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Cover Story: Serena Williams’s Love Match

Last January, on the eve of the Australian Open, Serena Williams handed her fiancé, Alexis Ohanian, a paper bag containing six positive pregnancy tests. It was just the latest surprise in an unlikely pairing: the world’s greatest tennis player and the geek co-founder of Reddit. From their first date—a magical six hours in Paris—to their plans for the baby’s arrival, this is the full love story.


This is a love story.

It wasn’t seamless, starry eyes at first light. There was a discovery, unexpected and shocking. There were moments of really getting pissed and the standard irritation that comes when one half of the whole kept leaving the suitcase in the hallway. But there were also moments of unplanned intimacy that is the only true kind of intimacy in a love story, soft touches and laughter and absurdity, because you need absurdity in a love story, since love is slightly absurd anyway, a feeling that, like eternity, is indefinable.

Which leads us, on the surface at least, to the seemingly mismatched pairing of 35-year-old Serena Williams and her fiancé, 34-year-old Alexis Ohanian. She is the beyond remarkable tennis player, although all superlatives are pointless. He is in the high cotton of high tech as the co-founder of the Web site Reddit, which has 234 million unique monthly users. They became engaged last December, after first meeting roughly a year and a half earlier, then found out in January that Serena was pregnant. They will be married in the fall after the birth of the baby.
With 23 grand-slam wins on the women’s pro tennis tour spanning nearly three decades—from her first, at 17 years old, in September of 1999, to her latest, at 35, in January of 2017, and the most in the open era—Serena is in the heart of every conversation concerning the best athlete of her time. “If I were a man, then it wouldn’t be any sort of question,” she told me. She may well be right, a society still conditioned to believe that men are better than women in everything except the superfluous.

Alexis, on the other hand, had never seen a tennis match until he met Serena, in May of 2015 in Rome. He knew so little about the game that the photo he excitedly posted on Instagram of her playing her first match in the Italian Open showed her foot faulting.

Serena plays a sport that requires the mental focus of instantaneously letting go of losing points and moving on because there are a lot of excruciating ones no matter how great you are, continual regrouping and re-inventing: dwell on them, you lose confidence; lose confidence and you lose. She is also superbly conditioned, given that a female tennis player may run about three miles in a match without the luxury of coming out of the game because you feel winded or lost too much money gambling with teammates the night before on the charter and would rather mope on the bench.

Alexis’s athletic history amounted to the level of a very gangly defensive tackle for Howard High School in Ellicott City, Maryland, far more interested in science fairs and programming and building Web sites. His skill at tennis is not one of potential; when Serena offered to give him a lesson, he turned it down so he could tell his friends that he once turned down a lesson with Serena Williams.

Serena has been romantically linked in the past to such rappers as Drake and Common. Once, when she and Alexis went to a movie in San Francisco, he got up from his seat to get popcorn, earning the admiration of the kid at the counter.

Before we get to how Serena and Alexis actually met, or a better sense of who he really is, or her reaction to the pregnancy and how she told him, it’s probably wise to spend a little time with Serena Williams to give our love story some context.
Let’s just get this out of the way right now: Serena Williams is the best tennis player in history, with an aggregate winning percentage of 85.76 percent and 72 tournaments won on the Women’s Tennis Association tour (including the 23 grand-slam victories in 29 singles finals, not to mention 14 doubles finals with sister Venus). She has earned $84,463,131 in career prize money and nearly twice that in endorsements and appearance fees.

Thirty is the point of no return for most female tennis players, but Serena has only gotten better since, with 10 grand-slam wins and almost running the four-tournament table—the Australian Open, the French Open, Wimbledon, and the U.S. Open—in 2015. She has been ranked No. 1 in the world longer than anyone other than Steffi Graf and Martina Navratilova, and is the obvious favorite to win any tournament she chooses to play in.

But then an unforeseen discovery left both Serena and Alexis in shock. Which is perfect for our love story, since a love story without drama is just another story.

JANUARY 2017

It began to unfold roughly a week before the beginning of the Australian Open, in Melbourne, last January, not that anyone would have known. After playing poorly in her first match of the year, in which she felt she had missed too many backhands, she went to the practice court and for two and a half to three hours hit 2,500 of them, by her estimation. If she missed one, she started over. She did roughly the same the next practice day.

But she felt a little different physically. She had unexpectedly thrown up at one point and her breasts had enlarged. She thought it might be hormonal. But her friend Jessica Steindorff immediately suspected something else and suggested a pregnancy test. Serena thought it was ludicrous.

Jessica worked on her for two days until Serena relented, and so Jessica went to a pharmacy and bought a pregnancy kit.

“I’ll take it just because (a) to prove you wrong and (b) because it’s fun, whatever. It’s like a joke. Why not?”

That Friday, as Serena was doing her hair and makeup for an event sponsored by the lingerie company Berlei, where she is a spokesperson for its line of sports bras, she took the test in the bathroom. “I put it down. I went back to finishing hair and makeup, was laughing, talking. I was getting the styling done. An hour and a half later, I went back to the bathroom and I totally forgot about it because it was impossible for me. . . . So I went back to get dressed and I went back in the bathroom and I was like, ‘Oh yeah, that test.’ ”

Jessica shrieked in delight at the results. Serena, as she put it, “did a double take and my heart dropped. Like literally it dropped.

“Oh my God, this can’t be—I’ve got to play a tournament,” said Serena. “How am I going to play the Australian Open? I had planned on winning Wimbledon this year.”

But never underestimate the Serena Stubbornness, as legendary in certain circles as her first serve. Beleaguered Jessica went back to the hotel pharmacy and bought five more test kits to further convince her.

