Things You Didn’t Know About Reese Witherspoon And Ryan Phillippe’s Relationship

During their nine years together, it really felt as though Reese Witherspoon and Ryan Phillippe were the perfect couple. With their all-American good looks and their stellar Hollywood careers, it really felt like they came straight out of a fairy tale. Unfortunately, like most Hollywood couples that get together when they’re really young, these two didn’t last, which left all of us with broken hearts. Thankfully, we can still remember what it was like when they were together, which is why we have 11 things you didn’t know about the former couple’s relationship:

11. The Best Birthday Present

They met at Reese’s 21st birthday party. Ryan came with a mutual friend of theirs. According to her, she went up to him and told him that she thought he was her birthday present. They clicked immediately and began a long distance correspondence, communicating via phone calls, letters and emails because he was filming I Know What You Did Last Summer in North Carolina. Five weeks after their first meeting, she went to visit him on set. After filming wrapped, they took a road trip together and fell in love.

10. Opposites Attract

Reese and Ryan were total opposites in many ways, but it worked for them. “It was a pretty intense, emotional connection that happened between Reese and me,” he told The Morning Call back in 1999. “There’s a definite balance there. Reese is a happy, light-hearted person, but she’s also incredibly intelligent. I tend to be considerably darker. She keeps me from getting too dark and depressed and that’s essential in a business that’s based on uncertainty and insecurity.”

9. Becoming Domesticated

When they first began living together, neither one of them knew how to cook or how to use the stove and oven, so they had to learn. “We were helpless in the kitchen and after a while it got ridiculous ordering out for food or going to restaurants every night. I wound up buying a lot of cookbooks and we studied them for weeks and weeks until we chose our own set of favourite recipes. We also talked to our moms about how to operate an oven and basic things like that,” Reese told

8. Surprise Pregnancy

Reese and Ryan’s first child, Ava, was totally unplanned. While Ryan wasn’t nervous about parenthood, Reese was because she had absolutely no experience with children prior to her becoming a mother. “Ava wasn’t planned and suddenly I was faced with the prospect of becoming a mother and I had never even held a newborn in my arms before! What was interesting about our becoming parents was that Ryan was the really cool one. His mother had once run a day-care centre and he could change a diaper in something like five seconds flat. It was amazing to see him work! I feel like I went through a crash course in motherhood,” she said.

Myung Jung Kim

Myung Jung Kim

7. Wedding

They got engaged in December 1998 and were married in June 1999 in Charleston, South Carolina at the Old Wide Awake Plantation. Witherspoon was five months pregnant at the time with their daughter Ava. Four years after welcoming Ava into the world, the couple had their second child, Deacon. Reese had found out that she was pregnant while they were on vacation in the Caribbean.

6. Jealousy

In 2002, Witherspoon and Phillippe were presenting together at the Oscars when he made a joke that she should announce the winner because she made more money than him. Many were left wondering if there was some jealousy in the relationship. While Phillippe was arguably the bigger star during the ‘90s, after the success of Legally Blonde, Witherspoon became more famous and she started commanding a much larger paycheck than her husband.

5. Marriage Counseling

The Walk the Line actress talked openly about going to marriage counseling to keep her relationship with her husband on track. “Sure we’ve had counseling. But it’s healthy to deal with problems that come up when you’re living with another human being and forging your lives together,” she said “We see our marriage not as a free ride but as a partnership you work on. You need to discuss things and be open about how to make each other feel gold and happy.” She added, “Love is a beautiful thing but you’ve got to nurture it through the 50 things that come during the day, like driving the kids to school, who’s picking up the in-laws from the airport and working when one of your kids is running a high fever. Those are the normal things that stress every couple.”

4. Formal Separation

In October 2006, they announced that they had formally separated. Rumor has it that they broke up before Flags of Our Father premiere where they were caught having an argument by a paparazzo. A month after announcing that they had separated, the Sweet Home Alabama star filed for divorce, citing irreconcilable differences.

3. No Prenup

Shortly after Ryan and Reese had split, it came out that the couple didn’t get a prenup when they got married. At that point in their marriage, the Just Like Heaven actress was commanding $20 million a film while the Flags of Our Father actor was commanding only $2.5 million a film. Under California law, Ryan was entitled to 50% of Reese’s earnings during their marriage. In the end, he didn’t ask for spousal support or child support and instead asked for joint custody of their two children, Ava and Deacon.

2. Cheating Rumors

When news broke that Witherspoon and Phillippe were done, it came out that the I Know What You Did Last Summer actor had gotten a little too close to his co-star on the set of the 2006 film Stop Loss. Around the time that the A-list couple announced their separation, sources came forward claiming that they saw him and Abbie Cornish kissing at a Japanese restaurant while he was still married. Phillippe denied that he and Cornish were anything more than co-stars; however, two years after his split from Witherspoon, he went public with his relationship with his former co-star.

1. Post Split

Reese and Ryan both handled the split differently. According to Ryan, he had trouble getting out of bed for the first four or five months while Reese found the divorce to be humiliating. However, in spite of how traumatic the breakup was for them, they have remained civil and committed to raising their children. “My ex-husband is very involved in raising our beautiful children. We’re very lucky because we both grew up in working families in middle America. We’re on the same page that way,” she said. “When we’re with our children, we’re very good about checking ourselves. I’m teaching the children what we were taught growing up – a real set of rules, discipline and love.”

Photo by Broadimage / Rex Features

Photo by Broadimage / Rex Features



Cate has a B.A. and an M.A. in English Literature and has been the Managing Editor of Fame10 for more than 6 years. Despite having a love for the works of Thomas Hardy, Leo Tolstoy and Lord Byron, she also has an intense fascination with pop culture. When she isn’t writing for Fame10, she’s planning her next big adventure in Southeast Asia.