Ryan Phillippe & Reese Witherspoon

When the 1999 cult classic Cruel Intentions first came out in the cinemas, fans of Ryan Phillippe and Reese Witherspoon could not help but gush at the couple who got engaged after a year of dating at the time. It so happened that on that very same year, the two sealed the deal and had a June wedding. A little over three months later, the couple welcomed their first daughter Ava into the world. Four years later, their son, Deacon, was born. The 90s love team first met at the Legally Blonde actress’s 21st birthday in 1997. The moment their eyes locked, the undeniable chemistry and attraction flowed like electricity.

However, after seven years of marriage, the couple has announced that they have decided to part ways in a joint statement. Their adorable children turned into spitting images of their parents. While Ava inherited her mother’s charming smile and ocean blue eyes, Deacon, on the other hand, is a dead ringer for Ryan.