Ryan Phillippe and Reese Witherspoon – 9 Years Together

Remember that time in the late 1990s when teen romance movies ruled the box office? That’s where Ryan Phillippe and Reese Witherspoon met, filming the movie “Cruel Intentions” together. Talk about blurring the lines between fiction and reality—they were playing a passionate couple on screen, and next thing you know, they’re walking red carpets together in real life.

By 1999, they were married, and soon after, they welcomed a daughter, Ava. A few years later, their son Deacon arrived, completing their family picture. Hollywood marriages, though glamorous, can be tricky. After seven years together, Ryan and Reese announced their separation.