’s readership is composed of several, fairly distinct groups. There are the 43Folders-ites, thrilled by any mention of productivity hacks and Getting Things Done; there are the startup wonks, looking for entrepreneurial insights and tech business ruminations; there are the film folks, hoping to pitch Cyan (and now Long Tail) and looking first to unlock the secret that will get them cast or hired, or launch their screenplay into production; and then there are the large number of generalist voyeurs, the people hoping to live a bit of the disastrous New York dating life through my vicarious misadventures.

Since I know no single thing I write could make them all happy, I essentially don’t even try. I don’t balance out the flow of postings to make sure I cater regularly to each group, or even neatly section off one kind of writing from another. Instead, as they do in my brain, the thoughts all simply jumble up on the front page, intermixed, sometimes even within a single post.

But while I’m able to block from my mind (wisely or not) the varying groups of readers, I occasionally find myself writing to one single reader. I write, in short, knowing that I’m being blog-stalked by a potential date.

In my prior post, I said that I don’t seem to have a type, a regular pattern that emerges from my dating past. Which, in fact, is only partially true. When I last tallied my kissing count, I re-discovered something that I’ve long, at least subconsciously, known: I tend to like writers, especially those that self-reflect mercilessly, that pour their inner life onto paper (or screen). Which makes me, in short, remarkably good at developing crushes on fellow bloggers.

I say this all to preface admission of my own potential-date blog-stalking. In the world of business, I tend to obsessively research investors, clients and hires. Which has carried over to my personal life, where, especially in the case of other bloggers, I tend to follow along with new postings, to pore over bits of the archive, looking less for the what and more for the underlying why.

And, projecting perhaps, I tend to imagine that potential dates are doing the same thing. The contents of my archives are fairly immutable. But new postings – over that I have some control. So I tend to second guess my own ideas, question topics on which I might typically hold forth. I look at potential posts and wonder how they make me sound. Too dorky? Too neurotic? Too excited about the companies I’m trying to build?

Fortunately, I rarely pause long, as, in fact, I’m at least as dorky and neurotic and excited as my writing might imply. That’s just who I am. And while trying to hide that, even in the off chance that I could pull it off, might help me score a first, or even third, date, it certainly wouldn’t bring me to the the thiry-first or seventy-third.

Frankly, that’s a whole lot of work for a rather brief-lived payoff. So much of New York dating – the posing, the game-playing – it only works for that brief stretch when you have the interest and energy to put in the effort. Which is why, even during those stretches that I’m sure (rightly or wrongly) someone I’d really love to impress is reading along, I fall back on the same strategy for writing as I’ve gradually come to for real-world dates: stop trying so damn hard, stick to the truth, and hope for the best.

While, short-term, it’s probably not the most effective strategy (either for keeping readers or for getting laid), in the long run, it’s the only hope I’ve got.

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January 23, 2005

typifying

Though I may, through this site (or, plausibly, in real life) come off as an insensitive prick, in fact, one of the few things I do well is empathize.

I don’t mean empathize as a synonym for sympathize, as in sharing someone else’s pain, but rather empathize in its purest sense, as in divining what other people are thinking, seeing things from other’s perspectives.

Tailoring a sales pitch on the fly to an audience, or searching out the perfect birthday gift, I’m grateful for this knack of putting myself in other people’s heads. But, like most things in life, it cuts both ways. Given the weight I put on what other people are thinking, I inevitably end up worrying about what other people are thinking of me.

This manifests itself in small, bizarre ways. Hearing female friends mock the wall-eyed guy at the end of the bar, for example, I’ll start to convince myself that perhaps I, too, have some horrible lazy eye and yet have never been told as much, even though it’s been secretly discussed for decades by friends and family behind my back.

I can usually cast aside such fears with a moment of reflection. I’ve seen countless pictures and videos of myself, and I’m sure that in at least the majority of them both of my eyes are looking more or less in the same direction.

Which leaves me to fixate instead on the things I hear and deduce on a regular basis. Some of them (“has anyone ever told you that you look like Matthew Broderick?”) don’t imply much beyond their surface content (I apparently look kind of like Matthew Broderick). But others I can’t keep from analyzing, from tearing apart for their loaded meaning.

One I’ve heard a lot recently is, “I’d be really, really curious to see who you end up marrying.” I’ve gotten this one, even in just the last month, more times than I can count. I think what this actually means is, “you seem like a judgmental asshole with bizarre and inscrutable dating criteria that make it nearly impossible for me to figure out your ‘type'”.

