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Jennifer Aniston and Brad Pitt were one of Hollywood’s hottest couples in their heyday. The two started dating in the late 1990s and it wasn’t long before Pitt stunned Aniston with a $500,000 engagement ring. Although their love story did not stand the test of time, did Aniston keep her engagement ring following their divorce in 2005?

Jennifer Aniston Brad Pitt
Jennifer Aniston and Brad Pitt | Gregg DeGuire/WireImage

Inside Brad Pitt and Jennifer Aniston’s romance

Pitt and Aniston started dating sometime in 1998 after their managers introduced them. The two immediately clicked but kept their relationship out of the spotlight. According to Fame 10, Aniston would later say that they were both “really proud” of the fact that they kept their romance a secret.

“We had so much fun falling in love,” Aniston shared. “It was so private; we kept it to ourselves for so long. It was something we were really proud of.”

The pair made their engagement official during a Sting concert. Pitt and Aniston joined the musicians on stage to sing a duet about getting hitched in Las Vegas. The Friends star then showed off her massive engagement ring to the crowd.

Pitt and Aniston tied the knot in July of 2000 in a beautiful ceremony in Malibu. They invited over 200 people to the ceremony, which featured four bands, fireworks, a gospel choir, and some 50,000 flowers.

Although their marriage seemed perfect from the outside, Pitt and Aniston ultimately called it quits in 2005. Pitt went on to date and wed Angelina Jolie while Aniston tied the knot with Justin Theroux in 2015.

How much did Pitt spend on Aniston’s ring?

Pitt had a hand in designing Aniston’s ring. The Fight Club star worked with designer Silvia Damiani to craft the ring, which was based on a pair of earrings Pitt had previously purchased. As a side note, Pitt would later sue Damiani because the company was selling replicas of Aniston’s ring when they agreed it was to remain an exclusive piece.

Pitt reportedly spent $500,000 on the engagement ring, a hefty sum for 1999. Coincidentally, this is the same amount that Theroux spent on Aniston’s engagement ring over a decade later.

Aniston’s first engagement ring, meanwhile, featured a large center stone surrounded by a spiral of smaller diamonds. It is hard to say how many carats made up the ring, but we do know that Theroux’s ring was around 12 to 18 carats in total, so it was likely in that ballpark.

Considering how much Pitt spent on the ring, fans have long wondered what happened to it following the couple’s divorce in 2005. After all, a ring that is worth half a million dollars is not something that was likely left out of the divorce agreement.

Did Jennifer Aniston keep her engagement ring from Brad Pitt?

Aniston has never revealed what she did with Pitt’s engagement ring. Given how the two separated on good terms and the fact that Pitt is not going broke anytime soon, it is very likely that she kept the ring.

We can also confirm that Aniston liked the style of her first engagement ring. During the actress’s appearance on the red cart at this year’s Golden Globes, she rocked a giant sparkler that looked very similar to Pitt’s ring.

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The appearance immediately drew comparisons to Aniston’s old engagement ring, something that fans of the couple absolutely loved.

Fans have been hoping that Pitt and Aniston get back together following their respective divorces. Pitt separated from Jolie in 2016 while Aniston and Theroux called it quits in 2017.

It is unclear if Pitt and Aniston are still single. Brad Pitt has joked about his romantic life on several occasions and been spotted with Alia Shawkat, while Jennifer Aniston was recently linked to Will Speck.