Dating: George Clooney
Age difference: 18 years
This one makes us grin every time we see it. George Clooney, handsomest and smoothest man on the planet, walks down the red carpet of all his swanky events with a lady wrestler on his arm. For all her hotness, the fact remains that she used to brawl with women for the amusement of the rabble. He is a Hollywood leading man in the tradition of Cary Grant and Spencer Tracy; she is good at the corner foot choke and the hair-pull snapmare.