Dated: 1986

This pairing makes us wish there were a reality TV show that paired the weirdest characters in Hollywood together and sent them on dates. The Tom Cruise and Cher episode would be absolutely hilarious. First of all, there's the 16-year age gap. Second of all, there's the transparent, glittery outfit Cher would likely wear and Tom's reaction to it—probably a flash of his winning smile, the one that usually conceals all the batshit crazy ideas circling around inside. Finally, there's their conversation. Would she give him tips on how to dress to reinvent himself post-divorce? Would he try to recruit her into The Church? We've never wished for a time machine so badly.