Ryan Phillippe has some pretty famous relationships, from his marriage to ex-wife Reese Witherspoon to a rumored fling with Rihanna.

The I Know What You Did Last Summer star was married to Witherspoon from 1999 until 2006, after meeting on the set of Cruel Intentions in 1997. Witherspoon and Phillippe share a daughter, Ava, born in 1999, and a son, Deacon, born in 2003.