What Happened at Anna Wintour’s Dinner for Barack Obama?

Last night in Greenwich Village, Harvey Weinstein, Georgina Chapman, Donna Karan, Bee Shaffer, Tory Burch, and Calvin Klein gathered with fellow wealthy liberals at Anna Wintour’s house for dinner with Barack Obama to raise money for the Democratic National Committee. Attendees each paid $30,400 to attend, but no reporters were allowed inside, which is what the Obama administration does when the president just hangs out but doesn’t give speeches. So we may never know what happened in Anna’s house last night for the hour that Obama was there, but we can make it up in an imaginary scene!

Barriers on Sullivan Street in Greenwich Village are cleared for a motorcade approaching from uptown. It putters onto the street and parks outside a stately light-blue townhouse. The president exits his vehicle, his face shiny from the sticky New York humidity. Secret Service escort him to the front door. They knock. One of Anna Wintour’s bodyguards opens.

Anna Wintour: Lovely to see you, Barack. You’re only two years late.
Barack Obama: Hello, Anna. Thank you for giving the Democratic Party’s wealthiest and most fashionable supporters a private place to give us their money. Though I do always feel a bit bad about shutting down the entire neighborhood.
Anna: Don’t be silly — it’s the gated community I’ve always dreamed of! Besides, you’re in a safe space, here, darling, not the people’s space. No guilt from excess here.
Barack: Ho ho, you’re right! Man, it sure does smell great in here — did you sprinkle lavender oil on the banisters?
Anna: Ugh, too messy. I just had my private army of scientists install miniature lavender fields in my new air-conditioning units so that we may be constantly showered in fresh lavender air.
Barack: Man, you really know how to throw a party. I just can’t coordinate this kind of stuff — but you know how I struggle with simple things like wearing pants that people won’t make fun of. Air conditioners filled with genetically altered lavender? Forget about it.
Anna: Right, well it’s a good thing you’re the president — otherwise, those “clothes” you speak of certainly would have been a bit of a wedge in our friendship. However, while we’re on the subject of how you look, I might suggest you take a cue from your wife and travel with a makeup artist. [Whispers.] Your face is kind of shiny.
Barack: Oh no! I have shiny face again? My old-fashioned handkerchiefs just aren’t very absorbent, I supposed.
Anna: All I’m saying is that if you came over more often …
Barack: What? That bad?
Anna: We could go over a few things: powder, tailoring, facials.
Barack: I do have to say, this house is pretty nice. I feel like I’m on the set of a Meryl Streep movie!
Anna: It’s no White House, but at least it’s, well, up to date, decorating-wise. Nothing you’ll find here is hundreds of years old — except the many bottles of wine and Champagne I’ve arranged for us to consume, of course.
Barack: Awesome! Only I don’t drink on school nights. Even if I did tape The View this morning with Elisabeth Hasselbeck. Say, what’s for dinner?
Anna: Kobe beef served in truffle bowls.
Barack: Ooh, I haven’t had a bread bowl since the chowder in Maine! Glad I didn’t eat at The Four Seasons.
Anna: No no, not bread — it’s a half of a truffle sourced by my private army of truffle pigs. Then the chef scoops them and discards the innards. I hear people sometimes request their bagels get similar treatment.
Barack: Oh, Anna, you are truly high-low, just like your magazine. Really brings a tear.

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What Happened at Anna Wintour’s Dinner for Barack Obama?