Inside Reese Witherspoon's Relationship With Ryan Phillippe
Olivia Jakiel
Many people think that Reese Witherspoon and Ryan Phillippe met on the set of "Cruel Intentions," but their relationship dates to Witherspoon's 21st birthday.
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The List
Reese Witherspoon has been in the spotlight ever since her breakout role in "The Man in the Moon" in 1991 (via IMDb). Since then, she's been a household name in Tinseltown, appearing in critically-acclaimed movies like "Cruel Intentions," "Pleasantville," "Sweet Home Alabama," "Walk the Line," "Wild," and "A Wrinkle in Time." Of course, she completely solidified her A-list status after bringing the iconic character of Elle Woods in "Legally Blonde" to life in 2000, and in the last five years, fans have seen Witherspoon take over the screens in their living rooms with starring roles on hit TV shows like "Big Little Lies," "Little Fires Everywhere," and "The Morning Show," which stars "Friends" alum Jennifer Aniston.

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Witherspoon is also set to appear in the upcoming "Friends: The Reunion" special on HBO Max, and fans everywhere are undoubtedly excited to see the "Hot Pursuit" actress reunite with the main cast and other guest-stars on the long-running sitcom, like Tom Selleck, as well as "Friends" super-fans like Justin Bieber, Lady Gaga, Mindy Kaling, and more (via Paper).

While many people think that Reese Witherspoon and her ex-husband, Ryan Phillippe, met on the set of "Cruel Intentions" in 1999, the pair's relationship actually dates a bit farther back — to Witherspoon's 21st birthday two years prior, to be exact. "I crashed her party," Ryan told Pennsylvania newspaper, The Morning Call, in 1999 (via E! News). "I went with a friend because I knew there would be free food and drinks. I was just sitting back in the corner pounding away the drinks when somebody walked over and introduced Reese to me."

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Witherspoon recalled their rom-com worthy meet-cute in an interview with Jane a year prior, telling the outlet, "I don't know what came over me – maybe the seven Midori sours – but I told him, 'I think you're my birthday present.' He thought it was so flattering, and now that I think about it ... how embarrassing!"

Just two years after meeting and a few months after the premiere of the couple's cult classic film, "Cruel Intentions," Witherspoon and Phillippe tied the knot in a charming ceremony in Charleston, South Carolina in June 1999.

A few short months after her and Phillippe's wedding in September 1999, Witherspoon gave birth to the couple's first child together, a daughter named Ava, who is literally the spitting image of her famous mom (via InStyle). Four years later, the couple welcomed their second child, a son named Deacon.

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"[She and Ava] are best friends," a source told Us Weekly of the mother-daughter duo's relationship in 2018. "They just love being together. Reese and Ava talk several times a day and they go to each other for everything. [Ava] has learned so much by being with her mom and traveling the world with her."

Witherspoon is also vocal about the love she has for all of her children — she also shares an 8-year-old son named Tennesee James with now-husband Jim Toth — and regularly gushes about all three on social media. And while everyone knows that motherhood isn't easy no matter who you are or what you do, Witherspoon has been open and honest about the struggles she's faced being a young mom. "I didn't know how to balance work and motherhood," she said of having her firstborn at age 23. "You just do it. ... I was just like every other mom and dad trying to figure it out. There's a lot of compromise. Every bit of that sacrifice is truly worth it."

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In 2006, the world was shocked after Witherspoon and Phillippe announced their separation just seven years after tying the knot. At the time, Phillippe was accused of cheating on Witherspoon with his "Stop-Loss" co-star, Abbie Cornish — something that he's maintained his innocence of since. "I'm not a perfect person, but I'm not guilty of a lot of the things I have been accused of. My priority is and always has been the health and safety of my family," Phillippe said in a statement at the time (via Us Weekly).

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However, Phillippe and Cornish started dating in 2006 — the same year he and Witherspoon announced their split — and while both Phillippe and Cornish have denied affair allegations throughout the years, the timing of their relationship has always been a little suspicious. In 2010, shortly after Phillippe and Cornish's relationship ended, the former '90s heartthrob defended his love life and sketchy relationship timing to longtime radio host Howard Stern, telling him (via Us Weekly), "I've been dumped on in the press for relationship stuff since Reese [Witherspoon] and I divorced. I'm tired of getting s*** on. Things happen! How many people have you broken up with over your life?"

While the world may never find out whether the couple's marriage ended because of an alleged affair or not, both Witherspoon and Phillippe have spoken openly about the demise of their marriage, and both chalked it up to one thing: They were young. "I think more of the problem was age. When we got together we were so young," Phillipe explained to the late Larry King in 2015 (via InStyle). "I think it can create issues with two people in this industry because there's so much noise that goes along with it."

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Two years later, Witherspoon echoed her ex-husband's thoughts on their marriage on ITV's "Loraine," saying, "I got married when I was 23 and I had two kids by the time I was 27. So I don't know, you know, sometimes it's good to know yourself. I would never change anything. I've said to my daughter, I think, you know, [at] 25, you start to know yourself a little bit better."

While Hollywood's former young it couple may have ended their marriage over a decade ago, it seems like there's no bad blood between the exes. Over the years, Phillippe has gushed about Witherspoon and even wished her and husband Jim Toth well when the pair got married in 2011. "I'm very happy for both Reese and Jim," he said to the New York Daily News at the time (via Us Weekly). "I wish nothing but the best for the mother of my children."

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Last year, Witherspoon and Phillippe reunited to celebrate the 17th birthday of their son, Deacon (via People). The former lovebirds took to their respective Instagram accounts to commemorate their son's big day, each penning emotional and sweet tributes and sharing a plethora of current pics and throwback photos. Phillippe even posted a video of his ex-wife bringing out a birthday cake for their son, and the video also showed their daughter, Ava, and Witherspoon's son with Toth, Tennessee, attending their brother's celebration.