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Reese Witherspoon and Ryan Phillippe, Cruel Intentions

  • The onscreen love story: Dastardly Sebastian is only courting the virginal Annette for sport, until he starts to fall for her for real. When Annette finds that he's just using her to win a bet, she ditches him. Not wanting to lose her, Sebastian puts his evil side on the back burner and proves his love.
  • The offscreen love story: Phillippe and Witherspoon had already met when they started filming this movie, and they got married just after its 1999 release. But after two kids and seven years of marriage, they split.

Image Source: Everett Collection