Who Gave Jennifer Aniston the More Expensive Engagement Ring — Brad Pitt or Justin Theroux?

Jennifer Aniston has been a part of plenty of celebrity romances over the years, but the Friends star has only been married twice. Aniston tied the knot with Brad Pitt in 2000 in a union that lasted five years. Her second marriage came in 2015 when she exchanged vows with Justin Theroux. With Aniston enjoying the single life once again, who gave her the more expensive engagement ring — Pitt or Theroux?

Brad Pitt Jennifer Aniston
Brad Pitt and Jennifer Aniston | Kevin Winter/Getty Images

A look at Brad Pitt’s engagement ring

In the fall of 1999, Pitt and Aniston announced their engagement to the world during a Sting concert. The news came only a few months after the pair made their relationship official with their first public outing.

The couple tied the knot in the summer of 2000 in a gorgeous ceremony in Malibu. Over 200 guests watched the pair exchange vows, and the wedding featured four bands, fireworks, and 50,000 flowers.

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When it comes to Aniston’s first engagement ring, Pitt reportedly spent $500,000 on the rock, which he helped design. The Fight Club star wanted the diamonds to represent a heart and liked the symbolism of eternity.

The stunning ring features a round center stone surrounding by a spiral of smaller diamonds. Designer Silvia Damiani helped Pitt come up with the design.

Justin Theroux pops the question to Jennifer Aniston

While Pitt’s engagement ring is hard to beat, Theroux proposed to Aniston with a ring that easily rivaled it. According to Fashionista, both of the rings are valued at $500,000, but Theroux’s engagement ring was clearly bigger.

Aniston first showed off the massive rock when she was filming We’re the Millers in New Mexico. Theroux came down to visit Aniston on the set of the movie and cameras caught her wearing the ring.

Fans immediately reacted to the news and began to compare Theroux’s engagement ring to the one Pitt bought Anniston in 1999. Many fans agreed that Pitt’s ring was prettier and more unique but Theroux’s was definitely larger.

Theroux and Aniston’s marriage only lasted a few years. The couple parted ways in 2017 and Aniston has yet to start another serious relationship (though there have been plenty of rumors that she and Pitt have reignited things).

What happened to Aniston’s engagement ring?

Given how Aniston’s second engagement ring cost half a million dollars, fans have speculated about what happened to it following the divorce. We cannot say for sure what Aniston did with the ring, but Brides reports that she was not legally required to give it back.

“The engagement ring pre-dates the marriage, and therefore is Jennifer’s separate property regardless of whether it is mentioned in the prenuptial agreement,” David Glass, a lawyer based out of Los Angeles, explained.

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Glass added that once people tie the knot, the engagement ring will always stay with the recipient unless they voluntarily give it back. This is why some celebrities, like Mariah Carey, continued to wear their engagement rings even after divorcing their partners.

Aniston could have kept the engagement ring, though she has not been spotted wearing it since the breakup. The actress previously revealed that she is not a big fan of diamonds, so it is possible that she gave it back.

Jennifer Aniston rocks a familiar looking ring

Speaking of Aniston’s current lineup of rings, the actress was spotted wearing a diamond ring at the Golden Globes back in January. According to The Sun, the ring looked very similar to the one Pitt gave her in 1999, much to the delight of fans.

Cartier made the ring Aniston rocked during her red carpet appearance and it featured an Art Deco style. Although there are clear differences between the rings, they bore enough resemblance to raise a few eyebrows.

After divorcing Aniston in 2005, Pitt went on to date Angelina Jolie. The couple shares six children and tied the knot in 2014. Their marriage, however, only lasted two years before Jolie filed for divorce in the fall of 2016.

Brad Pitt and Jennifer Aniston have not addressed the rumors surrounding their friendship but there is little doubt that fans would love to see them get back together.