Over the weekend, the 44-year-old rapper was spotted at the grand opening of the Yetunde Price Resource Center, an organization which offers assistance to victims of violence founded by Serena and sister Venus Williams.
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Back in 2015, Common spoke out about their 2010 breakup.
Last month there were also reports he was dating Regina Hall, but the “Go” singer shot them down saying they are just friends.
Serena Williams is one of the most famous tennis players in the world right now, dominating Wimbledon and taking on the Rio Olympics for 2016.
But, her boyfriend Alexis Ohanian is successful in his own right as well, with a net worth estimated at $4 million.
Sources close to TMZ said that Common, born Lonnie Rashid Lynn Jr., was "chatting" with Serena in the back of the center.
"Yeah, yeah it was kind of eventually a mutual breakup but she initiated it.
Sources said Common was seen getting up close and personal with the tennis legend at the event.
Neither have officially confirmed nor denied the dating rumors.
Thereafter, she started dating NBA star Amar’e Stoudemire, who was renowned for his playboy status.
The romance between the two athletes didn’t last more than a couple of months however, with both of them eventually moving on without hard feelings.
The first high profile romance rumours she was involved in was back in 2002 with American pro football player, Keyshawn Johnson, who was almost 10 years her senior.