Mickey Rourke & Anastassija Makarenko (34 years)
There was a time when Micky Rourke was one of the most sought after, leading men in Hollywood, thanks to his incredibly good looks and smooth charm. But, after many years out of the limelight and in the boxing ring where Rourke would compete, both his looks and his charm were gone. However, Micky still had enough swagger to land a very young, beautiful woman Anastassija Makarenko, some three decades younger than the “Pope from Greenwich Village” actor. The two would remain a couple for six years before they split, leaving Rourke as a bachelor ever since.