Shia LaBeouf: Summer 2007
Rihanna got in touch with Transformers star Shia LaBeouf back in summer 2007, and the two met up — because if RiRi asks you out, you go. "It never got beyond one date," Shia revealed to Playboy (via MTV) two years after their outing. "The spark wasn't there. We weren't passionate about each other in that way, so we remain friends."