is a boss on the tennis court, but when it comes to her relationship with , she brought in her squad to vet him.
Williams, 42, recalled during the latest episode of her ESPN+ docuseries, In the Arena, that she brought her agent, , and her then-assistant on her first date with Ohanian, 41, back in 2015.
“It was, like, two hours of interrogation and questions,” Ohanian remembered. “Do I have kids? Am I married?” (Williams and Ohanian met in May 2015 while staying at the same hotel in Rome.)
The Reddit cofounder said, “Nothing was off limits,” during the nerve-wracking dinner. “Serena, her assistant, her agent and then me on the other side of the table and they just bombarded me with questions,” Ohanian recalled.
Smoller, 59, had a similar account of the first date, telling the cameras, “I totally tried to get the book on him right away.”
Williams was totally on board with her agent grilling her now-husband. “Jill asked him straight up like, ‘What’s up with your girlfriend?’ And he’s like, ‘I don’t have a girlfriend,’” Williams recalled.
“Then he said that he had broken up with her. It changed things when he said that because I was like, ‘OK, now he’s not being this beast,” the 23-time Grand Slam winner said with a laugh.
Williams and Ohanian showed their initial text exchange when he asked to take her out for dinner during the docuseries. “OK, but I’m gonna bring my agent and my assistant,” Williams replied at the time.
While Ohanian was in the hot seat their whole first date, their connection was hard to miss. “During dinner he started talking about Iron Man and Marvel, and that’s the way to my heart,” Williams gushed.
Ohanian noted that his love of the superhero genre “wasn’t just […] superficial,” or that he had “watched a few movies.” He explained that he has “deeply studied the text and I have strong opinions about this lore.”
Smoller, meanwhile, saw the spark between her longtime client and Ohanian instantly. “It was so fascinating, because they both loved the same things,” she said. “I’m like, Jesus, she can finally talk to people who like the things she does.”
Ohanian teased that he “passed the test” with both Williams agent and then-assistant and didn’t waste any time asking her out on a proper date — without any chaperones.
“The next day, I texted her, like, ‘Hey look, last night was fun, but I’m going to pick you up. We’re going to spend the day together in Paris and it’s just going to be us,’” he said.
The rest is history for the couple. Ohanian proposed to Williams in December 2016 at the same hotel where they first crossed paths in Italy.
The pair welcomed their first daughter, Alexis “Olympia” Jr., in September 2017 and proceeded to wed that November. Williams gave birth to her and Ohanian’s second daughter, Adira River, in August 2023.
“Olympia is always there for me. Before having a second child, I always wondered, ‘How could I love anything as much as I love @olympiaohanian?'” Williams wrote via Instagram on August 15, reflecting on her life as a mother of two. “Then Adira came along … she is so special, so fun, so funny, so loving, so sweet and so strong!!!”
She gushed, “You see, God makes your heart get bigger. Because my love for Olympia has not dimmed. My heart simply now is doubled in size and I have a greater capacity to love more!”
