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Reese Witherspoon & Ryan Phillippe
After meeting on "Cruel Intentions," these two were married for eight years before divorcing. They have a daughter, Ava, and son, Deacon, together. They are both repeat offenders, with Witherspoon dating her "Rendition" co-star Jake Gyllenhaal (and then they broke up), while Phillippe was seeing Australian actress Abbie Cornish, whom he met on "Stop-Loss." She was supposedly the "other woman" who wrecked his marriage.