Before Meghan Markle was a Duchess, former ESPN host Ryen Russillo hoped things might go down in the DMs.  Russillo, 49, who now works for The Ringer, recalled meeting Markle, 43, over Super Bowl weekend in 2014. “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,” Russillo said on the Thursday, December 5 episode of “The Bill Simmons Podcast.” The game featured former NFL stars playing alongside celebrities like Markle, actress Nina Dobrev and actor Michael B. Jordan, and Sports Illustrated models like Chrissy Teigen, Nina Agdal and Hannah Davis.  Ryen Russillo, Meghan Markle. Suits’ Rachael Harris Says It’s ‘Great’ Costar Meghan Markle ‘Happened to Find a Nice Guy’ “I was like, ‘That’s my lane. She’s probably doubting herself a little bit right now,’” Russillo remembered. “She’s never been more obtainable.” The flag football game was three months before the season 4 premiere of Suits, the USA Network show on which Markle formerly starred, and two years before she started dating Prince Harry.  After she and Russillo parted ways on the gridiron, he said, “I shot her a DM.” “It was a very soft sell,” Russillo explained. “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.” Still, Russillo couldn’t help but admit that some ulterior motives were in play.  “It was like a gauging of interest,” he said. “Like, if I got an emoji back, who knows?” Markle did respond to Russillo — but it didn’t lead to any future meet-ups for the pair.  “It was ice cold,” Russillo said of her DM response. “It was, ‘Oh, I don’t know anything about sports, but thanks for the offer.’” Prince Harry and Meghan Markle: A Timeline of Their Relationship Ultimately, Russillo said, “It didn’t work out.” While Markle didn’t leave the celebrity flag football game with a new potential love interest, she did meet a superstar athlete who would become one of her best friends: Serena Williams. “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 wrote on her blog The Tig in August 2014.  Markle continued at the time, “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.”