Novak Djokovic is currently ranked the No. 1 men’s singles tennis player in the world. I last played tennis when I was 12. Yet somehow, shortly after midnight last Thursday, I found myself staring down the barrel of the Djokovic serve on a court in one of Milan’s largest sports arenas.
“Are you ready?” he called, before throwing, flexing, and then smashing the ball in one sinuous movement that, had I not been at its receiving end, I would have relished witnessing as a symphony of human physical grace.
My reply? Not so much. I didn’t see the ball, just a vague green laser beam, but I sure felt the wind of it passing. And as I crouched at the baseline and prepared to answer a second serve, I issued silent thanks that at least I’d already had children.
“How did this happen?” incredulous friends have been asking me ever since. It started last Wednesday as I trooped into the Gucci show, following the opening lunch for Milan Fashion Week in the presence of Italy’s Prime Minister Matteo Renzi. I was shooting the breeze with Vogue Runway Director Nicole Phelps, discussing the U.S. election, the future of fashion, and the end of Brangelina—all the big stuff. As we rounded the last banquette by our block, I noticed that VogueEditor in Chief Anna Wintour was beckoning me over for a word.
“Luke,” she said, “do you play tennis?”
“No,” I replied firmly. “But I’m pretty good at ping-pong.”
Anna: “Would you like to play tennis?”
Me: “Umm, okay sure?!”
“Great,” she said, gesturing slightly to her right. “Would you like to play tennis with Serena Williams?”
My eyes flicked to the right, and there, wearing a Gucci bomber and a terrifying grin, was Serena Williams. I felt my spirit leave my body a little.
“Great,” said Anna. “Then it’s all set. I bid for a game with Serena, but I can’t make it. So I’d like you to go along in my place and write an article. I think it’s set for 8:30 p.m.”
I stumbled back to my seat. It was well after the Fausto Puglisi show, and only 90 minutes before we were supposed to play, that it dawned on me that I didn’t have the address. Finally I got the address and, with my shorts and trusty Arsenal T-shirt in my bag, headed to the venue, a place called Mediolanum Forum. “Wow,” offered Vogue.com’s cameraman, Nico. “That’s quite a big stadium. The Rolling Stones play there.” That seemed a little strange. Then I got a WhatsApp message from a friend: “Did you know Serena is playing in a celebrity tournament live on Sky TV tonight?” A quick check revealed a horrible truth. Serena was playing as part of a two-day exhibition match series for the Novak Djokovic Foundation. Anna had won a celebrity auction to play her there—and I was her patsy.
“Anna,” I emailed. “I have just discovered it is a celebrity tournament with thousands in the audience. I am going for it—but argh!”
“Oops,” she replied. “Forgot to mention. Wanted to make sure you would go.”
And that is how I ended up sitting two hours courtside watching Serena Williams fire off 180 km/h serves in front of a roaring crowd and wondering what the hell was going on. What would all these Italian tennis fans make of a junior fashion editor failing to return a shot?
In the end, the fortunes wheeled my way. The actual “celebrity” bit of the tournament ran over. The cameras shut down. The crowd left. My heart stilled. Williams’s agent, Jill, explained that, as she’d been playing for more than three hours, Williams needed to shower and get some sleep. We could play another day.
Which is when Novak Djokovic sauntered on court and offered to take Serena’s place. I would have loved to have played her—although not live on Italian television—but playing him was an equal privilege. We had a fascinating conversation about the balance between calmness and focus, “The Zone,” which he tries to achieve while playing. He even gave me a serving lesson. And what you won’t see in the accompanying video is that I returned a Djokovic serve.
Okay, my return was out by a whisker. But it went over the net! Which, when life chucks you a curveball as crazy as this one, is the best you can hope for.