1. Before his family became a household name, Rob dated Playboy model Kara Monaco.
2. His first high profile relationship was with Adrienne Bailon, who famously got his name tatted and recently removed.
3. Rob dated Angela Simmons for a while back in 2010.
4. In 2011, he dated video model Rosa Acosta, who claimed to have gotten pregnant by the reality star.
5. In 2012, Rob went on a date with Rihanna, which included go-karting and clubbing.
6. Rob got cozy with model Naza Jafarian in 2013.
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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