From Shirtsleeves to Shirtsleeves in Three Generations

Tuesday found Faux Hillary out of his league. Or not quite out my league, but certainly far away from my comfort zone (read Spadina and Lonsdale).

I found myself attending a function at the city's much vaunted Drake Hotel. The Drake is a bar, come hotel, come scene in and of itself. It's opening is credited with transforming a once wayward stretch of Queen Street into hipster central. The beautiful patio opening one summer when we were all watching the OC and everyone was adding the word "the" in front of everything, hence the obsiqutous, the Drake. Remember that summer; thank god that's over. For a summer everyone and their monther (except for Sim Sim Sima, she's has NO time for bars) was talking about how much of a genius Jeff (owner of the Drake) Stober was.

The Drake is one of those places that isn't actaully cool anymore (some may argue it was never 'cool' at all). The Hipsters have moved on from Queen and Ossington, further west, and wouldn't be caught dead inside of the Drake; regardless though there's enough of grit left on the streets surrounding for the city's I-Banker crowd to feel like they're doing something unusual rather then spending yet another evening staring at the fake titties and faux hair at Hemingways. That's the thing about the Drake, it provided a nice bit of cleanliness in an otherwise dirty area. It was never really marketted to actual hipsters - instead it's sorta like Main Street USA in Disney Land - come be a hipster for a night, but with clean bathrooms, more cocaine and less incense. Drake owner Jeff Stober even lives in the Village if you really want to understand his headspace about the whole thing.

But back to the event...

First encounter of the third kind, Faux Hillary runs into an old friend. The climber, as we'll call her, is, to put it mildly, intense. A day-trader at a downtown investment banking firm she once drunkenly slapped me with her Gucci bag and slurred, "how much do you make, I can get you a job where you'll be making $2000 a week." The Climber, a beautiful leggy blond, was truly out and about to show off her latest and greatest boyfriend, none other then the unemployed schlub of a very old money Toronto family. The type of family whose name adorns buildings at U of T but whose third generation is known not for their philanthropic spirit or shrewd business decisions... but still, a name is still a name.

Before leaving I had the good fortune to run into an even older friend, apparently a friend of the Climber. The Snob, if you will, works with the Climber at whatever banking firm pays that much money a week. Having not seen the Snob since elementary school we did the brief update on our lives (I enjoy throwing in the gratuitous mention of being gay at this point so as to spread that shit around the gossip world, "Do you know who is gay?" "I'm not surprised, didn't you think he was gay in elementary school?" "Ya but didn't he have a girlfriend?" "Do you think she knows now?" "Well maybe we shouldn't say something?")

The Snob asked me what I was doing, "i work in philanthropy at a not for profit." The Snob smiled... "Oh that's so sweet. I'm working for all the money and you're at a not for profit. That's so... cute."

Cute indeed.