It was 1999, and Hollywood basically belonged to them. If you were breathing in the late nineties, you remember the image: Reese Witherspoon and Ryan Phillippe, glowing and gorgeous, standing as the ultimate "it" couple. They met at Reese’s 21st birthday party—she famously told him he was her birthday present after a few Midori sours—and within two years, they were married. Then came Cruel Intentions, two beautiful kids, and what looked like a rare, stable marriage in a town that eats relationships for breakfast.
Then, in 2006, it all went sideways.
When the news broke that the couple was separating, fans were genuinely floored. It wasn't just a tabloid headline; it felt like the end of an era. People have spent years asking why did ryan and reese divorce, looking for a single "smoking gun" that destroyed the dream. Honestly? The truth is a lot messier and more human than a simple tabloid scandal. It was a perfect storm of being too young, a massive career imbalance, and some very loud rumors that just wouldn't go away.
The Problem With Getting Married at 23
Ryan Phillippe hasn't been shy about this. Years later, he told Larry King that the biggest issue was simply their age. "When we got together we were so young," he said. And he was right. Reese was 23 when they tied the knot; Ryan was 24. At that age, you’re still figuring out which direction your life is headed, let alone trying to navigate a high-profile marriage while the world watches your every move.
Reese has echoed this sentiment. She’s called that time "terrifying" and "anxiety-producing." Imagine trying to grow up and raise a family while paparazzi are literally jumping on the hood of your car at church. That’s not a metaphor—Reese actually described that happening. When you're that young, you don't always have the emotional toolkit to handle that kind of external pressure plus the internal work of a marriage.
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The "Oscar Curse" and Career Friction
There is an old, somewhat sexist Hollywood superstition called the "Best Actress Curse." The idea is that once a woman wins the Oscar for Best Actress, her marriage falls apart. In 2006, Reese won the Academy Award for Walk the Line. Within months, the marriage was over.
While "curses" aren't real, the ego friction definitely is.
- Income Gap: By the time they split, Reese was pulling in $15 million to $20 million per movie. Ryan was reportedly making closer to $2 million.
- Power Dynamics: Reese was becoming a mogul; Ryan was still searching for his next big hit after Flags of Our Fathers.
- The "Mr. Witherspoon" Label: It’s tough for any actor to be overshadowed by their spouse, especially in an industry that measures worth by box office numbers and awards.
Ryan once mentioned in an interview with W Magazine that the reasons were "far more complicated and far less interesting" than people wanted them to be. He hated the narrative that he was jealous, but it’s hard to ignore the timing.
Those Persistent Abbie Cornish Rumors
We have to talk about the BlackBerry.
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Rumors exploded that Reese found "saucy" text messages on Ryan’s phone from his Stop-Loss co-star, Abbie Cornish. While Ryan has denied that an affair was the cause of the divorce—saying he had "difficulties" in his marriage long before he met Abbie—the optics weren't great. He started dating Abbie shortly after the split, and they stayed together for about three years.
For many fans, this was the definitive answer to why did ryan and reese divorce. But looking back with 2026 hindsight, it feels more like the infidelity (if it happened as reported) was a symptom of a marriage that was already on life support, rather than the primary disease.
The Scrambled Egg Years
The aftermath wasn't pretty. Reese has described the year following the divorce as a time when her brain felt like "scrambled eggs." She couldn't be creative. She was floundering.
"You can’t really be very creative when you feel like your brain is scrambled eggs. I was just kind of floundering career-wise. I wasn’t making things I was passionate about." — Reese Witherspoon to 60 Minutes.
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It took her years to find her footing again, eventually leading to her "Pacific Standard" production era and hits like Wild and Big Little Lies. For Ryan, the split led to a "dark, sad place" where he struggled to even get out of bed for months. It was a heavy, transformative loss for both of them.
Where They Are Now: The Co-Parenting Win
If there is a silver lining to the why did ryan and reese divorce story, it’s how they handled the decades that followed. Unlike many Hollywood exes who trade barbs in the press for thirty years, Ryan and Reese put in the work.
- Shared Milestones: They are regularly seen together at their kids' graduations and birthdays.
- Mutual Respect: Ryan has publicly praised Reese’s work ethic and business savvy.
- Family First: When Ryan faced legal trouble in 2019 (a lawsuit from a former girlfriend), Reese actually volunteered to testify on his behalf, stating he had never been violent with her. That’s a level of support you don't see in "bitter" divorces.
Basically, they grew up. They realized that while they weren't meant to be husband and wife, they were meant to be partners in raising Ava and Deacon.
Takeaways for the Rest of Us:
- Age Matters: Getting married in your early 20s carries a statistically higher risk, especially when combined with high-stress environments.
- Career Balance: Unequal success in a relationship requires active communication and ego-checking.
- The Long Game: A "failed" marriage doesn't have to mean a failed family.
If you're looking for more details on how they managed to stay friends, you can look into their joint appearances at their son Deacon's album launch or Ava's social media, where she frequently posts about both parents with equal love. The romance died, but the family survived.
Check out our other deep dives into celebrity relationship timelines to see how other "golden couples" managed their public splits.