Ryan Phillippe and Reese Witherspoon Did Not Meet on the Set of Cruel Intentions

Credit: @reesewitherspoon

When Cruel Intentions came out in 1999, fans were excited. Ryan Phillippe and Reese Witherspoon together? They were the biggest couple of the 90s, and everyone thought they met on the set of Cruel Intentions. He played the dark and dangerous Sebastian. She played the sweet, demure Annette Hargrove. Where Sebastian was experienced beyond his teenage years, she was a proud virgin who didn’t want to give herself away until marriage. He made it his mission to seduce her, but she was not to be seduced. Their love story evolved, however, and it was very much a tragic ending for every character in this movie. However, it might shock fans to know this is not the movie that brought Ryan Phillippe and Reese Witherspoon together.

When Did Reese Witherspoon Meet Ryan Phillippe?

If these two did not meet on the set of this movie, then when did they meet? It turns out their meeting came long before the movie was made, and they were already an item when they were cast. In fact, they were already engaged when the movie was released – though fans did think they met on the set and became engaged while filming before the movie was sent into theaters. However, Reese Witherspoon said she met her future husband and the father of her two oldest children at her own birthday party.

“I don’t know what came over me – maybe the seven Midori sours – but I told him, ‘I think you’re my birthday present. He thought it was so flattering, and now that I think about it…how embarrassing!” she said of meeting him for the first time at her own 21st birthday party. It was her big night, though, and she saw something she wanted. She made it happen, and she got what she wanted out of it, so we don’t see how it’s embarrassing.

Credit: @reesewitherspoon

Their Engagement Was A Quick One

When you know, you know, right? She knew, and so did Ryan Phillippe. The Cruel Intentions costars were engaged to be married before their movie came out. They got engaged in 1998, and they were filming the movie the same year. She didn’t want to take a role in this movie. She thought her fiancé was perfect for the role of Sebastian, but she was less sure that Annette was a good fit for her. Everyone else loved her, though, and they talked her into it. Not without her sitting down and helping create a better Annette, however. She’s always been a go-getter, and she really did make this happen.

They Married Right After Cruel Intentions Was Released

It was 1999, and the movie came out in March. This couple wed only a few months later, in June. No one knew it at the time, but she was already pregnant with their daughter. Her name is Ava. The newly married celebrity couple welcomed their daughter on September 9, 1999. Her mother was 23 at the time, and Ryan Phillippe turned 25 the day after his daughter was born. Ryan Phillippe and Reese Witherspoon got married in Charleston, South Carolina, but they also remarkably kept their marriage as private as possible.

Welcoming Their Second Child and the End of Their Marriage

Following the birth of Ava, who is her mother’s twin born 23 years later, this couple had a second child. Their son, Deacon, was born four years later, in October of 2003. Almost three years to the day after their son was born, they announced their separation. The couple didn’t argue much over spousal support despite the fact they did not sign a prenup prior to their marriage. However, Witherspoon did ask the judge not to grant Philippe spousal support. He didn’t ask for it, though. He asked for joint custody of their children.

Credit: @reesewitherspoon

What Happened to This Couple?

Neither party has addressed this on a specific basis. What they do address, however, is that they are co-parents and friends. While there were rumors of infidelity on his part (he was reportedly seeing actress Abbie Cornish while still married to his wife), neither said a word about it. What they do agree on, however, is the fact that they were too young when they got married. They agreed on the fact that they were super young, they became parents very young, and they were in their 20s already married with two kids while also working the same career path. It was not an easy task for either of them, and things did not work out. Both agree that they wouldn’t change anything. They have two amazing kids as a result of their marriage, and that is all they care about.

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