Before Meghan Markle became the Duchess of Sussex and Prince Harry's wife, a former ESPN host had his sights set on her. Ryen Russillo, 49, once tried to woo Meghan after they met at a celebrity flag football game during Super Bowl weekend in 2014, according to UsWeekly.

Speaking on The Bill Simmons podcast, Russillo recalled: "We played in a celebrity flag football game together and it was all of the [Sports Illustrated] swimsuit models. So, nobody was really paying any attention to Markle."

The star-studded match included former NFL stars, The Vampire Diaries' Nina Dobrev, Black Panther's Michael B Jordan, and Sports Illustrated models like Chrissy Teigen, Nina Agdal and Hannah Davis.

"I was like, 'That's my lane. She's probably doubting herself a little bit right now,'" Russillo said. "She's never been more obtainable."

This was just before the premiere of Suits season 4 and two years before Meghan began dating Prince Harry. After the game, Russillo decided to take a chance and sent Meghan a cheeky direct message.

Russillo described the approach as a very soft sell, saying: "It was, 'Hey, I know the new season of Suits is coming out if you ever want to come on the show to promote it.' It was really professional."

Despite this, he confessed to having an ulterior motive, stating: "It was like a gauging of interest," and "Like, if I got an emoji back, who knows? " Meghan did respond to his message, but not in the way he had hoped. "It was ice cold," Russillo remembered.

"It was, 'Oh, I don't know anything about sports, but thanks for the offer.'" In the end, Russillo admitted: "It didn't work out."

However, Meghan did gain something from the celebrity flag football game - a lifelong friendship with Serena Williams.

Recalling their first meeting, Meghan wrote on her blog The Tig in August 2014: "When Serena Williams barrelled in my direction this past February at an event, nails done, hair done, everything did, I'll be honest and say I looked behind me to see who she was running to. It was Serena Williams, after all."

Markle went on to say: "We hit it off immediately, taking pictures, laughing through the flag football game we were both playing in, and chatting not about tennis or acting, but about all the good old fashioned girly stuff.

"So began our friendship. She quickly became a confidante I would text when I was traveling, the friend I would rally around for her tennis matches, and the down to earth chick I was able to grab lunch with just a couple weeks ago in Toronto."