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Caption Contest: Anna Wintour's Awkward Embrace with Charlie Rose

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Anna Wintour rarely gives more than one facial expression — tight lips, straight stare (you know which one we’re talking about). It’s rare to see the legendarily icy Vogue editor-in-chief emote at all. So when we spotted this photo of her and Charlie Rose on the red carpet at The Hollywoood Reporter‘s event celebrating the 35 most powerful people in media, we were delighted — and decided to turn it into an in-office caption contest.

Anna Wintour and Charlie Rose
Neilson Barnard/Getty

Wintour’s face is priceless — part terrified, part surprised, part confused. And the grasp between the two is also intriguing. Below, our thoughts on the photo, with a very special appearance from Wintour herself — or rather, Ryan Raftery, who plays her in a one-man musical.

“Hold me, Charlie. Kris Jenner just walked in.” Ryan Raftery, mastermind behind the one man show “Ryan Raftery is the Most Powerful Woman in Fashion”

“My God, Charlie, did you just say you’re wearing Yeezy x Adidas under your clothes?!” –Alex Apatoff, Senior Style Editor

“Did you see those skants Kendall has on?” –Brittany Talarico, Style News Editor

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“I wish I had my very own Sébastien [Karl Lagerfeld’s bodyguard] to intervene. Karl doesn’t do selfies, Anna doesn’t do hugs.” –Colleen Kratofil, Style Reporter

“I’m not sure I can get you the closing spot in Oscar de la Renta, Charlie. That usually goes to Karlie Kloss. But I’ll see what I can do.”

“It’s Jennifer Grey and Patrick Swayze 2.0 — don’t freeze before the lift, Anna!” –Jackie Fields, Beauty Writer/Reporter

“Kiss me, Charlie! Kiss me!” –Sarah Kinonen, Editorial Assistant

“Oh, Charlie, I’m sure I can get some contouring products for you out of the Vogue beauty closet. I’m just not sure how much it will help?”

How would you caption the photo? Sound off below.

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