1. Before his family became a household name, Rob dated Playboy model Kara Monaco.
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2. His first high profile relationship was with Adrienne Bailon, who famously got his name tatted and recently removed.
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3. Rob dated Angela Simmons for a while back in 2010.
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4. In 2011, he dated video model Rosa Acosta, who claimed to have gotten pregnant by the reality star.
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5. In 2012, Rob went on a date with Rihanna, which included go-karting and clubbing.
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6. Rob got cozy with model Naza Jafarian in 2013.
Source:Splash News
7. Most recently, Rob was rumored to be dating Chris Brown’s ex Karrueche. He posted a photo of their text conversation, then deleted it.
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