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Ryan and Reese met at Witherspoon’s 21st birthday party in 1997, where they hit it off quickly.

The “Cruel Intentions” co-stars then got engaged in December 1998 and married in June 1999.
The pair quickly started a family with the arrival of their daughter, Ava, in September of that year. Four years later, they welcomed their son, Deacon, in October 2003.

The two split in 2006 and divorced in June 2008.