Date: 5/14/2012

Rihanna may have been less than complimentary toward J.R. during the playoffs this year, but in May of 2012, things were reportedly a bit different. Hooking up with a girl as selective as Rihanna is definitely the mark of a true badass, and from what was reported, it sounds like Smith may have actually been able to pull it off. Gossip magazine In Touch wrote last year that the two were seen being "very flirty in the club all night and holding hands. She was sitting on his lap and was really into him."

Neither of the two have ever been one to shy away from controversial behavior, so the pairing makes sense. Did Swoosh actually get it with RiRi? We certainly can't confirm it but, hey, we'd never be stupid enough to bet against a man like him.