Courteney Cox and Michael Keaton
They spent almost 6 years together until they decided to part ways in July 1995. “It’s the most important relationship I’ve ever had, and I think he’s the most wonderful person I’ve ever met,” Courteney Cox said just a few months after the breakup. In fact, a ring on the actress’ hand had raised rumors about an engagement, but she later clarified that the piece of jewelry was actually her grandmother’s.