Once one of Hollywood’s most beloved couples, Reese Witherspoon and Ryan Phillippe called it quits in 2006 after seven years of marriage — but the twosome are forever linked thanks to their look-alike children.

While many believe that the twosome met and fell in love while filming the 1999 movie Cruel Intentions, Witherspoon confirmed on Watch What Happens Live With Andy Cohen in 2015 that they had been “living together for about a year and a half” when they shot the film. She also told Andy Cohen at the time that daughter Ava and son Deacon hadn’t seen the movie.

“They’re like, ‘This is so weird!’ And especially seeing me and their dad having sex. It’s so weird,” she said at the time. “Not interested.”

It wasn’t always smooth sailing for the twosome, however. When news of their split broke in 2006, Phillippe was accused of cheating on Witherspoon with Stop-Loss costar Abbie Cornish.

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

Phillippe and Cornish went on to date until February 2010. He later welcomed a daughter with then-girlfriend Alexis Knapp in 2011. Witherspoon, for her part, married talent agent Jim Toth and gave birth to son Tennessee in September 2012. Witherspoon and Toth announced in March 2023 that they were divorcing after nearly 12 years of marriage.

Scroll through for a timeline of Witherspoon and Phillippe’s ups and downs: