Brad Pitt, 56 and Angelina Jolie, 45—11 year difference

Brad Pitt, American actor and film producer, was born on December 18, 1963; Angelina Jolie, American actress, filmmaker, and humanitarian, was born on June 4, 1975, who is 12 years younger. Theirs was a love we all hoped would last. But, alas, most relationships of this kind in Hollywood don’t, which is why all credit is given to the ones that do—and the ones that do are few and far between.

After two years of marriage, they filed for divorce on September 19, 2016, for reasons that are still vague and amorphous. But they were at least able to weather all sorts of storms during their 12-year relationship. It was one of the most shocking separations at the time, not least because they had 6 wonderful children. The six children, three of whom were adopted, while the others are biological.