Madonna & Jesus Luz
Madonna again! We had to, sorry. So, Madonna actually began dating Jesus Luz after she split from Guy Ritchie. Luz is 28 years younger than her, and they dated for two years.
Hugh Hefner & Crystal Harris
Well, is anyone really that surprised? Hugh Hefner had his fair share of relations with younger women. Perhaps it was the marriage thaat shocked people. Back on Christmas Eve in 2010, Hefner proposed to Crystal. They married at the Playboy Mansion. Oh, the age gap…60 years.