What are your earliest memories of Kingston?
I remember nursery school at the oasis of Hillel Academy; going to Cable Hut and the drive-in, and the bleakness of the 70s; garbage and political graffiti everywhere, neither puss nor dog on the street, the shots and helicopter searchlights at night, the empty shelves. And, the great music that was always there in the background, that era of very slow dub.
... And of Port Antonio?
My aunt had a very hip wedding on the lawns at Goblin Hill, with all her theatre friends in spectacular 70s finery; Dennis Scott was in a turquoise jumpsuit.
What has been your most memorable meal in Kingston?
A Colin Hylton-catered lunch at a Christmastime day party in Greenwich a couple of years ago was excellent, and a class act to boot. But any pan chicken I had outside of Seawitch was probably even more appreciated then.
What do you miss most when you are away from Kingston?
The late-afternoon views from Sunset Drive and from Mona dam.
What would you do if you were mayor (of Kingston) for a day?
Agitate for the amazing Port Royal redevelopment plan my father has drawn up, and his proposal to make a model streetscape out of a stretch of Tower Street. Have ferries, trees, lights, bike lanes, weekend street pedestrianisation, and solar panels everywhere.
Share the title of the last book you read
A Tenured Professor by John Kenneth Galbraith.
What is your middle name?
What was the last bit of music you listened to that you truly enjoyed?
We Used To Wait, by Arcade Fire.
What was your last bit of retail therapy?
About 15 songs on the iTunes Store I had been tagging on my phone with that app, Shazam, for months.
Share some places in your travel black book.
There's a small desert, with real, Saudi-ish sand dunes, at Mui Ne in Vietnam, where you can slide down the dunes on your stomach and, later, hike up a nearby gorge of thick, red mud. The intimate bar The Other Room in Greenwich Village, with its brick walls barely lit by candlelight, is a pretty unparalleled date spot. Istanbul makes you feel like you're in a Sean Connery Bond film. And Reach Falls, near the St Thomas border, is stunning.
What cologne are you splashing?
You are perhaps best known as a former writer for Vanity Fair. How long were you there and what was that experience like?
I was actually very low on the totem pole as an assistant to one of the editors, though writing was certainly part of my job. I was there five years and, pay aside, it was an amazing experience. I met bright, funny people, and you got to meet boldfaced names you'd always heard about, and feel that you were in a small way at the centre of a certain kind of glamorous scene in New York. It opened all kinds of doors, and in those days, the company was very good with the perks.
You are currently writing a feature for Ocean Drive magazine. Are you back into writing?
No, not full-time. The editor of the magazine is a friend of mine and she occasionally brings me out of retirement to do a piece, on the side.
What else are you doing?
Researching my next job while helping two friends raise money for their funds, and two others with their expanding companies.
What are your New Year resolutions?
Lots more forward motion, in every way.
Who is your literary crush?
Content-wise: Naipaul, Chekhov, Greene, Conrad, Marquez. Attractiveness-wise: Kelly Oxford and Nicole Krauss.
When was the last time you had a really good laugh?
This summer at a play called One Man, Two Guv'nors in New York, an update of a 1740s Italian comedy. I was embarassed; it was uncontrollable.
... And cry?
Long ago: I think after I saw Schindler's List and just walked out onto the quiet street and cried, thinking the most basic, child's thought, directed at the Nazis: why did you have to do that? It's a shame it's been that long. Crying is cathartic.
Finally, what's your philosophy?
Dress British, think Yiddish.