Reese Witherspoon enjoyed a whirlwind romance with Ryan Phillippe.
The acting duo met at Reece's 21st birthday party back in 1997, right before work started on Cruel Intentions. Their relationship snowballed and they were married by 1999, with things coming crumbling down in 2006 when they announced their split.
But during their seven years married, with the divorce finalising in 2008, they welcomed two children, daughter Ava Phillippe in 1999 and son Deacon in 2003. Looking back on the happier times, Ryan recently took to Instagram to share an unearthed throwback.
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Ryan shared the archived image on his Instagram (Instagram/Matt Baron/BEI/Shutterstock)
The couple tied the knot all the way back in 1999 (WireImage)"We were hot and drenched in late 90s angst," he wrote of his ex-wife in the Story upload, sharing a snap from the Legally Blonde premiere. "Such a cooler time than today," he added as he tagged in his former flame Reese's account in the re-share.
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Reese didn't appear to share the image herself or interact with Ryan's post. The star-studded pair got engaged in 1998, one year after meeting – tying the knot in June 1999. They married in Charleston, South Carolina, at Old Wide Awake Plantation, a few weeks after the Cruel Intentions release. They welcomed eldest Ava in September that year.
They were open with fans about rocky moments throughout their relationship, with Ryan famously revealing they were in couple's therapy in 2002. At that time, Reece told PEOPLE: "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," she said after Ryan's confession in the New York Daily News that August.
Things appeared to be going well after that, welcoming their son in October 2003. But only three years later, in October 2006, they announced their split. "We are saddened to announce that Reese and Ryan have decided to formally separate," they said.
"They remain committed to their family and we ask that you please respect their privacy and the safety of their children at this time," the couple wrote in a statement, with Ryan later admitting that the divorce was "the darkest, saddest place I've ever been".
After their separation, they both moved on, with Reese dating Jim Toth in 2010, marrying in 2011 and welcoming son Tennessee the next year. The couple divorced in 2023. Ryan has had several relationships since Reese, but never got remarried. He reportedly shares a child with former flame Alexis Knapp welcomed in July 2022, per PEOPLE.
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