Real-Life Celebrity Breakup: Reese Witherspoon and Ryan Phillippe

Reese Witherspoon and Ryan Phillippe haven’t been together in many years, but their relationship was the stuff of 90s fans’ dreams. Not only were both actors in very successful movies, but they were also a major A-list couple for quite a few years.

In fact, Witherspoon went from being a teen actress to an Oscar-winner all in the span of their relationship. From how the couple first met to their sad split, find out more about this once great celebrity romance.

How Did Reese Witherspoon and Ryan Phillippe Meet?

Witherspoon and Phillippe met in 1997 at her 21st birthday party. Phillippe came with a mutual friend and Witherspoon supposedly went up to him and told him she thought he was her birthday present. They had an immediate connection and began a long-distance relationship because Phillippe was away shooting I Knew What You Did Last Summer.

Party Like It’s 1999
Phillippe and Witherspoon got engaged in December 1998 while the couple was vacationing at The Planter’s Inn in Charleston, South Carolina. They tied the knot in June 1999 in Charleston, South Carolina. Witherspoon was actually five months pregnant at the time with their daughter, Ava.

Cruel Intentions
After meeting and falling in love, Witherspoon and Phillippe were both cast in the drama, Cruel Intentions, which also starred Sarah Michelle Gellar and Selma Blair. The movie premiered three months before the couple tied the knot and was a commercial success.

Family of Four

The couple had their daughter, Ava (who was named after Phillippe’s grandmother), on September 9, 1999. They then welcomed their second child, son Deacon (named after former Pittsburgh Pirates pitcher Deacon Phillippe, a distant relative of Ryan’s), in October 2003.

Parting Ways
Phillippe and Witherspoon announced their separation in October 2006 following rumors their relationship was on the rocks. Then, one month after they separated, the actress officially filed for divorce. Both have said that getting married so young contributed to the end of their relationship.