Brad Pitt’s Engagements: From Jennifer Aniston To Angelina Jolie

MTV News goes back to 1998 to look at how the actor's engagements compare.

Last week, Brad Pitt and Angelina Jolie made headlines when they announced that after seven years and six kids together, they are getting hitched.

Before confirming Brangelina’s engagement , the twosome had frequently been speculated about, with editors cooking up cover lines that the glamorous, globe-trotting duo would marry … someday. Well, it seems that someday is still someday, since no date has been set just yet.

But before he ties the knot with Angelina, let’s go back to 1998, the year he popped the question to Jennifer Aniston. Fourteen years ago, celebrity news was a different being than it is today. Without a multitude of celebrity blogs and Twitter, it was easier for celebrities, Brad included, to fly relatively under the radar. While their wedding announcement was covered, the amount of publicity surrounding it was minute by today’s standards.

In fact, Brad and Jennifer announced their plans to wed only days before the $1 million ceremony took place that August. The twosome had denied even being engaged up until that last-minute announcement.

According to reports, he had given her a Silvia Damiani-designed ring, worth an estimated $500,000. She showed off the stunner months later in 1999 at a Sting concert, according to Usmagazine.com.

While Brad and Jen kept it hush-hush, Brangelina released a statement about their engagement, but only after their jewelry designer Robert Procop confirmed he worked with Brad on a ring. Angelina was spotted sporting the ring, worth more than $250,000, at a private museum event last week. “Yes, it’s confirmed,” Cynthia Pett-Dante said last Friday. “It is a promise for the future and their kids are very happy. There’s no date set at this time.”

Pitt had been engaged once before both these women. Even though they never walked down the aisle, he was engaged to Gwyneth Paltrow in the mid-’90s before the couple broke up in 1997. He started dating Aniston shortly after.