Late one September evening, after the commuters have emptied out of midtown Manhattan, a couple sits at the bar at The Grill, where the old Four Seasons used to be. A cold rain has washed away the summer, and the streets are dark and gleaming. Inside, the cavernous space is gold and dazzling. Tuxedoed waiters glide by, pushing trolleys. The man drinks a glass of red wine, a nice Brunello. He and the woman smile as they talk, easy in each other’s company.
The woman wears a navy Chanel dress, with a neckline that accentuates her shoulders. Her blonde hair is brushed back from her face, and her blue eyes are clear as water. Twenty-eight years old, she sits erect, confident and composed. On her left hand, she wears an eye-catching engagement ring; on her right hand, a ring that matches one she bought for her mother. The man is older, 35, and unusually tall; he carries himself with an athlete’s casual grace. He has light brown hair and the suggestion of a beard, and he wears Tom Ford jeans and a dark Louis Vuitton shirt. A passerby might recognize the woman as the tennis champion Caroline Wozniacki and the man as the former NBA All-Star David Lee, but no one pauses to stare, so perfectly are they suited to their surroundings.
It is, as usual, a whirlwind trip through the city. They have come up from Miami, where they own a condo and where they retreated after Wozniacki lost in the second round of the U.S. Open on a brutally hot and humid day two weeks before. Next, they will travel to Tokyo for a tournament. They live the better part of their lives out of suitcases, but they are not ones to complain about the grind. Still, for Wozniacki in particular, the demands are endless: sponsors, press, photo shoots, not to mention tournaments and training. She has a strong sense of who she is, what she likes, and what she wants. “I want to be a good fiancée, a good daughter, a great tennis player,” she says, her voice speeding up. But what she wants is not easy to achieve. “I can’t think too far ahead,” she says. She focuses on the next year, the next month, or even the day or hour. “At this point, I keep short goals.”
Still, they talk about their future, the way engaged couples do—the way couples pick names for their unborn sons and daughters, or build imaginary houses with pools and apple orchards and plumbing that never breaks. “I would love to have a big family and probably step away a little from the spotlight,” Wozniacki says. Eventually she might want to do something in fashion, drawing on her experience working with Stella McCartney for Adidas, or do some charity work or something involving animals. “Acting could be so fun,” she said. “Push my limits a little bit.”
The two are settled into a plush banquette now, with a view of the dining room. The table fills with plates of food: tender filet mignon for her; bowls of butter dumplings and sautéed spinach; a large steak for him, still sizzling with heat; and hash browns, which Wozniacki has ordered and Lee sneaks forkfuls of. They recount stories from the past year, beginning with the moment in October when Lee decided to retire after twelve seasons in the NBA (he played for five teams—and won a championship with the Golden State Warriors in 2015). “I really came to the conclusion that the reason I’d keep playing was so that I could sit in this interview and say I played fourteen years instead of twelve,” he says. “Ego-wise, I’m not a Hall of Famer, so what stats am I trying to pad, and for what reason?” He called Wozniacki and told her that he was coming to Singapore, where she was set to play in the WTA year-end championship. “I said, ‘Guess what, babe, my schedule just opened up,’ ” he remembers with a laugh. On the layover in New York, he picked up an 8.88-carat ring (can you guess Wozniacki’s favorite number?).
The hard part, it turned out, wasn’t popping the question—it was asking permission from Caroline’s father, Piotr Wozniacki, who taught her to play when she was a little girl growing up in Denmark and has been her coach ever since. In Singapore, after Wozniacki secured a place in the semifinals, Lee and Piotr met for a drink. The two men had become close, but Lee’s hands still shook with nerves. “We’d had every conversation in the world,” Lee says, “but to take it from ‘Wow, what a beautiful day outside,’ to ‘So!’ ” Piotr was thrilled. When Caroline joined them, she asked what was going on, and they told her they were celebrating her trip to the semifinals. “I was like, ‘I guess you’re taking it up a few notches! I like it!’ ”
Wozniacki won in Singapore, defeating Venus Williams in the final, and then she and Lee headed to Bora Bora for vacation. He organized a private dinner cruise, and they watched the sun set over the South Pacific. “Isn’t this beautiful?” Wozniacki remembers saying, and Lee grew so quiet that she thought something was wrong. “One second,” he said as he fumbled inside his backpack.
“It was good execution,” Lee says, self-deprecatingly, and then turns serious. “Even if we had just had had a normal dinner—it would have been one of the most beautiful things we’d ever done.”
“It was like, we’re killing it right now,” Wozniacki cuts in. “Tennis, life, everything!” Her voice is playful, but with an undercurrent of genuine amazement. Who could disagree?
