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Ryan Phillippe and Reese Witherspoon were once one of Hollywood’s star couples. Their relationship went the distance for several years before they would divorce in 2008. But initially, Phillippe recalled having a difficult time with the split. So much so the star admitted he stopped taking care of himself because of it.

How did Ryan Phillipe and Reese Witherspoon first meet?

Reese Witherspoon smiling with Ryan Phillippe.
Ryan Phillippe and Reese Witherspoon | S. Granitz/WireImage

According to US Magazine, Reese Witherspoon first met Ryan Phillipe at her 21st birthday party in 1997. Witherspoon ended up making the first move, teasing Phillipe with a line she would find embarrassing years later.

“I don’t know what came over me. Maybe the seven Midori sours – but I told [Ryan], ‘I think you’re my birthday present,’” Witherspoon told Jane Magazine. “He thought it was so flattering, and now that I think about it…how embarrassing!”

Witherspoon and Phillipe would tie the knot with each other in 1999. But their marriage wouldn’t last, and in 2006, the couple put out a joint statement announcing their breakup.

“We are saddened to announce that Reese and Ryan have decided to formally separate,” a rep said on behalf of the two. “They remain committed to their family and we ask that you please respect their privacy and the safety of their children at this time.”

Ryan Phillippe was a ‘physical wreck’ after his break-up with Reese Witherspoon

It was difficult for both Phillippe and Witherspoon to move on after the split. Phillippe shared how the end of his marriage took the actor to some particularly dark places. It not only impacted him emotionally, but physically as well.

“After the divorce I wanted to die,” Phillippe once told Man About Town (via Daily Mail). “I was ready to kill myself. I was not taking care of myself at all. I would wake up and cry and vomit.”

Witherspoon also confided in an interview with 60 Minutes the divorce’s effect on her.

“That was a tough year that followed,” Witherspoon confided. “I got divorced next year, and I spent a few years just trying to feel better. Y’know, you can’t really be very creative when you feel like your brain is scrambled eggs.”

This would take a bit of a toll on the Legally Blonde star’s career, who found herself going through the motions.

“And then I was kind of floundering career-wise because I wasn’t making things I was passionate about, I was just kind of working,” she said.

Reese Witherspoon didn’t regret marrying Ryan Phillippe


How Old Was Reese Witherspoon in ‘Legally Blonde’?

Although many things can cause the end of a marriage, Phillippe believes that their youth played a huge part in their own split.

“I think more of a problem was age,” Phillippe once told Larry King. “We got together so young.”

Phillippe later confided that the two at least were able to remain friends over the years.

Despite how things might have ended up between the two, Witherspoon didn’t have any regrets about marrying her Cruel Intentions co-star.

“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,” Witherspoon said to Lorraine. “I would never change anything. I’ve said to my daughter, I think, you know, 25, you start to know yourself a little bit better.”

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