Angelina Jolie vs. Jennifer Aniston: Whose Brad Pitt Engagement Ring Is Better?

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Before Brad Pitt popped the question to the mom of his six children, Angelina Jolie, he got down on one knee in front of Jennifer Aniston in 1999.

Both times, Pitt has collaborated with the jeweler designing his future fiancee's engagement ring. For Aniston's multi-level, swirl-design sparkler, he tapped Silvia Damiani; for Jolie's giant emerald-cut stone, he worked with their long-time jeweler and friend, Robert Procop.

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But it looks like Pitt, 48, has gotten a bit more conservative when it comes down to the price tag. Back in 1999, Aniston's ring, which she debuted during a Sting concert in New York, was estimated to be worth around $500,000; jewelry expert Michael O'Connor quoted Jolie's ring to be somewhere around $250,000.

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On Friday, Brangelina fans everywhere were rejoicing when Pitt's rep confirmed that the long-time loves were finally settling down and making things official. Jolie, 36, flashed her new engagement bling during a private art viewing at LACMA on Wednesday.

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But lest we forget, before Aniston and Jolie, Gwyenth Paltrow stole Pitt's heart -- he proposed to her with a diamond sparkler in early 1997 after the pair dated for three years. They called off their plans to marry in June 1997.

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