I must give off this impression in spades, because if I comment on liking a girl I’ve just met, friends usually react with, “really? I thought you didn’t go for [taller / shorter / thinner / curvier / blonde / brunette / smart / dumb / etc.] girls.” As I don’t think I say such things directly, I’m curious as to which obliquely snide comments or quirky reactions lead people to those strong impressions. Whatever it is, it’s powerful stuff. When people make such comments, there’s almost an air of helpful reminding. “Actually,” they seem to say, “despite the comment you just made to the contrary, I’m pretty sure you don’t like her after all.”

Hearing this from enough people, I start to suspect they’re right. Maybe I don’t like smart girls. Or stupid girls. Or tall blondes or short brunettes. I have absolutely no idea. Looking back through the wreckage of relationships past, I can’t quite make sensible patterns emerge.

Which is exactly the point. Perhaps the reason people so quickly rule out possibilities for me is that I’m so slow to categorically rule them out myself. My dating life, taken together, is an enigmatic, jumbled mess. Not a clear shape, but a muddy splatter.

Which makes what people tell me I am (or, more frequently, am not) looking for far more interesting, gives me license to listen carefully to friends’ constructive critiques of my crushes. Not because it’s likely to yield clues in my own search, but rather because it might give me a glimpse into theirs. Given the spattered mess of my own love life past, I seem to have inadvertently become a walking relationship Rorschach blotch.

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January 21, 2005

pick me up

My friend Yoav is moving back to San Francisco tomorrow, so he and our mutual friend Colin met up for a last drink. As I stood outside the bar, waiting for them to arrive, an attractive young woman came over and started up a conversation.

A few minutes later, when Colin and Yoav arrived, Lina somehow invited herself to join us. And, when I left the bar, two or three pitchers shared between us all, I had lipstick on my collar and a phone number scrawled on my hand.

Which, frankly, struck me as more than a bit worrisome. Perhaps it’s a sign of living too long in New York, where distrust of strangers runs a close second to public urination as a grand tradition. Or perhaps it’s the the general effect of living in a society where guys are normally required to be the pursuers rather than the pursuees. Either way, as Colin’s girlfriend Carrie later pointed out, if someone came up to me on the street to offer a free pizza, I’d similarly be a bit hesitant about taking a first bite.

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January 3, 2005

an admission

Due to a recent conversation with visiting out-of-town friends, I sat down to make a list of all the girls I’d kissed in my life. And, while I was moderately disturbed by the vagueness of a fair number of listings (‘UCLA volleyball player at Devin’s beach barbecue – possibly named Sarah’), I was even more disturbed to discover the high percentage of bloggers on the list. With a bit of reflection, however, that made good sense – as long as I can recall, I’ve always instantly developed a crush on any girl who writes unusually well.

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October 24, 2004

time capsule

In the messenger bag I lost earlier this week, along with my phone and iPod, was a little leather Filofax book I use to jot down notes. Yesterday, looking for a temporary replacement, I pulled out an old bound journal from a year back that still had some blank pages left, and tossed it in another bag that was in my closet.

I headed out with the journal in tow last night, when I met up with Sarah Brown for drinks in Brooklyn. And, on the subway back, I started thumbing my way through, reading over the array of entries made by an earlier me.

One of the pages, about halfway through, was a list of quirks of the girl I was dating at the time – how she scrunched her nose when embarrassed, over-pronounced the word ‘literally’, placed a piece of ginger atop each piece of sushi, or shook her head slightly to free her ponytail each time it got caught up in the collar of her jacket.

Just a few days before, I had been thinking about that very girl, trying to remember why I was so desperately in love with her, why I had set out on a relationship that anybody could have said (and often did) was doomed from the start. And, as I made my way through the list of idiosyncrasies, thought back on how she looked down, embarrassed, when laughing too hard, how she closed just one eye when she needed to concentrate, it all made perfect sense.

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September 4, 2004

meeting up

As post-graduation celebration, my parents are now en route to Ischia, Italy, the site of their engagement some thirty-three years back.

And, certainly, engagements are important – particularly now, when “how did he do it?” supercedes even “can I see the ring?” But meeting stories, I’ve always felt, are what really count.

My grandparents, for example, met at a baseball game – my grandfather, who played catcher, had forgotten his lunch. My grandmother, a cheerleader for the other team, offered to share hers. With that beginning, how could they have weathered less than their seventy years of happy marriage?

