1

In the fall of 2005, two months after moving to New York, I was asked to moderate a panel with David Rakoff at the Texas Book Festival. His second collection of essays, “Don’t Get Too Comfortable,” had just come out.

I admired David’s work on “This American Life” and his first book, “Fraud.” I wanted to be friends with him. Or, at the very least, to avoid looking like an asshole in his presence. One afternoon, I typed up an introductory email of flattery and self-effacement. I asked him to lunch after our panel. His response came hurtling back 30 seconds later. Although the email has been lost to time, I can still remember its particulars: Lovely to meet you, first time in Texas, won’t be able to have lunch, which is a shame. I’m a Jew who loves pork.

I was thunderstruck. How could someone so important email so fast?

That October, when I introduced David at the festival, I made a small joke of this. The final lines of my introduction went something like, “David Rakoff is an exquisite writer. He is a careful observer and a genuine wit. He is also the fastest emailer I have ever met.”

David walked to the microphone and smiled at me. In his marvelously modulated baritone, he said something like, “It’s a curious compliment to be told you are a fast emailer. Because the truth is that you are just staring at your inbox … waiting. Waiting. Waiting.”

He drummed his fingers on the podium each time he repeated the word. It was a delightful bit of theater. I have known many clever writers. But I’m not sure I have ever known a clever writer as comfortable on stage as David Rakoff.

2

A few months later, I went to dinner with David and my friend Clay, who runs the Texas Book Festival. We went to some Nobu off-shoot in Tribeca: Nobu Lite, Nobu Snack, Nobu After-Dark. I was still new to the city, still hoarding fancy experiences to brag about to friends back home, and this was a humdinger. I also wanted to impress David, which probably insured that I would not. I drank fast. I made lots of jokes, some of which made no sense. Young writers are envious and greedy and insecure (old writers can be, too), and David brought out all three in me.

“I mean, how does anyone write a book?” I asked at one point.

“I have no idea,” he said, his eyes going wide. I thought he was being clever again, but he was not. His books were collections of essays he’d written for magazines and radio. This is something agents and publishers will warn any aspiring writer against doing. Collected essays don’t sell, they say. Unless you’re one of the Davids.

So he had a privileged career, and it meant that aspiring types wanted to be close to him and rub a little of his magic onto themselves. Seven years later, I understand this is an odd position, because there is no answer for how to get his career, and like all writers and neurotics, he was probably just worried about how to keep his career. Writers come rushing into battle all around you, wielding their broadswords and asking for instructions, and it’s like: Oh, god, you too? I’m trying to kill a motherfucker right now.

If my questions and my ambitions bothered him, though, he never showed it. In print, he could be hilariously cutting. But he was kind to me that night, and every time I saw him since.

“Has anyone ever told you that you look like Amy Adams?” he asked me at one point. I was not yet familiar with the actress who starred in “Junebug” and would go on to become a Hollywood star. I shook my head with that slightly worried look, trying to measure what he saw in me, and he gave me the warmest, most reassuring smile. “It’s a good thing,” he said. “I promise.”

3

Years passed, and I did not become friends with David Rakoff. But he was always friendly to me. Part of my job at Salon was to reach out to marquee writers whose books I had cherished, and I would send them strange requests with trembling hands. He still wrote back fast.

“Howdy, ma’am!” his responses would begin. “Howdy, mister!” I would write back.

He was sick with cancer again, in and out of treatment, which made the responses that much more gracious. He was usually writing to decline. (We did get him twice in Salon during my tenure, although both pieces were with other editors: A brilliant review of “Bruno,” and a tender essay about an obsession with painting eggs.) But maybe it felt good to know he was still wanted, because writers have a terror of the love just disappearing, maybe even more so when they are being pushed around on cold metal gurneys and suffering the flimsy indignity of a hospital gown.

I don’t blame any writer who ignored those strange requests from me. When you achieve a certain level of fame, hands tug at you from all sides, and it’s hard to find creative ways to say no. But when someone you look up to takes the time to meet your gaze, thank you for asking, and give your hand a squeeze, you don’t forget it. Nick Hornby did this once. But David did it always.

