Jennifer Aniston's Engagement Rings: Brad Pitt, Justin Theroux

Double the bling! Jennifer Aniston was previously married to actors Brad Pitt and Justin Theroux and received two gorgeous engagement rings during her past romances. Although those relationships didn’t work out, the Friends actress doesn’t see them as failures.

“My marriages, they’ve been very successful, in [my] personal opinion,” the Morning Show star told Elle magazine in 2018. “And when they came to an end, it was a choice that was made because we chose to be happy. And sometimes happiness didn’t exist within that arrangement anymore.”

The Murder Mystery actress began dating Brad in 1998, and they wed in 2000. Being the biggest couple in Hollywood at the time, fans were shocked when they separated in 2005. Their split came amid rumors the Fight Club actor cheated with his Mr. & Mrs. Smith costar Angelina Jolie, whom he started seeing shortly after.

“Jen is an incredibly giving, loving and hilarious woman who remains my friend. It is an important relationship I value greatly,” Brad said during an interview with Parade in 2011, where he said he spent the ‘90s “hiding out” from the world. “The point I was trying to make is not that Jen was dull, but that I was becoming dull to myself — and that, I am responsible for.”

Brad and Angelina announced their split in 2016 and share kids Maddox, Pax, Zahara, Shiloh, Knox and Vivienne.

The Horrible Bosses actress was introduced to Justin in 2007 while on the set of Tropic Thunder by the film’s director and star, Ben Stiller. However, they didn’t become romantically involved until 2010 after they filmed Wanderlust. Jen and Justin got engaged in 2012 and tied the knot three years later. They announced their “mutual and lovingly made” decision to separate in February 2018.

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Jennifer noted during her interview with Elle that she would never stay in a relationship to avoid being single. “This is our one life and I would not stay in a situation out of fear,” she explained. “Fear of being alone. Fear of not being able to survive. To stay in a marriage based on fear feels like you’re doing your one life a disservice. When the work has been put in and it doesn’t seem that there’s an option of it working, that’s OK. That’s not a failure.”

“It’s a glass-half-full kind of thing. Always being open. Allowing myself to feel what I feel,” the Dumplin actress said of her life. “What brings me happiness? I have a great job. I have a great family. I have great friends. I have no reason to feel otherwise.”

While Jen’s future is looking bright, take a look back at her dazzling engagement rings!

Justin Theroux

The Spy Who Dumped Me actor gave Jen a dazzling eight-carat, emerald-cut ring when he popped the question in 2012.
“It’s a rock, I know,” the actress joked to the New York Times following her engagement announcement. “He rocked it up. It took me a while to get used to it. I’m not a diamond girl.”