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Follow us on Facebook: www.facebook.com Follow us on Twitter: twitter.com Brad Pitt proposed to Angelina Jolie with a giant emerald-cut stone. It is estimated to cost $250000! But back in 1999, Brad Pitt got down on one knee in front of Jennifer Aniston, and her engagement ring was estimated to be worth around a whopping $500000. Perhaps Brad is a bit more frugal this time around. After all, before he ever proposed to Angie or Jen, he had already given an engagement ring to Gwyneth Paltrow too! He popped the question to her in 1997 after three years of dating. But they called off their wedding.