My parents, on the other hand, ended up in Ischia in a more round-about way. Both were students at New York City’s Queens College. My mother ran the college newspaper, my father the radio station. He appeared on my mother’s doorstep two hours early for a joint media meeting being held at her house. He was on his way back from Jones Beach, wearing a tank top and short cutoffs. Depending on whose version you rely upon, he may also have had some nameless girl in tow.

My father, apparently, was instantly smitten. My mother, on the other hand, was instantly convinced my father was a jackass. Still, with a bit of persistence, he managed to drag her out on a date, and then another. He was serious. She continued to see other guys. But they dated, on-again, off-again, from that point.

Towards the end of their senior year (during, I believe, an ‘off’ rather than an ‘on’), my father asked my mother if she had any post-graduation plans. Actually, she did: having never traveled abroad, she was setting off for the summer to tour Europe and Israel. My father, with absolutely no summer plans, jumped on the chance: he was intending to do exactly the same thing – perhaps they could go together?

Somewhere in the extensive pre-trip planning, off became on, and when their flight left JFK, my father’s mother famously turned to my mother’s mother to ask if she had renewed her passport. Renewed her passport? Yes, just in case their children decided to hold the marriage abroad. After all, my father had decided that they were getting engaged, and he was particularly good at getting what he wanted.

And, in fact, he did get what he wanted – though the wedding wasn’t until the following fall, they sent back news of the engagement via telegram.

My brother and I, to this day, give my mother a hard time about their story. Growing up, nearly every pet we ever owned, we bought on the trip back from ski weekends up in Bear Valley. Take her out of her environment, we knew, and she’d come back with all kinds of housemates she’d never have agreed to back at home. My father, it seems, new exactly the same trick.

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July 26, 2004

signs of aging

Re: really hot girls with brains of toothpaste:

Now, once I know I could, I no longer have to.

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July 18, 2004

periodicity

A girl I recently started seeing (inevitably) discovered this site, and spent some time skimming through the archives. She emailed to say, “you appear to have various recurring patterns in your life in this order: sleeplessness, illness and the avid (drunken) pursuit of women.”

To which I can only respond: it is, indeed, a vicious cycle.

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May 4, 2004

helpful note

If you have a female caller on a weekend evening, and she finds a business card on your desk with a different female’s name and phone number scrawled on the back, she likely will not be terribly amused.

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April 26, 2004

glass slipper

Sunday evening, direct off the plane back from Denver, I headed to the Tribeca Grand, to screen I Love Your Work for Stellar Network, a young New York filmmakers networking group. After the screening (and a brief Q&A session), I headed up to the bar where a small group of attendees had congregated. Among them was a very attractive redhead, and I smoothly sidled over to strike up a conversation. Not just attractive, it turned out, but smart as well – a screenwriter who spent her days working at the Legal Aid Society. Before I had the chance to ask for her phone number, however, I was pulled away briefly by the event’s organizer, who wanted to thank me for screening the film. A few minutes later, when I turned back around, the redhead was gone.

Despite the Cinderella act, I realized there was at least some chance she’d be materializing again for Stellar’s monthly bar party, which happened to fall yesterday evening. I had a dinner meeting (with an OSU undergrad who also serves as publisher and CEO of the highly successful brass|MEDIA finance magazine – we wunderkinds try to stick together), and hoped to head down directly. Post-dinner, however, I realized I didn’t have the address on me, and so called a friend from Kentucky who works at Miramax and belongs to Stellar. Did she know where the party was? Absolutely, she drawled back; she was headed there herself, and she was fairly sure it was at some bar on 9th between Avenue A and Avenue B.

As my cab turned onto 9th, however, it hit me that, unless the party was a barbecue, the address she had given couldn’t possibly be correct; between A and B, 9th St becomes Tompkins Square Park. By that point, however my Miramax friend had apparently already ducked into the bar, as she was no longer picking up her phone. After dialing through the list of all the people I knew who might be at the event as well and wandering a bit through the surrounding blocks hoping I’d see someone I knew outside the correct bar, I finally gave up and stopped in at Doc Holliday’s for a drink.

As I was walking back to the subway to head home, I got a call from one of the other attendees I had tried to track down. On 9th between A and B? No, the bar was on 9th between 3rd and 4th. I hoofed it over a few blocks and headed in. By that point, however, the party was on its last legs, with everyone jacketing up to head home.

Still, a bit of detective work yielded that the girl had, in fact, shown up briefly earlier in the evening. Further asking around even turned up her name. So, armed with that, and the bits of biography recalled from our initial conversation, the Google search is on. Once again, blurring the fine line between charmingly determined suitor and crazy internet stalker guy.

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April 1, 2004