My Week with David Rakoff

David Rakoff

Much like David Rakoff’s starry fantasy of befriending Bette Midler on a film set, returning to “her rambling apartment.  It will be the maid’s night off and we’ll eat leftovers from the icebox: cold chicken and pie.  Milk from a glass bottle….” (“The Satisfying Crunch of Dreams Underfoot,” Half Empty), I harbored a similar fancy last summer.

I had applied for and in April been accepted into the Stony Brook Southampton Writers Conference, a week wherein aspiring authors and essayists are immersed in workshops and lectures given by esteemed literary faculty — Susan Cheever, Jules Feiffer, Mary Karr, Roger Rosenblatt, Meg Wolitzer … David Rakoff’s name popped out at me.  He was teaching a personal essay workshop for a week in July and while the cost was in the thousands, seven days with Rakoff would be heaven, I thought. 

Workshops were touted as smallish and intimate, so naturally, all of May and June my daydreams revolved around elaborate scenarios wherein on the first day of class, David took immediate note of my pithy comments and wry observations. Following his first class assignment — to write an essay about our earliest memory — David would scour the room, then point in my direction and ask me to read my piece out loud. Pleasantly surprised by my skill, he’d laugh heartily at my witty phrasings but would also nod in approval at the depth behind my cleverly chosen verbiage.

Then he’d pull me over after class and whisper, “What are you even doing here? This workshop is for amateurs!”

“I really just wanted to meet you,” I’d confess sheepishly.

Then we’d go to lunch on campus every day, but sit huddled together, just the two of us, sharing tunafish sandwiches while we exchanged gossip about David Sedaris and Ira Glass. Really he had all the gossip; I’d listen raptly, enthralled by his hilarious stories; stuff he’d never shared with his friends but knew instinctively that he could trust with me — only me.

After that week, because he was notoriously generous and kind, David Rakoff would offer to be my mentor and introduce me to his agent and editors, as his protegé.  We’d have weekly lunches at the Stork Club and I’d be the envy of every single nonfiction writer in New York City. And beyond.

But none of this was to take place.  And not only because it was a ludicrous flight of my imagination.  In early July of last summer, I received an email from Stony Brook stating that due to advanced illness, David Rakoff had to pull back from my workshop.   They found a substitute teacher.   I asked for a refund and scolded myself for entertaining pointless notions about us.

Still, I thought, as I unpacked my suitcase with a heavy heart, I had been this close to being in his presence…and that would have to suffice.

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