The Daily Grind Video

1. Before his family became a household name, Rob dated Playboy model Kara Monaco.

Rob Kardashian Source:Getty

2. His first high profile relationship was with Adrienne Bailon, who famously got his name tatted and recently removed.

Rob Kardashian Source:Getty

3. Rob dated Angela Simmons for a while back in 2010.

Rob kardashian Source:Getty

4. In 2011, he dated video model Rosa Acosta, who claimed to have gotten pregnant by the reality star.

Red Star Access Presents G.O.O.D. Music Event In Houston Hosted By Rosa Acosta Featuring Cyhi The Prynce And Pusha T Source:Getty

5. In 2012, Rob went on a date with Rihanna, which included go-karting and clubbing.

Rihanna Source:Getty

6. Rob got cozy with model Naza Jafarian in 2013.

Rob Kardashian 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.

Karrueche Source:Getty