Why did Reese Witherspoon and Ryan Phillippe break up?

Reese Witherspoon and Ryan Phillippe were one of the most talked-about couples of the noughties, with their relationship spanning from 1997 to 2006.

During their nine-year relationship, Reese and Ryan became household names - both individually in their acting careers, and as a Hollywood couple, marrying in 1999 and welcoming two children, Ava (now 23) and Deacon (now 19) during their relationship. 

Despite the former couple parting ways 17 years ago, the Cruel Intentions co-stars are still part of each other's lives, working as dedicated co-parents to their two children. And following a series of social media reunions, showing the pair celebrating their children's birthdays and their son Deacon's graduation, Reese Witherspoon and Ryan Phillippe's former relationship is still making news. 

Reese Witherspoon and Ryan Phillippe

Contrary to popular belief, Reese Witherspoon and Ryan Phillippe did not meet on the set of Cruel Intentions, the 1999 romantic drama of which they both star. 

In fact, they actually met two years earlier, with their iconic 1997 "meet cute" supposedly taking place at Witherspoon's 21st birthday party. 

“I don't know what came over me — maybe the seven Midori sours — but I told Ryan, 'I think you're my birthday present,'” the actress told Jane Magazine of their meeting the following year. “He thought it was so flattering, and now that I think about it, how embarrassing!"

And so started the epic romance that was Reese Witherspoon and Ryan Phillippe - complete with matching noughties fashion, romantic drama co-starring and Oscar wins.

They were engaged 12 months later, tying the knot in 1999 just three months after the cinema release of Cruel Intentions. Reese Witherspoon was six months pregnant at the time, with the former couple welcoming their first child, Ava, three months after their South Carolina wedding. Four years later, they announced the birth of their son, Deacon.

"I was so, so young, I was, like, ridiculously young," Witherspoon recalled of their relationship in a 2011 interview with ELLE. "I learnt a lot, though. It was an excellent opportunity for me to really find out what it means to be a partner and to be in a marriage and it’s not anything that I thought it was. You can’t say, 'I don’t want to talk about that'. You just can’t. You’ve got to talk about it all."

Why did Reese Witherspoon and Ryan Phillippe break up?

Reese Witherspoon and Ryan Phillippe announced their split in October 2006 after seven years of marriage, with Witherspoon filing for divorce, citing irreconcilable differences.

“We are saddened to announce that Reese and Ryan have decided to formally separate,” a representative for the former couple announced. “They remain committed to their family and we ask that you please respect their privacy and the safety of their children at this time.”

"Phew, that was a tough year that followed. I got divorced the next year and I spent a few years just trying to feel better," Witherspoon explained in an interview with CBS' 60 minutes. "You can't really be very creative when you feel like your brain is scrambled eggs. I was just kind of floundering career-wise. I wasn't making things I was passionate about ... And it was really clear that audiences weren't responding to anything I was putting out there."

The couple's separation was followed by rumours of infidelity, with Phillippe accused of cheating on Witherspoon with Abbie Cornish his co-star from 2008 war film, Stop-Loss. He has denied these rumours.

“I’m not a perfect person, but I’m not guilty of a lot of the things I have been accused of," Phillippe announced in a statement in November 2006. "My priority is and always has been the health and safety of my family."

In the years since, both Witherspoon and Phillippe have opened up about the break up, citing their young age as the main reason behind the separation. Witherspoon and Phillippe were 23 and 35, respectively, when they got married.

"When we got together we were so young," Phillippe recalled in an interview with Larry King. "I think it can create issues with two people in this industry because there's so much noise that goes along with it."

Witherspoon appeared to agree in a later interview on ITV show Lorraine, explaining: "I got married when I was 23 and I had two kids by the time I was 27. So, I think, I don't know. Sometimes it's good to know yourself. I would never change anything [but] I said to my daughter, [at] 25 you start to know yourself a little bit better."

"It is so important as divorced parents to keep that connection," Phillippe said of their divorce and now co-parenting in a 2010 interview on The Ellen Show. "It makes the kids feel better that the parents are interacting. We go to all the school events together, and we're there for each other.

"We've done a really good job with that, and our kids are happy and healthy and doing awesome."

We will continue to update this story.