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Chris Brown

From the beginning, to the domestic abuse, to the end, to the back again then the end again, we were there through it all.

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Drake

Where do we begin with these two?

It started in 2009 when the two allegedly hooked up at Lucky Strike Bowling Alley in NYC. Since then, there’s been years of denying rumors, hinting that they were dating, making songs about each other (Drake raps about their night at Lucky Strike in “Fireworks”), and denying more rumors. Then, there was that big fight that broke out between Drake and Chris Brown in an NYC club in 2012.

Drake and Rihanna perform onstage during The 53rd Annual GRAMMY Awards held at Staples Center on February 13, 2011 in Los Angeles, California.
Drake and Rihanna perform onstage during The 53rd Annual GRAMMY Awards held at Staples Center on February 13, 2011 in Los Angeles, California.

 

Matt Kemp

Immediately following her breakup with Chris Brown, Rihanna moved on to baseballer Matt Kemp. Their romance was short-lived. This was right before Rih went on a dating spree, telling Vogue, “I just let it go. I don’t ever want to have to depend on a relationship. I think it’s a really special thing to find love. It’s beautiful. Nothing can match it. But I want to make sure I find other things in life that I love — besides love.”

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Melissa Forde

J.R. Smith