Discover Brad Pitt’s proposal and the value of the rings he gave to Angelina Jolie and Jennifer Aniston

Brad Pitt’s proposals were big news in Hollywood, be it his first time presenting the ring to Jennifer Aniston and the second time to Angelina Jolie.

Jennifer Aniston and Brad Pitt met in 1998 through their managers, and they immediately hit it off. Their relationship was highly publicized and they were once the it couple of Hollywood. Pitt was racing to the top with exceptional roles, while Aniston was at the peak of her fame with her role in FRIENDS. However, things didn’t last long between them.

Angelina Jolie and Pitt’s relationship had alleged overlaps with his marriage to Aniston. It is widely believed that it was the affair with Jolie that ended Pitt and Aniston’s marriage. After Pitt divorced Aniston, the Mr. & Mrs. Smith stars started dating and married in 2014. Two years later, the marriage ended after Jolie filed for divorce.

Jennifer Aniston and Brad Pitt were married after two years of dating

Jennifer Aniston and Brad Pitt in a still from FRIENDS | Credits: NBC

Jennifer Aniston got her first engagement ring from Brad Pitt in 1999. They had been dating for only more than a year, but they were so madly in love. The news of the proposal got so much attention because Aniston and Pitt announced it during a Sting concert.

In November 1999, they attended a Sting concert where they got on stage. Pitt took Aniston’s hand and showed off her brand-new ring, with a massive nine-carat diamond at the center of it. It was made in partnership with Italian designer Silvia Damiani. The design was supposed to represent an eternity together (via Brides).

According to multiple reports, the ring cost $500,000. They tied the knot a year later in July 2000. It was a grand wedding with 200 people in attendance in Malibu, California. While they were initially considered one of the most loving couples in Hollywood, they announced their separation in January 2005.

The fate of the engagement ring remains unknown, but Aniston caused quite a stir in 2020 at the SAG Awards when she wore a similar design. Fans speculated that she had kept the ring all along, and even rumors started flying that the couple was headed for a reconciliation (via The Mirror).

Angelina Jolie got a ring from Brad Pitt in front of their children

Angelina Jolie and Brad Pitt in Mr. & Mrs. Smith | Credits: 20th Century Studios
Angelina Jolie and Brad Pitt waited a long time before Pitt decided to pop the question. Their fling reportedly began on the set of Mr. & Mrs. Smith. When they began dating, Jolie was already divorced twice, from Jonny Lee Miller and Billy Bob Thornton.
When it came to the proposal, Pitt and Jolie always wanted it to happen in front of their children. The proposal happened in April 2012, which was later confirmed by Pitt’s manager. It was reported that Pitt gathered their children before presenting Jolie the ring box.

According to Perez Hilton, the ring cost $500,000 and had a diamond at its center (via UsWeekly). A source shared with Perez Hilton about the proposal, “Angelina cried and smiled. Everyone hugged once she put on. She went around and showed it to each of the kids” (via Woman’s Day).

Pitt once shared that their kids—Maddox, Pax, Zahara, Shiloh, and twins Knox and Vivienne—were increasingly desperate to see them tie the knot. He shared with THR about getting married to Jolie:

We’d actually like to, and it seems to mean more and more to our kids. We made this declaration some time ago that we weren’t going to do it till everyone can. But I don’t think we’ll be able to hold out. It means so much to my kids, and they ask a lot. And it means something to me, too, to make that kind of commitment.

The couple got married in 2014 at the Chateau Miraval in a French ceremony. Prior to that, they had a small wedding in California where they obtained their marriage license.