On Meeting Anna Wintour, and Blowing It (Or, "How I Snuck into the Press Lineup at the MFA - and Almost Pulled It Off.")

Image via Conde Nast

The following is the completely true story of...The Girl Who Froze.

Can we talk about the time I met and interviewed Anna Wintour, and literally had nothing to say?

Yes, folks. Anna Wintour presented herself to me for questions, I froze, became a hollow piñata of a person, and indicated, by way of a blank look in my eyes paired with a tight pursed lip, that she should move along down the line to the next interviewer.

Let me set the stage for you: A few years ago, photographer Mario Testino came to Boston for the opening of his exhibit, "In Your Face," a sexed up, 122-piece retrospective he curated that included his most iconic images. Not surprisingly for those that know Testino's work, "exhibition" is a double entendre; on display were an ad he shot featuring a faceless model with her pubes shaved into a Gucci logo, a full-frontal portrait of a defiantly dangly Mickey Hardt and a shot of a scantily clad Kate Moss, among other works. (An adorably saccharine set of portraits of the Royal Family also made an appearance.) 

Where goes Mario Testino, so goes the entire fashion illuminati, as Beantown came to find out that night. Sure, Boston counts superhumans Tom Brady and Gisele as residents, and they occasionally pop up at events around town, like the Rag & Bone store opening on Newbury Street. But this particular party, held at the MFA on the day of the exhibition opening, flooded the city with more mile-high legs and chiseled cheek bones than the people of Boston knew what to do with. (Although the majority of people didn't know about this need-to-know-basis fete until the breathless press coverage the next day, including my own story, "'In Your Face,' and Out Of Reach" for Bullett.)

Model Joan Smalls and her abs / Image by Renata Certo-Ware

While I had been invited to the press preview at the museum earlier in the day, I was not technically supposed to be at the party that evening.

Which is not to say that I snuck in.

I prefer to say I finagled my way in. I didn't have an assignment, per se, but I desperately wanted to cover the event, and I knew if I could get in, I could pitch coverage and successfully land a story the next day. (The sometimes-misguided confidence of a newbie freelance writer, right?) 

It was in that spirit that I insinuated to the museum's press team that I had the green light for a story from one of my editors - I did not - et voila, a press pass with my name on it was printed up. (I still have the press pass.)

When I got to the museum that night and signed in with the greeters at the door, I was shown to my spot on in the press line on the red carpet next to the E! News crew, which I certainly did not expect - I genuinely, naively thought I would attend the party, and then write about the vibes and the exhibit. Easy as pie, if not a little conventional. Partying with celebs is great and all, but as a budding writer, getting to interview them is even better.

My fave Frenchie, Constance Jablonski / Image by Renata Certo-Ware

Since I didn't expect to be interviewing anyone, I obviously didn't have any questions prepped. I flipped through The Who's-Who pamphlet the MFA PR manager handed out, trying to act casual - unaffected, even - while I internally scrambled to come up with clever-cool queries for the likes of Karlie Kloss, Joan Smalls, and Alessandra Ambrosio.

As the doors opened, limos pulled up and models and scenesters flooded in, I pretended to act relaxed as I grilled them on working with Testino and their outfit inspo. More and more people were streaming in on the red carpet, and there wasn't time to politely look down the line to see who was strutting in next.

So when Anna Wintour paused in front of me, I not only didn't expect it (she wasn't on the interview roster!) but I also wasn't ready. One does not simply bump into Anna Wintour at a museum, right? Karlie, Joan, Constance and Alessandra, although beautiful, didn't give me shell-shock. They genuinely seemed as excited to be there as I was. 

But Anna, a veteran Vogue O.G. definitely had me shook. I would have liked at least a week to think of things to ask her, come up with ways to surreptitiously confirm or deny the Devilish rumors about her, and perfect a technique for casually slipping her my business card.

Instead of the confident, informed gal I could have or should have been, I reverted to Plan B - the tried-and-true "I Don't Even Care" with a subtle hint of "Someone (but who?) Is Forcing Me To Be Here," plus "This Is So Boring To Me Because I've Seen It All" and a dash of "I'm Friends With James Franco" air put on by Fashion Girls the world over.

So while my face was saying "And just what do you do in fashion?" my mouth was asking, in a slightly higher octave than normal "So, what do you think of Boston?"

Jesus take the wheel.

While obviously not inspired by the question, Wintour was actually pretty gracious and diplomatic.

"To be honest I’m not here enough often enough to have an opinion," (Editor's note: Ugh, obvi! Duh....why am I like this?) "But my mother was from Boston, and my grandfather used to teach at Harvard, so I obviously have a great affection for it and lots of fond memories. I used to come here as a child, but I don’t remember the fashion from back then.”

Ok, well-played. Anna Wintour 1; Renata Certo-Ware 0.

Time for my next groundbreaking question. "What do you think of Mario Testino?"

Someone please honor kill me.

Wintour responded with a massive smile. "He’s a great photographer, and it’s wonderful to see someone that’s worked so hard have so much success. I think what’s remarkable about Mario is that he just loves life.”

<Internal dialogue: "Better ask her the same question in a different way, just to be sure.">

Me: "What's it like working with Mario?" (I'm on a first name basis with the photog now.)

Anna Wintour: "I’ve known Mario for many, many years. We’ve gotten to know each other so well, we’re quite happy agreeing and disagreeing and the results are really amazing. He has amazing range.”

That's pretty much the meat of my riveting, eye-opening, soul-exposing interview with one of my heroes, Anna Wintour. I nodded and gave a tight little smile as she stood, patiently staring at me and waiting for me to ask another question (Read: she wanted to keep talking to me. Is she a sadist or something?)

Exactly nothing came to mind to ask her. Instead of chatting about travel, the latest Vogue cover star, the millions of Testino-shot spreads in the magazine's history, social events, heck, politics even, I thought of nothing but "Am I dead now?" and "Are you hiring? I'm great with people and really outgoing."

If I met her today, I think I would grill her on celebs' social media (the good, the bad and the overwrought); size and body image in the fashion world; Melania Trump: Good or Evil?; writing, and so much more. I would obviously also take a photo with her. We'd trade sunnies for the "Now let's take a silly one!" picture. 

I don't know what the lesson is here. I mean, I can't exactly advise readers to be prepared at all times to meet and question someone you really admire, to dazzle them with questions and stories and walk away best friends. My takeaway for future interviews is to try, try try to just act like I'm talking to a friend. I think the person on the other side of the red carpet will appreciate that more than having to answer queries about work and tourism.

Maybe if I ever have the chance again, perhaps I'll recount this very story.

You know, with a pinch of "But I like, don't even really care it's whatever."