Test No. 2: Positive. Test No. 3: Positive. Test No. 4: Positive. Test No. 5: Positive. Test No. 6: Positive.

Which is an opportune time in our love story to bring in the father and rewind to the moment Serena met Alexis and Alexis met Serena.

MAY 2015

Although in his early 30s, there is something still gushingly boyish about Alexis, six feet five inches and lean, with the moppish hairstyle that college tour guides favor as they extol all the wonders of the campus, including the mail room and the six-shooter cereal dispenser. In his case the corporate offices of Reddit, in the Union Square area of San Francisco, which look oddly unfinished—as if to say, Why be bothered with such trivialities in the hip high-tech culture?—twentysomething savants engrossed by their computer screen with heads slightly hunched, the way people used to look when they were engrossed by books, searching for the next Pied Piperian breakthrough and likely finding it before lunch is served on the second floor from a line of stainless-steel buffet trays winking and nodding with nutritious options.

Alexis was born in Brooklyn and raised in the nationally known planned community of Columbia, Maryland. Reddit’s origins go back to 2004 during his junior year at the University of Virginia, when he took an L.S.A.T. prep exam for law school, got about midway through the first section, and went to the Waffle House on Route 29 in Charlottesville to have waffles. He realized he did not want to be a lawyer, just as he had also realized that his real love was programming and building Web sites. He teamed with Steve Huffman, an engineering major, whom he had met the first day of freshman year.
They came up with the concept for Reddit, a Web site self-described as “the front page of the Internet,” in which users interact and respond to a myriad of topics that interest them. The number of users went up rapidly, and, in 2006, 16 months after launching it, he and Huffman, still in their early 20s, sold the company to Condé Nast (which also publishes this magazine) for a reported $10 to $15 million. The price was a fraction of what Reddit has been estimated to be worth today: $4 billion. Alexis sheepishly admitted that they may have sold the company a little early.

He left Reddit and went to Armenia, where his father’s family is originally from, to do volunteer work. He wrote a book called Without Their Permission: How the 21st Century Will Be Made, Not Managed, and traveled the United States for five months to promote it on a bus that went to 80 universities because he wanted to be on a bus that traveled around the country. He became a leading voice in stopping government intervention in the Internet. He helped invent the travel Web site Hipmunk. Several years ago, he and Huffman returned to Reddit as executive chairman and chief executive officer, respectively, the company once again independent.

Alexis and Serena met the way two people do in the best love stories: by chance. Actually, it runs a little deeper than that because, let’s face it, Alexis was initially considered by Serena and the others she was with to be an irritant they were hoping would just get the hint and go away.

The location was the Cavalieri hotel, in Rome, on May 12, 2015. That night Serena was about to play her first match in the Italian Open. She is not a morning person and usually doesn’t eat breakfast, but the buffet offering at the Cavalieri was beyond extravagant and Jessica was champing at the bit, so they went to try it along with longtime agent Jill Smoller, of William Morris Endeavor Entertainment, and Zane Haupt, who handles some business-development opportunities for Serena.

The buffet had closed down five minutes before the group got there, so their only recourse was to go to the pool area and sit at a table for four and order breakfast. Other people on Serena’s team were expected at an adjoining table.

The night before, Alexis had stayed up until one or two in the morning drinking at a café with Kristen Wiig and friends—Wiig was in Rome shooting Zoolander 2, and he knew her cousin, so he introduced himself. He passed out when he got back to the hotel, where he was staying for the Festival of Media Global conference, and was slightly hungover when he came down to breakfast. He too headed out to the pool area. Which is when he decided without thinking about it to sit at the table next to Serena, his only interest to get coffee and food and put on his headphones and work on his laptop. Which struck Serena and the others as a pain in the neck, since Alexis had a choice of other empty tables.
“I knew it was coming,” she says of the proposal. “I was like, ‘Serena, you’re ready. This is what you want.’ ”
“This big guy comes and he just plops down at the table next to us, and I’m like, ‘Huh! All these tables and he’s sitting here?,’ ” Serena remembered. Alexis recalled that the pool area was “not quite so empty.”

Then came the quintessential Australian accent of Zane Haupt. “Aye, mate! There’s a rat. There’s a rat by your table. You don’t want to sit there.”

Serena started laughing.

“We were trying to get him to move and get out of there,” said Serena. “He kind of refuses and he looks at us. And he’s like, ‘Is there really a rat here?’ ” At which point Serena remembers the first words she ever said to him.

“No, we just don’t want you sitting there. We’re going to use that table.”

“I’m from Brooklyn. I see rats all the time.”

“Oh, you’re not afraid of rats?”

“No.”

Which is when Serena suggested a compromise and invited Alexis to join them.

Which is when Alexis became “98 percent sure” that the person asking about his rat tolerance was Serena Williams. He knew generally about her accomplishments on the court. But Alexis, an avid pro-football-and-basketball fan, had “never watched a match on television or in real life. It was literally the sport—even if ESPN was announcing tennis updates, I would just zone out. . . . I really had no respect for tennis.”

He did keep this to himself.

Serena asked about the tech conference and whom Alexis had come to hear speak. He later described the question as a “softball lobbed over the plate” that even he could hit out of the park.

“Actually, I’m here to speak.”

Alexis told her about Reddit. Serena knew nothing about it but acted as if she did, and said she had been on it earlier in the morning.

To which Alexis asked, “Oh, were you? What do you like about it?”

To which Serena gave a very long “Wellllll . . . ” and was saved by Jessica and Jill chiming in.

Serena Williams has long been queen of the tennis court, but her success also extends to business, fashion, and philanthropy. Watch the video below to see some of her biggest career achievements.

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