You’d struggle to find a celebrity duo who defined the late ’90s more than Reese Witherspoon and Ryan Phillippe.
The former couple, who met in 1997 and tied the knot in 1999, may not have lasted in the marriage department, but their decade-long romance is still talked about even to this day.
Many fans incorrectly assume Witherspoon and Phillippe met and fell in love on the set of their 1999 film Cruel Intentions. You could be forgiven for thinking this – but the pair had actually been together for years already.
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For a long time, it seemed the Hollywood pair were unbreakable and hopelessly in love. But it wasn’t meant to be.
After a seven-year marriage and nearly 10 years together, in 2006, Witherspoon and Philippe announced their marriage was over. They shared two children – Ava and Deacon – and vowed to remain “committed” to their family.
But what actually happened and where did it all go wrong?
How did Reese Witherspoon and Ryan Phillippe meet?
Witherspoon and Philippe first met in 1997 at the Legally Blonde star’s 21st birthday party.
For the actress, it was almost love at first sight. “I don’t know what came over me – maybe the seven Midori sours – but I told [Ryan], ‘I think you’re my birthday present,'” she told Jane magazine in 1998.
“He thought it was so flattering, and now that I think about it … how embarrassing!”
The public didn’t know much about their secret Hollywood romance until Cruel Intentions eventually hit theatres in 1999.
The film starred Witherspoon alongside her boyfriend Philippe, with Sarah Michelle Gellar and Selma Blair also landing roles in the cult film.
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How long were Reese Witherspoon and Ryan Phillippe together?
That same year, Witherspoon and Phillippe tied the knot in South Carolina. It was less than 12 months after he popped the question.
In September 1999, the couple welcomed their first child – a daughter named Ava. She arrived three months after their wedding.
A few years later in 2002, the pair raised eyebrows and whispers of tension behind the scenes began after an on-stage exchange at the 74th Academy Awards.
The couple were presenting on stage when Phillippe made a joke about how much his wife earned.
“You make more than I do. Go ahead,” the actor said after Witherspoon asked to read the winner’s name out loud.
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Years later, Witherspoon would admit she was blindsided by her then-husband’s joke.
“I forgot that ever happened. He did say that, and no, it wasn’t scripted. He didn’t tell me he was going to say that before it happened on air,” she said on the HFPA in Conversation podcast.
A year later, in 2003, the couple welcomed their second child, a son named Deacon.
By 2006, it seemed Phillippe and Witherspoon were still going strong when the actress thanked her husband during her Oscar acceptance speech.
She had just won Best Actress for her role as June Carter Cash in Walk the Line.
“I want to say thank you to my wonderful husband and my two children, who should be going to bed,” she said. “And thank you for loving me so much and supporting me.”
Why did Reese Witherspoon and Ryan Phillippe break up?
In October that year, however, it all came crashing down. The couple shocked fans when they announced their shock separation in a joint statement.
“We are saddened to announce that Reese and Ryan have decided to formally separate,” a rep for the couple said at the time.
“They remain committed to their family and we ask that you please respect their privacy and the safety of their children at this time.”
Witherspoon filed for divorce in November 2006, citing “irreconcilable differences”.
Neither of the stars spoke publicly about the reason behind their split, however rumours flew that Phillippe had an alleged affair with his Stop-Loss co-star, Abbie Cornish.
Reports blamed Cornish for the breakdown of his marriage with Witherspoon, however the actor denied he’d ever been unfaithful to his ex-wife.
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Phillippe and the Australian actress began dating shortly after the split announcement, however they called it quits after four years together.
He later spoke about their split during an interview on Howard Stern. “I have a new rule: not to date anyone who has a publicist. Who announces a breakup? I don’t understand that!,” he said.
“There’s no need for that. I’ve been dumped on in the press for relationship stuff since Reese and I divorced. I’m tired of getting s—t on. I don’t feel like I deserve it.
“Things happen! How many people have you broken up with over your life?”
Who is Ryan Phillippe dating now?
After splitting from Cornish, Phillippe went on to date actress Alexis Knapp in 2010. The pair later split, then Knapp welcomed the couple’s daughter Kai in 2011.
He has also been linked to Nikki Reed, Amanda Seyfried, Rihanna and Demi Lovato. As of 2024, Phillippe appears to be single.
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Who is Reese Witherspoon dating now?
Witherspoon married her second husband, actor and producer Jim Toth, in 2011.
The couple welcomed a son, Tennessee, in 2012.
In 2023, Witherspoon took to Instagram on to announce she was splitting from Toth, just days before they were due to celebrate their 12-year anniversary.
“We have some personal news to share…” their joint statement began.
“It is with a great deal of care and consideration that we have made the difficult decision to divorce.
“We have enjoyed so many wonderful years together and are moving forward with deep love, kindness and mutual respect for everything we have created together.”
Are Reese Witherspoon and Ryan Phillippe still friends?
Witherspoon and her ex-husband Phillippe remain on good terms.
The two actors were recently reunited while celebrating their son’s career milestone.
Witherspoon and Phillippe attended their 19-year-old son Deacon Phillippe’s release party for his album A New Earth.
The proud father took to Instagram to share snaps of the celebration, posting one image of the Legally Blonde actress smiling alongside their two children Deacon and Ava Phillippe, 23.
“Awesome night w family & friends celebrating the release of, ‘A New Earth’ by @deaconphillippe !!” Ryan captioned a carousel of images from the gathering.
“Stream, download, and listen to the album.”
The photos led to fans egg on a reconciliation between the two actors.
With Witherspoon now single after ending her 12-year marriage to Jim Toth, speculation was at an all-time high.
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