Reese Witherspoon & Ryan Phillippe’s Relationship, From First Love To Co-Parenting

The gorgeous stars were Hollywood's It couple until they split after seven years of marriage. Find out all about their relationship here!

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Reese Witherspoon and Ryan Phillippe may not be a hot item anymore — but they are certainly still hot Hollywood heavyweights. After playing boarding school lovers in the 1999 teen cult classic Cruel Intentions, the famous exes have gone on to carve their own enviable paths in Tinseltown. Reese took home a Best Actress Oscar in 2006 for her role as June Carter in Walk the Line, and has since produced award-winning TV shows like Big Little Lies. Ryan has become somewhat of an action star and a funnyman, as he can currently be seen in Will Forte’s MacGruber.

Reese Witherspoon
Reese Witherspoon and Ryan Phillippe were married in 1999. (Everett Collection/Shutterstock)

While still together, Reese and Ryan welcomed daughter Ava in 1999 and son Deacon in 2003. The former couple now share the title of co-parenting champs. Keep reading to find out all about the exes relationship, below!

Reese and Ryan’s meet-cute.

Two years before they lit up the silver screen with their palpable chemistry in Cruel Intentions, Reese and Ryan were first introduced during what could have been their very own rom-com meet-cute. Reese was celebrating her big 21st birthday when none other than Ryan walked through the door!

“I crashed her party,” Ryan told The Morning Call in 1999, via E! News. “I went with a friend because I knew there would be free food and drinks. I was just sitting back in the corner pounding away the drinks when somebody walked over and introduced Reese to me.”

Reese gave her own version of the meeting while speaking with Jane a year prior. “I met him at my 21st birthday party,” she recalled. “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!”

Walking down the aisle together.

Reese Witherspoon
Ryan Phillippe and Reese Witherspoon starred in 1999’s ‘Cruel Intentions.’ (Everett Collection/Shutterstock)

When Reese was 23 and Ryan was 25, the pair said “I do” in a small ceremony in Charleston, South Carolina in June 1999. Reese opened up about the decision to get married so young when she was discussing turning 40 to Today. “What do you do when you get to 40, and you made a decision when you were 25 to get married and have kids? I mean, I got married when I was 23, and I had two kids by the time I was 27. So I don’t know, you know, sometimes it’s good to know yourself. I would never change anything.”

One big happy family.

Reese was four months pregnant when she exchanged vows with Ryan. The happy couple welcomed Ava in September of 1999. “[She and Ava] are best friends,” a source told Us Weekly of Reese’s relationship with her daughter.. “They just love being together. Reese and  Ava talk several times a day and they go to each other for everything. [Ava] has learned so much by being with her mom and traveling the world with her.”

Deacon arrived four years later and was just as whole-heartedly welcomed into the fold. “Happy 18th birthday to our gorgeous, smart, talented, and caring son,” Ryan wrote about Deacon in October 2021. “You are a true light in this world and are so loved by all who know you. We are lucky to be your mom and dad.” Ryan also complimenting Reese, mentioning that he felt like they “did pretty good.”

A heartbreaking split.

Reese Witherspoon
Reese Witherspoon and Ryan Phillippe divorced in 2006. (Featureflash Photo Agency).

Reese and Ryan announced they would be going their separate ways in 2006 after seven years of marriage. While cheating rumors plagued the couple for years, with Ryan suspected of carrying on an affair with his then co-star, Abbie Cornish, the actor denied ever having stepped out on Reese. “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,” Ryan said in a statement at the time.