When Rihanna, 28, dated Chris Brown, 27, from 2008-2009, she might’ve thought it would last forever — until, of course, he assaulted her before the 2009 Grammy Awards. Obviously, they broke up, but she eventually took him back and they started dating again at the end of 2012. They still weren’t able to make things work, though, and eventually ended things by May 2013.
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But when she wasn’t with her most serious well-known boyfriend, she’s been with many other familiar faces. Most notably, of course, is Drake, 29, who she always seems to come back to when she’s single. The two have been linked plenty of times over the last several years, and even though they’re not shy about flaunting PDA, they just never seem to take things to the next level in their relationship.
Drake & Rihanna’s PDA — PICS
Her first serious relationship after the first Chris Brown breakup, though, was with baseball player Matt Kemp in 2011, which lasted a few months. She was also linked to Travis Scott in 2015 before reigniting things with Drizzy, but again, it didn’t seem to go much further than a months-long fling.
Then, of course, there’s the singer’s rumored romance with Leonardo DiCaprio. Although they’ve denied any and all relationship reports vehemently, they’ve been seen out together on a number of different occasions, and, I mean…what are we supposed to think?!
Click through the gallery above to check out all of RiRi’s men — that we know about, at least. Hey, we can’t blame the girl for having fun with many different men while she’s still young, right?!
HollywoodLifers, who do you think Rihanna will end up with? Are you surprised she hasn’t been able to commit to any of these guys?