Years down, the two are now married with two daughters. Of all the men Aniston dated, Brad Pitt, whom she married from 2000 to 2005 remains the most popular.
She has gone on after the marriage collapsed to date others including John Mayer and Justin Theroux.
Diaz would go ahead to meet Benji Madden whom she would end up marrying. In 1999, J-Lo married her waiter boyfriend Ojani Noa, who was five years younger than the singer. Her marriage to Ben Affleck was called off shortly before it began.
While the couple was popular, the age difference between the two was three years.
Age may as well be nothing more than numbers, especially among female celebs who dated, married, or are currently dating younger men at the moment.
It is quite obvious how much notorious male celebrities have become in marrying women far much younger.
J-lo went on to have a relationship with dancer Casper Smart, who was 17 years her junior.