Back in the late '90s, Reese Witherspoon and Ryan Phillippe were one of Hollywood's biggest It couples. The two first met at Reese's 21st birthday party in March 1997 and became engaged a year later. Aside from showing sweet PDA on the red carpet, they also took their love to the big screen by playing love interests in Cruel Intentions in 1999. That June, they tied the knot at a plantation in South Carolina. While they eventually got divorced in 2007, the former couple has remained good friends as they coparent their two children, Ava and Deacon. If you're feeling a little nostalgic, you'll definitely get a kick out of these throwback photos of the couple.