Brad Pitt Reportedly Paid A Pretty Penny For Jennifer Aniston's Engagement Ring

In 1998, future A-list couple Brad Pitt and Jennifer Aniston went on their first date. They two got engaged a year later.  Aniston first showed off the ring at a Sting concert at the Beacon Theater in Manhattan in November 1999. The ring reportedly cost $500,000, per Brides. But there was a lot of meaning behind that hefty price tag. At the center of the engagement ring Pitt created with Italian jewelry designer Silvia Damiani was a nine-carat brilliant-cut diamond. The center piece was surrounded by smaller, round diamonds clustered in a spiral shape that were encased in platinum. Pitt intended for the ring to represent eternity and wanted it to match a pair of earrings he previously designed for her.

At their wedding in Malibu in July 2000, Aniston reportedly wore a white-gold wedding band that featured 10 small diamonds in the interior. Per ABC News, Pitt's was also made of white gold and diamonds. The pair of rings were engraved with each other's first names and the year 2000. No outlets were able to confirm what Aniston did with either ring when the relationship ended. After Pitt and Aniston's pricey divorce settlement, it'd be unsurprising if they are forgotten in a drawer somewhere.

Brad Pitt and Jennifer Aniston's July 2000 wedding was coveted and well protected. The celebration for the "Friends" star and the "Fight Club'" actor took place on a Malibu estate for a guest list of 200. Aniston wore a floor-length, beaded, halter neck gown by Lawrence Steele, while Pitt looked dapper in a suit designed by former Saint Laurent creative director Hedi Slimane. Pitt and Aniston's wedding photo aged a lot better than their marriage. 

As for their vows, they were loving and specific. Aniston promised to always make Pitt's "favorite banana milkshake." And the reception featured a fireworks display, performances by Billy Preston and Melissa Etheridge, a caviar wall, a lobster dinner, and 50,000 total flowers.

Of course, the fairytale ended about five years later in part because of Pitt's rumored relationship with his now-ex-wife Angelina Jolie. But Aniston held her head high. Although in a 2005 interview with Vanity Fair she said that Pitt appeared to have "a sensitivity chip missing." Though overall her comments about her ex were kind. "I love Brad; I really love him. I will love him for the rest of my life. He's a fantastic man. I don't regret any of it, and I'm not going to beat myself up about it," the "Good Girl" star said. She called her relationship with Pitt beautiful and complicated and said they taught each other a lot about fun and healing.