Serena Williams and Alexis Ohanian’s First Date Featured A ‘Questioning’ Session by Her Agent and Assistant

Serena Williams is a formidable opponent on the tennis court, but she brought in her team to thoroughly investigate Alexis Ohanian’s relationship.

In the most recent episode of her ESPN+ documentary series, In the Arena, Williams, 42, revealed that she went on her first date with Ohanian, 41, in 2015 with her then-assistant and agent, Jill Smoller.

Ohanian recalled, “It was like two hours of questions and interrogation.” “Do I have children? “Am I married?” (Williams and Ohanian met while lodging at the same Rome hotel in May of 2015.)

“Nothing was off limits,” the Reddit cofounder remarked during the tense dinner. “I was on the other side of the table with Serena, her assistant, her agent, and they just kept asking me questions,” Ohanian recalled.

Similar details about the first date were provided by Smoller, 59, who told the cameras, “I totally tried to get the book on him right away.”

Williams was completely cool with her agency questioning her husband at the time. “Jill asked him directly, ‘What’s going on with your girlfriend?'” And he was like, ‘I’m not dating,'” Williams remembered.

He then announced that he and she had broken up. The 23-time Grand Slam winner laughed, “I was like, ‘OK, now he’s not being this beast,’ and that changed things when he said that.”

During the docuseries, Williams and Ohanian shared their first text conversation in which he wanted to take her out to dinner. Williams responded, “Okay, but I’m going to bring my agent and my assistant.”

Their bond was evident even though Ohanian was the center of attention during their first date. Williams said, “He started talking about Iron Man and Marvel during dinner, and that’s the way to my heart.”

Ohanian stated that he had “watched a few movies” and that his passion of the superhero genre “wasn’t just […] superficial.” “I have deeply studied the text and I have strong opinions about this lore,” he said in his explanation.

Meanwhile, Smoller immediately saw the connection between Ohanian and her longstanding customer. She remarked, “It was really fascinating because they had similar interests.” “Jesus, at last, she gets to interact with people who share her interests.”

Ohanian made fun of the fact that he “passed the test” with Williams’ agent and assistant at the time, and he wasted no time in asking her out on a formal date that didn’t require chaperones.

“Hey look, last night was fun, but I’m going to pick you up,” I texted her the following day. It’s simply going to be the two of us spending the day together in Paris,” he remarked.

The couple’s history ends here. In December 2016, Ohanian proposed to Williams in the same Italian hotel where they had originally met.

After welcoming Alexis “Olympia” Jr. as their first child in September 2017, the couple got married in November of the same year. Adira River, Williams and Ohanian’s second daughter, was born in August 2023.

“Olympia is my constant companion. I used to wonder all the time, “How could I love anything as much as I love @olympiaohanian?” before I had my second child. On August 15, Williams shared a reflection on her life as a mother of two on Instagram.

Then Adira appeared. She is incredibly unique, hilarious, loving, lovely, and resilient.

“You see, God makes your heart get bigger,” she exclaimed. Since my affection for Olympia has not diminished. Simply said, my heart has multiplied in size and I can love more now!”

Leave a Comment