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. After his split from Adrienne, Rob was linked to porn star Lisa Ann, who revealed, "Rob treats me like his little teacher and we have a fun sexual relationship that is simple and carefree. He brings out the total cougar in me and I just like to teach him things."
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4. Rob dated Angela Simmons for a while back in 2010.
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5. From 2011-2012, Rob had a secret relationship with Rita Ora. So secret that the world didn't know until he called her out on social media for cheating with "over 20 guys."
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6. In 2011, he dated video model Rosa Acosta, who claimed to have gotten pregnant by the reality star.
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7. In 2012, Rob went on a date with Rihanna, which included go-karting and clubbing.
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8. Rob got cozy with model Naza Jafarian in 2013.
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9. 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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Continue reading Rob Kardashian’s Relationships Over The Years