I found what I think qualifies as the most awkward moment in the history of time.
You can read the background info in this article or
but here is the gist of what happened to casino magnate and millionaire
Steve Wynn and the Picasso painting he had just agreed to sell:
Wynn had just finalized a $139 million sale to another collector of his
painting, called "Le Reve" (The Dream), when he poked a finger-sized
hole in the artwork while showing it to friends at his Las Vegas office
a couple of weeks ago. (MSNBC)
Can I just say that $139 million is about the amount I would pay (if I had it) to ensure that I would never, ever,
ever, for the rest of my life
have to be in a situation as awkward as how it must have been for the
friends Wynn was showing the picture too when that happened? Nora
Ephron was there and blogged her account of the moment for good old Huffpo, and it was excruciating just to read it. A selection:
The Ganz collection went up for auction in 1997, Wynn was saying --
he was standing in front of the painting at this point, facing us. He
raised his hand to show us something about the painting -- and at that
moment, his elbow crashed backwards right through the canvas.
There was a terrible noise.
Wynn stepped away from the painting, and there, smack in the middle
of Marie-Therese Walter's plump and allegedly-erotic forearm, was a
black hole the size of a silver dollar - or, to be more exactly, the
size of the tip of Steve Wynn's elbow -- with two three-inch long rips
coming off it in either direction. Steve Wynn has retinitis pigmentosa,
an eye disease that damages peripheral vision, but he could see quite
clearly what had happened.
"Oh shit," he said. "Look what I've done."
The rest of us were speechless . . . I felt that I was in a room where something very private had
happened that I had no right to be at. I felt absolutely terrible.
lord. Anyway, by all accounts the situation appears to have been
resolved about as nicely as could have been hoped, but if I had been
there when it happened I never would have lived to find that out. I
would have died of sheer awkwardness. Multi-million dollar
As a mental exercise, I've been trying to decide what I would
have said/done had I really been there. Obviously, the best plan would
have been to stay quiet and wait for the moment to pass, but if there
is one thing I know about myself it is that I cannot handle long
silences. Any time my brain senses a conversational lull of more than
three seconds, it reflexively spits something out without my conscious
consent. I think this is because somewhere in my mental chain of
command, the "JUST SAY SOMETHING, ANYTHING" synapse is fatally and
erroneously wired to fire seconds before the "MAYBE TRY BEING
APPROPRIATE JUST THIS ONCE" synapse. It is the perfect formula for
creating stiflingly awkward moments, like this recent exchange:
Perfectly friendly and nice person sitting across from me at a happy hour: So, how come you've never been to one of our happy hours before?
Me: Because I don't really like meeting new people.
huh? Way to keep up the conversational vibe. I felt so bad for the
poor soul who had tried to strike up a conversation with me and was now
doomed to try and spend the rest of the happy hour looking in every
other direction than at the psycho girl directly across from him, the
one who apparently goes to happy hours in the hopes of not meeting any
Anyway, back to the $139 million painting. I tried to recreate
the scene in my head as if I were there, and I decided that what would
have probably happened is that I would have nervously started to make a
joke, realized how innappropriate I was being, and stopped dead in the
middle of my sentence to make the situation even more awkward then
ever. Like, "[Nervous laugh] Well hey, I'm sure it's nothing a little
Scotch tape won't . . . [Clears throat. Looks down] I'm so sorry."
I can't even tell you how uncomfortable I am to even imagine that.