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HomeGeneralInside Reese Witherspoon and Ryan Phillippe's Relationship Timeline

Inside Reese Witherspoon and Ryan Phillippe’s Relationship Timeline

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Here’s a look at Reese Witherspoon and Ryan Phillippe’s relationship timeline from their time as a power couple in the 90s.

Like most love stories, Reese Witherspoon and Ryan Phillipe’s romantic relationship started unexpectedly for both actors. In the 90s, the lovebirds were one of Hollywood’s most famous couples. During an interview with Jane Magazine in 1998, Witherspoon explained how their romance started.

Reese Witherspoon and Ryan Phillippe's relationship
Image: Pinterest

Although many people believed that Witherspoon and Phillippe first connected on the set of “Cruel Intentions,” which was ne of the movies that raised their profile as partners and movie stars, the two had been secretly dating for a while before they even began the film. Witherspoon claimed in the interview that they met at her 21st birthday party, which was love at first sight for her. She told the publication:

“I don’t know what got into me, maybe the seven Midori sours, but I told him, “I suppose you’re my birthday present.” When I stop to think about it, how embarrassing! He thought it was so flattering!

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However, that encounter kickstarted their romance, and it didn’t take long before they got engaged. After their engagement, the duo starred opposite each other in their hit movie “Cruel Intentions.” Also, their undeniable chemistry on the screen was one of the things that made the film successful. 

Getting Married and Starting a Family

Reese Witherspoon and Ryan Phillippe's relationship
Image: Pinterest

Just weeks after the release of “Cruel Intentions,” in June 1999, the young celebrities took a significant step in their romance. Witherspoon and Phillippe tied the knot in Charleston, South Carolina, in a breathtaking romantic ceremony. The wedding ceremony held at the Old Wide Awake Plantation, and by that time, Witherspoon was already heavily pregnant. 

Three months after getting married, the lovebirds welcomed their first child together, a daughter, Ava. At the time, Witherspoon, 23, and Phillippe, 25, couldn’t contain their joy in adding to their family. Meanwhile, during an appearance on “The Drew Barrymore Show,” Witherspoon revealed how she felt about being a young mother. The actress explained she was terrified when she got pregnant at 22 because she didn’t know how to balance work and motherhood.  Witherspoon noted that at that period, she was just like every other parent trying to figure things out. 

Witherspoon and Phillippe Went Through Couple’s Therapy

Reese Witherspoon and Ryan Phillippe
Image: Pinterest

After the birth of their child, Witherspoon and Phillippe’s relationship was off the news for a while, bar their Oscars appearance in March 2002. However, just months later, Phillippe’s comments during an interview with the New York Daily News raised some eyebrows when he disclosed they were attending couple’s therapy. According to the actor, they were trying to work on their relationship because not doing that might make their marriage fall apart. 

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Meanwhile, Witherspoon also echoed his comments during her interview with PEOPLE, where she noted that they were having problems just like normal couples. She explained:

“I’m not interested in the fallacy of the Hollywood relationship: ‘We have perfect children who never cry; we never have problems; we never argue, we’re always best friends.’ That’s just not true. We’re normal people with normal problems.”

However, it looked like the duo’s relationship was working out again when the couple announced the birth of their second child in October 2003. Witherspoon and Phillippe added their son Deacon to their expanding family. However, shortly after that, things turned worse for the duo.

Witherspoon and Phillippe Announced Their Separation

Three years after welcoming their son, Witherspoon and Phillippe decided to end their seven-year relationship. The news shocked most people who knew the couple because they showed no signs of relationship problems before the announcement. In a joint statement released by their representative, the couple expressed their sadness at the decision. However, they also remained committed to their family and work. 

In October 2006, divorce papers were submitted to the Los Angeles Superior Court, and they were formally finalized one year later. Witherspoon asked for shared custody of their two children in the court documents and demanded that Philippe be given sole visitation rights without receiving spousal support.

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The Couple Spoke on Their Divorce

In an interview with W Magazine in 2008, Phillippe acknowledged that the divorce was his most challenging and depressing moment. He claimed, “I couldn’t get out of bed for a good four or five months.” However, although coming to terms with the divorce was hard for him, the actor stayed positive. Even though it was a challenging process for him, he got less depressed about it every day.

Meanwhile, Witherspoon also spoke candidly about her divorce from Phillippe in an interview with “CBS’ 60 Minutes.” The actress talked about how challenging the situation was and how it nearly cost her a promising career. Witherspoon explained that for a few years, all she did was try to feel better. The actress noted:

“Simply put, I was having career trouble. I wasn’t producing stuff I was enthusiastic about. Additionally, it was abundantly evident that the audience weren’t responding to anything I was saying. When your brain feels like it’s made of scrambled eggs, you can’t really be very creative.”

Witherspoon and Phillippe Have Moved On

In 2011, Witherspoon tied the knot for a second time when she married Jim Toth in a private ceremony at her California ranch. Afterward, Phillippe revealed he was happy for his ex-wife and wished her the best. Also, because of their co-parenting arrangement, Witherspoon and Phillippe remain connected to one another despite their separation.

In June 2022, the ex-couple were spotted together celebrating their son Deacon’s graduation from high school. The ex-couple also posed together with their son, and Witherspoon uploaded the image on her Instagram page. She also lauded Deacon for how proud he made them feel. 

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