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Entity reports on the engagement between Serena Williams and Reddit co-founder.

Now that tennis ace Serena Williams is engaged to Reddit co-founder Alexis Ohanian she will be hoping this love match works out better than her past romances.

While she has dominated the Grand Slam circuit for years, Serena, 35, has found the game of romance harder to play.

“I’m really shy. I get nervous that I will say the wrong thing,” she told Vogue about the way she behaves around guys she likes.

But all has worked out with husband-to-be Ohanian, 33, a Brooklyn-based internet entrepreneur, activist and investor with a net worth of $4 million.

And, after a 15 month romance, where did she announce her engagement? On Reddit, of course.

Comment from discussion I said yes.

READ MORE: Serena Williams Gets Candid About Body Shaming and Sexism in Sports

As she prepares to walk down the aisle with him, ENTITY looks back at some previous romances that didn’t go the distance.

1 BRETT RATNER

Entity reports on Serena Williams's former relationship with Brett Ratner.

Serena dated the film director, most famous for the “Rush Hour” films, in 2004 and 2005 but reportedly dumped him because she felt disrespected when instead of attending one of her matches he chose to go to a New York party thrown by P. Diddy.

2 GRIGOR DIMITROV

The rivalry on court between Serena and fellow tennis superstar Maria Sharapova spilled off court too in 2015 when Maria started dating Serena’s ex, Bulgarian tennis player Grigor Dimitrov. After he moved onto her blonde rival, Serena reportedly said Dimitrov had a “black heart.” Serena has won every one of her matches against Maria since then without ever losing a set.

3 COMMON

She and the Oscar winning rapper dated on and off between 2008 and 2010 and he said on the “Meredith Viera Show” that she was the prime mover in the break up, saying, “It was kinda eventually a mutual thing but she initiated it.” The pair remain on good terms.

4 JACKIE LONG

Back in 2007 and 2008 actor Jackie was in her friends and family box at tennis matches, often holding her dog, and she was his date at the premiere of his movie “ATL.”  Around the time of their break up, Serena wrote a blog post despairing that her heart had been broken by a man she wouldn’t name who had told her he “needed space.” Jackie’s acting career never hit the heights of her tennis career.

5 DRAKE

A photo posted by Michelle C (@theonlymishever) on

She and the “Hotline Bling” singer first dated in 2012 and rekindled their romance in 2015 with a headline hitting public display of affection by kissing passionately at Sotto restaurant in Cincinnati. But Drake has been known to play the field and maybe wasn’t ready to be a one woman man. That was the view of  talk show host Wendy Williams at the time. She urged Serena to move on fast, saying, “Drake is a bit of a ladies man. If I were her. I’d consider Drake a snack instead of the main meal.”

READ MORE: 6 Jobs Ronda Rousey Could Do Next

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