Reese Witherspoon and Ryan Philippe
These “Cruel Intentions” co-stars definitely didn’t have a cruel divorce. Reese and Ryan, mom and dad to kids Eva and Deacon, separated in 2006 and were officially divorced by the next year. Despite their split, the pair is often spotted chatting amicably at their kids’ sporting events. In 2012, Witherspoon welcomed a baby boy with her second husband, Hollywood agent Jim Toth. —XFINITY Entertainment Staff (Photo by Evan Agostini/Getty Images)
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