A Look Back at Ryan Phillippe and Reese Witherspoon’s Relationship

Introduction to Their Romance

Ryan Phillippe and Reese Witherspoon were one of Hollywood’s most beloved couples during the late 1990s and early 2000s. Their relationship began in a whirlwind romance that captured the hearts of fans, especially after they starred together in the iconic film Cruel Intentions (1999). The couple’s journey from young love to marriage, parenthood, and eventual separation is a fascinating tale of both passion and challenges.

Meeting and Early Relationship

The couple first met at Witherspoon’s 21st birthday party in March 1997. According to Witherspoon, she was quite taken with Phillippe, jokingly telling him, “I think you’re my birthday present.” This playful encounter marked the beginning of their relationship. They quickly became inseparable, living together for about a year before filming Cruel Intentions. Their chemistry on-screen translated into real life, leading to an engagement in 1998.

Marriage and Family Life

Witherspoon and Phillippe tied the knot on June 5, 1999, just weeks after the release of Cruel Intentions. At the time of their wedding, Witherspoon was pregnant with their first child. They welcomed their daughter Ava on September 9, 1999. Four years later, they had a son named Deacon on October 23, 2003. As new parents navigating Hollywood fame, they often spoke about the challenges of balancing work and family life.

Public Appearances and Career Highlights

Throughout their marriage, Witherspoon and Phillippe made numerous public appearances together. Notably, they presented an award at the Oscars in 2002 where Phillippe humorously acknowledged Witherspoon’s success by saying she should read the winner’s name because “you make more than I do.” This moment highlighted not only their playful dynamic but also touched upon gender norms in Hollywood.

Witherspoon received critical acclaim for her role in Walk the Line (2005), winning an Academy Award for Best Actress. During her acceptance speech at the Oscars in March 2006, she thanked Phillippe publicly for his support. However, this period also marked significant strain in their relationship.

Separation and Divorce

In October 2006, just days after attending events together celebrating Witherspoon’s success for Walk the Line, they announced their separation. The news shocked fans as it came seemingly out of nowhere; they had appeared happy just weeks prior. In November of that year, Witherspoon filed for divorce citing irreconcilable differences.

Rumors swirled around their split with allegations of infidelity involving Phillippe and his co-star Abbie Cornish. In interviews following their separation, both actors expressed deep sadness over the end of their marriage but emphasized their commitment to co-parenting Ava and Deacon.

Co-Parenting Success

Despite their divorce being finalized in July 2008, Witherspoon and Phillippe have maintained a positive co-parenting relationship over the years. They have been seen together at various family events such as birthdays and graduations for Ava and Deacon. Both have spoken highly of each other post-divorce; Phillippe has stated that it is crucial for divorced parents to maintain a connection for the sake of their children.

In recent years, both actors have moved on romantically—Witherspoon married Jim Toth in March 2011 (though they announced their divorce in March 2023), while Phillippe has been linked to several partners since his split from Witherspoon.

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