2. Gwyneth Paltrow
Of course, in typical Brad Pitt fashion, he met ex-girlfriend Gwyneth Paltrow during the filming of Seven. Paltrow was only 22 years old at the time while Pitt was 32 (clearly he likes younger women). The two had an extremely high profile relationship that lasted about three years. We think that this was one of Brad Pitts best matches both physically and popularity wise. The relationship started in 1994 and Pitt even proposed to the gorgeous actress!
Paltrow opened up about the very public relationship on The Howard Stern Show, saying: “I definitely fell in love with him. He was so gorgeous and sweet. I wasn’t ready, and he was too good for me.”
The two are still friends today, but who knows now that they are both single maybe they will find each other once again. Both Pitt and Paltrow went off to have incredibly big careers, so we are sure they have run into one another on more than one red carpet event.
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