Drake-Serena Williams Dating Rumors: 'Back To Back' Rapper's 'Playboy Lifestyle' Hurt, Struggles 'To Clean Up The Mess'

Drake’s “playboy lifestyle” has been affected after his pictures with Serena Williams landed on the Internet last month. The rapper is now “trying to clean up the mess” and is struggling to get things right with his “side chicks,” according to Hollywood Life.

“Drake getting caught with Serena really ruined his game with the plethora of girls he has at his disposal,” a source close to the Canadian rapper told Hollywood Life. “Now that Serena has asked Drake to stay away while she attempts to win the Grand Slam, he has been caught with his pants down trying to make it right with Serena and his side chicks at the same time. His playboy lifestyle bit him in the ass when those pics with Serena came out, and now he is trying to clean up the mess.”

The 33-year-old tennis player and the “Back To Back” rapper sparked dating rumors after they were photographed locking lips at a restaurant in Cincinnati, Ohio.

On Wednesday, reports surfaced that Williams’ close friend Kim Kardashian is advising her on ways to win over Drake.

“Kim and Serena have known each other for a while and they decided to reconnect while in NYC. Kim has gotten to know Drake well through Kanye,” another source told Hollywood Life. “She knows what a player he is and has a good idea of what it will take to win his heart. Kim also has a pretty good idea on how to snag a huge rap star since she did it herself. Kim did it by playing hard to get.”

Earlier, Williams’ family members warned her to stay away from Drake as they feared he would leave her with “a broken heart,” according to media reports. However, the Wimbledon winner’s friends reportedly approve of the way the 28-year-old rapper treats her.

A source told E! News that their relationship is “heating up,” but they’re trying to keep it as private as possible.