Though short-lived, one of Cruise's most notable romances was with none other than music icon Cher. The two connected for the first time at the 1985 wedding of Madonna and Sean Penn, though they got to know one another better at a White House event, per People. "Then a bunch of people who were dyslexic were invited to the White House, and Tom and I are both dyslexic . . . there was definitely a connection," she explained to the outlet.
Though it is unknown exactly how long Cruise and Cher's rendezvous lasted, the "Believe" singer did tell Andy Cohen on "Watch What Happens Live With Andy Cohen" in 2013 that their romance "was pretty hot and heavy for a little minute," and that Cruise was easily in her top five list of lovers.