Two months after the proposal, she would play in the final of the Australian Open against Simona Halep. Wozniacki had never won a grand slam, and the winner would take the number one ranking. It was one of the best matches of the year, a dramatic three-set heavyweight bout—and Wozniacki won. As she walked off the court, the crowd sang “Sweet Caroline.” Lee was there to meet her in the locker room. It was a fairy tale, a dream.
Wozniacki’s dream as a girl had been to become number one. It happened for the first time in Beijing in 2010, when she was 20, after she beat the Czech champion Petra Kvitova. The next day, she went onto the practice court with her father to warm up for a quarterfinal match. “My dad said, ‘Move your feet,’ ” she remembers. “And I’m like, ‘I’m number one in the world and nothing has changed?’ And he said, ‘What did you expect?’ ”
She couldn’t admit that the pressure was hard on her. “You can never show vulnerability; you can never say, ‘I’m not feeling good.’ ” So she swallowed it. The attention on her, especially in Denmark, was relentless. “Every day, getting questions: You’re number one, but you’ve never won a grand slam. Do you think you deserve it?” What was she supposed to say? What was she supposed to think? “I had moved up through the rankings really quickly,” she says. “So I started asking myself, Am I good enough? Is this luck?”
She held on to that number one, week after week, month after month. But the criticism did not go away, and finally, she relinquished the ranking after a string of injuries. She fell out of the top ten and made little impact at slams. For a time, she was better known for appearing in Sports Illustrated’s swimsuit edition than for her results on the court. Her life was tabloid fodder. At the end of 2013, she became engaged to the golfer Rory McIlroy, who then broke up with her after the wedding invitations had been sent out. It was a painful time.
But she turned it around—her tennis, her happiness, her life. She met Lee at a dinner party in Miami thrown by a mutual friend, and they stayed in touch. Eventually they started dating. She became a fixture at his games, joining the group cheers, giving high fives. (In her player’s box, on the other hand, “it’s like a military operation,” Lee jokes. “I don’t even check my phone.”)
He understood her determination, her logical way of thinking through choices, her drive. He understood, too, the strangeness of achieving your dreams—an NBA Championship—and still wanting something more. “I’d thought, Once I get that big contract, all my problems will go away,” he says. But of course, that’s not the way the world works.
At first, Lee imagined that he might have something to say about her tennis, too (he’d grown up playing). “I really thought I had something to offer strategy-wise,” he jokes. They did play once, so that she could put him in his place. These days, he contents himself with lessons and knows that he is simply there to be loyal and supportive—come to every match he can, catch the ones he can’t online. Off the court, though, she has learned from him: learned to step back, not to hold so tightly to her expectations, to let things happen as they come. When she was injured, especially, he reminded her that she shouldn’t punish herself. She was allowed to be proud of what she had accomplished.
It’s getting late. The tables are turning over at The Grill. They tell stories about each other as the buzz of the post-dinner crowd grows a little louder. There was, for instance, the time that Lee—making an effort to take more of an interest in fashion—bought an $800 T-shirt, which Wozniacki unknowingly threw in the wash. “He was like, ‘We can never wash it! It won’t fit!’ I thought it was funny. I think he thought it was a little less funny than I did,” she says. They talk about his learning Polish, Wozniacki’s native language, to become closer to her family.
They talk about the wedding. They imagine moving to be closer to Wozniacki’s family in Europe. They talk about how simple their lives are, in some sense, despite all the parts and people moving around them—how they like to go to the movies, or stay at home and watch TV, or work out in the morning and grab breakfast together at a diner.
As the dinner crowd leaves, the tone of the room changes. There are hints of uncertainty. For months, Wozniacki has been feeling drained and achy. The morning after a match in Montreal, she woke to find that she couldn’t raise her arms to comb her hair or brush her teeth. Her knees were hurting, her hands swollen. “The doctors said, ‘You’re fine,’ ” she later tells me. “I said to myself, I know I’m not fine.” Finally, a series of blood tests taken around the time of the U.S. Open confirmed rheumatoid arthritis. It will take a few months before she feels comfortable announcing it publicly. “For me it was important to know that I can handle this, I can still be a great athlete,” she says. It had been a shock. “You think you’re the healthiest and the strongest, and you don’t think something like this can hit you,” she says. “It doesn’t discriminate. It doesn’t matter whether you’re young, old, healthy, or not.” Still, she is young, healthy, and strong. She is determined to look forward, and think positively.
And so is he. There is so much to look forward to, after all—after basketball, after tennis, when the spotlight is off, when the only people watching them are each other. “Whether that’s fifteen minutes from now, or fifteen years from now, whatever she decides—all I’ve told her is, ‘I’m supporting you,’ ” Lee says. “It’s just a matter of doing it on your terms.”
In this story:
Sittings Editor: Phyllis Posnick.
Hair: Thom Priano for R+Co haircare; Makeup: Fara Homidi.
Tailor: Christy Rilling Studio.