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December 2010 - February 2011Back when Ryan Phillippe was linked with Amanda Seyfried, he was rumored to also have a short fling (hookup) with Rihanna.Sources said they'd been "very casual" and "discreet," but had been hooking up for a few months since December 2011.
March 2012 - March 2012Chris Brown and Rihanna were rumored to be rekindling their romance in early 2012.
They tweeted to each other and joined forces musically, but there was never any concrete evidence of a romantic relationship.
After dating a bevy of beauties, the Oscar-nominee has maintained a pattern of going after supermodels.
Now, he’s decided to make bikini babe, Kelly Rohrbach, 24, his latest conquest.
October 2011 - October 2011In October 2011, Rihanna reportedly began seeing Dudley O'Shaughnessy, a 21-year-old Olympic hopeful turned model.
She met the good looking guy on the set of her "We Found Love" music video.
Fans have been rooting for a Rihanna and Drake love connection forever now and it looks like it's actually happening. She's been at his side through most of his European tour over the last while.TMZ's sleuthy sources say they've turned the intense flirtation up a notch and are actually dating. While it might come as a shock to some (like Chris Brown fans), there have been some signs over the last few weeks that something was brewing. Insiders say she's been with him every single night since she arrived overseas. TMZ's sources say the Canadian star has been "in the best mood he's been in a long time."4. This might be totally unrelated, but we have noticed that Rihanna's Instagram feed has signifcantly mellowed in the last few weeks.And that's saying a lot for someone who loves to party like that gal.2. The sweet gesture was even captured on video last week. There hasn't been a butt shot since her birthday about a month ago. (Either that or she hasn't gotten a new bikini in a while.)5. Even back before they were dating, they looked like this on the stage. When Chris Brown and Rihanna got together back in 2008, it seemed like a match made in pop music heaven.Sadly, a year into the relationship came Brown's now infamous scandal.Three years after their tumultuous and violent break-up, it looks like these two are getting back together.