BROOKE SHIELDS AND ANDRE AGASSI – 2 YEARS

The thing about Hollywood relationships is that many are under some form of pressure early on. This is especially true for people who are of a particular degree of fame, such as Brooke Shields and Andre Agassi. The couple first met in 1993, after they were introduced by Lydie Benson, a mutual friend of the two. Fun fact: the two used to send “lengthy, heartfelt” faxes to each other in the beginning. We think that could be likened to sending flirty text messages today, right?

From there, a relationship bloomed between the two. Despite their seemingly harmonious union, there had been red flags early on. They had very different likes and dislikes, life views, and just nature in general. They married in 1997 and split up in 1999, about a week before their wedding anniversary. Fortunately, despite the not-so-pleasant experience, each found love anew.