Reese Witherspoon and Ryan Phillippe
The couple met through a mutual friend and two years later after costarring in 1999's Cruel Intentions, Ryan proposed.
Marriage followed and kids Ava, and son Deacon soon after.
But like all couples, the two had their share of problems and in 2002, Phillippe told New York's Daily News that they were in couples therapy.
That didn't seem to work either leading the Walk the Line actress to file for divorce citing irreconcilable differences.
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