Saddest: Ryan Phillippe/Reese Witherspoon
Another surprising split was this adorable blond pair who broke up in 2006. To the public they seemed young, pretty, and happy. When they announced their split, rumors began that Ryan was jealous of Reese’s success or that he had cheated on her with a co-star. What makes it the saddest? Their two gorgeous little blond children.
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