Jennifer Aniston has received two engagement rings in her lifetime: one from Brad Pitt and another from Justin Thoreaux. Though both involved massive diamonds, they couldn’t have been more different—and, needless to say, a bit more attention has been given to the one that Pitt presented to Aniston in 1999, five years after they were first introduced by their managers. The high-profile duo (they were arguably the couple of the ‘90s and early 2000s) announced their engagement in November, on stage at a Sting concert of all places. The Fight Club actor grabbed his fiancée’s hand to show off her unique ring, which he made in partnership with Italian designer Silvia Damiani.
Composed of a series of round-cut stones encased in platinum, the spiral-style band encircled a nine-carat brilliant-cut stone; the design was allegedly meant to represent an eternity together and modeled off a similar pair of earrings Pitt had previously designed for his bride. As for the estimated value? Multiple outlets report that the actor spent a whopping $500,000 on the ring.
Pitt and Aniston tied the knot just under one year later, on July 29, 2000, with a lavish affair for 200 in Malibu, California; their nuptials featured 50,000 flowers, four bands, and a 13-minute-long fireworks display, reports People. Following the event, the Friends actress was spotted wearing an accompanying white gold wedding band with 10 small diamonds around the interior side, reports Shiels.
Impressive hardware and an over-the-top wedding, however, couldn’t keep the couple together: They split just five years later in January 2005, after affair rumors began swirling between Pitt and his Mr. and Mrs. Smith co-star, Angelina Jolie; Pitt and Aniston announced the news with a joint statement that rocked Hollywood: “We would like to announce that after seven years together we have decided to formally separate. For those who follow these sorts of things, we would like to explain that our separation is not the result of any of the speculation reported by the tabloid media. This decision is the result of much thoughtful consideration. We happily remain committed and caring friends with great love and admiration for one another. We ask in advance for your kindness and sensitivity in the coming months.”
In the aftermath of the duo’s split, the public had a lot of questions—all of which primarily revolved around what caused the pair’s sudden uncoupling. Another common query? What did Aniston do with the engagement ring Pitt gave her? Did she keep it? Give it back to her ex-husband? Sell it, store it, or give it away? Though the actress never opened up about the fate of the spiral diamond (and no sales or auctions were ever reported), we wouldn’t be surprised if she parted with her wedding band: It caused quite the headache for the pair in the early 2000s, after they sued its designer for capitalizing on Aniston's fame to drive sales on knock-off iterations sold in California and Las Vegas, reports International The News.
As mentioned, the fate of Aniston’s engagement ring from Brad Pitt remains a mystery; she could easily have kept it as a memento of the pair's partnership (they have seemed friendlier in recent years!) but she also could have returned it to the actor at the time of their divorce. The bauble did, however, cause a stir when the actress was spotted wearing a very similar design at the 2020 Screen Actors Guild Awards while chatting with her ex-husband, sparking rumors that she’d kept the ring all along (and that the duo was destined for reconciliation), notes The Mirror. Those rumors, however, were later debunked and hopes for the return of the it-couple of an era definitively died down (especially when Aniston affirmed that she did not want to marry again in 2022).