The duo first met in 1997, and they went on to star in the 1999 cult-favorite drama Cruel Intentions together (which debuted the same year that they got married). Their frequent red carpet appearances at award shows made the news of their separation all the more surprising.
Since their break up, Ryan and Reese have moved on with other people — Reese has been married to Jim Toth since 2011, and Ryan was engaged to Paulina Slagter (he also welcomed a daughter with Pitch Perfect star Alexis Knapp in 2011). But, that hasn't stopped fans from wanting to know what exactly happened between America's sweetheart and her fellow movie star ex.
Why did Reese and Ryan break up?
In the years since Ryan and Reese filed for divorce, both parties have sporadically made comments about what exactly led to their split.
One contributing factor that they both have agreed upon is that they were simply too young when they got married. At the time of their 1999 nuptials, Reese was just 23 years old, while her husband was 25. The couple had been together for about a year before they got engaged, and Reese was six months pregnant with daughter Ava when she said, "I Do."
In 2015, the Big Sky actor appeared on Larry King Now, and he said that their youth caused "issues."
When asked if the biggest problem was the fact that they were both in the same industry, Ryan said no.
"I think more of the problem was age, when we got together so young," he said. "I think it can create issues — two people in this industry — because there's so much noise that goes along with it."
He then shared that he was friends with his ex.
Reese echoed this sentiment regarding age as a factor as well.
While appearing on the ITV talk series Lorraine in 2017, Reese said that she took on a lot of adult responsibilities at an early age. She also shared that she didn't really know who she was until she was 25, at which point, she was a married mom of two.
"I mean, I got married when I was 23," Reese explained on the show. "I had two kids by the time I was 27... Sometimes it's good to know yourself. I would never change anything. I've said to my daughter, 'you know, 25 you start to know yourself a little bit better.'"
Another headline-making rumor regarding the divorce was alleged infidelity on Ryan's part.
When their split was first announced in 2006, there was speculation that Ryan was engaging in a relationship with his Stop-Loss co-star, Abbie Cornish.
While the affair rumors have not officially been corroborated, Ryan and Abbie did go public with their relationship following his separation from Reese in 2006. Abbie later discussed how her romance with Ryan was her first real introduction to the spotlight.
In 2009, Reese hinted at other reasons for her divorce from Ryan when she was featured on the cover of Elle. She said that the divorce was "very humiliating and very isolating."
"Blame, blame, blame. You know? And it's a really easy thing to do, and I'm certainly guilty of it. [You have to] look at yourself and go: 'What part of this do I need to own? Which part of this is my responsibility?'" she said, according to People. "And that's the painful work that you have to go through to hopefully get some real-life knowledge out of it."
By 2009, Abbie and Ryan moved in together, but they broke up in 2010.
Reese discussed her awkward 2002 Academy Awards moment with Ryan.
While appearing on the HFPA in Conversation podcast in December of 2020, Reese was reminded of a moment she shared with her ex-husband at the 2002 Academy Awards. She presented the Best Makeup award with her then-husband. As Ryan opened the envelope with the name of the winning film, Reese asked if she could read it out loud.
"You make more than I do, go ahead," Ryan responded.
On the podcast, journalist Margaret Gardiner asked Reese about whether the moment was real. She also linked it back to the power struggle in relationships when a woman makes as much or more than her husband.
"That moment, you're reminding me of that. I forgot that ever happened," Reese said on the podcast. "But you're right, he did say that, and no, it wasn't scripted, and he didn't tell me he was going to say that before it happened on air. So I was a little bit flummoxed in the moment, too."
"I don't know why he said, I don't know," she continued, before adding that it's "hard on women."
Ryan and Reese may have been able to move past the gritty details of their finalized divorce in 2008, but that doesn't mean fans have.
Those who want to remember their union will simply have to watch Cruel Intentions.