118. Reese Witherspoon and Ryan Phillippe
Movie: Cruel Intentions
Location: New York City, New York
Year: 1999
Reese Witherspoon and Ryan Phillippe seem like ancient history now, when it comes to Hollywood relationships. The pair met on the set of Cruel Intentions, and they began dating in 1999. They were married until 2008, calling it quits after it was revealed that Phillippe had an affair with Abbie Cornish, his co-star in Stop Loss.
The two later discussed their marriage, blaming the split partially on the fact that they were both very young at the time. Witherspoon is now in her forties, and she is married to Jim Toth, to whom she’s been linked since 2011.
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