A serial cougar, this hopeless romantic chanteuse and her boy toy (18 years younger!) snapped out of it after just two years together, though they remain friends. Cher is currently dating writer/director Ron Zimmerman (whom she met on Facebook… whaaat?). Though her new beau is 12 years her junior, he’s the first man over 30 that she’s ever dated. At 65, that’s pretty impressive. Go, girl!