4

When I quit drinking, and I no longer knew how to talk to people, I would take long walks through the city and listen to podcasts. Other people talking. It made me feel like I had company, and I would lose hours this way. One afternoon, I walked to Grand Central Station and took myself to dinner at the Pearl Oyster Bar, as resplendent a New York experience as one can have. So many people coming and going. It just steals away all your loneliness.

On the way there, I listened to David’s interview with Terry Gross on “Fresh Air.” His third collection, “Half Empty,” had just been published, and it was an acerbic gem. There is a story in that collection, “Isn’t It Romantic?,” about the musical “Rent” (which he despised) and living in New York and trying to create art, and I read it during a dire creative period, and I remember thinking: Well, that’s as good an essay as anyone’s going to write. Might as well hang it up. But his work was inspirational, too. You saw that he struggled: “Writing always only starts out as shit,” he writes in that essay, “an infant of monstrous aspect, bawling, ugly, terrible.”

An infant of monstrous aspect. I’d have to remember that.

I learned so much from David. When I read his work, when I heard him talk, I felt smarter and wittier and better. One of the other Davids – Foster Wallace – said that reading is like the Vulcan Mind Meld. “Their brain voice becomes your brain voice” (from “Although Of Course You End Up Becoming Yourself”). And having the Vulcan Mind Meld with David Rakoff gave life such crisp edges. Thoughts became sharper. Syllables had an extra kick.

There is one moment in that interview that sucker-punched me. Terry asks David to read a passage from the book. It is a chapter about terminating his relationship with his longtime therapist, who was upset by the decision and told him so.

Should you happen to be possessed of a certain verbal acuity coupled with a relentless, hair-trigger humor and surface cheer spackling over a chronic melancholia and loneliness – a  grotesquely caricatured version of your deepest Self which you trot out at the slightest provocation to endearing and glib comic effect, thus rendering you the kind of fellow who is beloved by all yet loved by none, all of it to distract, however fleetingly, from the cold and dead-faced truth that with each passing year you face the unavoidable certainty of a solitary future in which you will perish one day while vainly attempting the Heimlich maneuver on yourself over the back of a kitchen chair – then this confirmation that you have triumphed again and managed to gull yet another mark, except this time it was the one person you’d hoped might be immune to your ever-creakier, puddle-shallow, sideshow-barker variation on “adorable,” even though you’d been launching this campaign weekly with a single-minded concentration from day one … well, it conjures us feelings that are best described as mixed, to say the least.

It’s a majestic, tumbling sentence. “A lasagna of a sentence,” he says in the interview. But it is so, so dark. I’m not sure if it makes sense out of context here, but it’s just viciously self-aware and bungled up and tragic. And I swear that in the version I heard (which is not in the condensed version posted on NPR’s site recently), Terry Gross asked him about that one pinprick of phrase: Beloved by all yet loved by none.

She asked him something like, “Is that how you really think about yourself?”

And you could hear the hesitation in his voice. I couldn’t tell if the silence was irritation or embarrassment or sadness or resignation. But all I can remember him saying is: Well, yes.

5

The last time I saw David Rakoff alive was on Governor’s Island, a lovely little boat trip off the tip of Brooklyn. He was walking by himself, hands in pockets on a brisk spring day, and I was on a date with a nice guy I would gently reject in a few days, and I started to say something to David, but he looked so happy, walking in solitude.

No wait, the last time I saw David Rakoff alive was on the movie screen in the Northpark Theater, where my friend Allison and I had bought tickets to the film broadcast of “This American Life,” and David gave a performance so moving that all you can do is simply say: You should watch it.

Earlier this morning, as I was writing this, I did a search in my inbox for emails from David, hoping to quote from our correspondence, and I was surprised to find hundreds and hundreds of letters pop up. That is because I mention his name in an email that I send to all first-time contributors. It is a letter of gentle warning and encouragement meant to assuage the fear of people who are walking onto this battlefield for the first time. We forget, those of us who have been here for a while, how scary it can be: The mean commenters, the vulnerability of being yourself in a public forum. So I like to send that letter, and I like to mention other writers who have made this foray too, in the hope that it might make them feel a little bit prouder, a little bit safer. Just knowing that where they are headed, David Rakoff was there, too.