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How Reese Witherspoon and Ryan Phillippe Went From Hollywood Sweethearts to Feuding Co-Parents

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These days, Reese Witherspoon and Ryan Phillippe rarely see eye to eye, despite having two grownup kids as a reminder of their love story.

Reese Witherspoon and Ryan Phillippe used to be the “It” couple envied by many until the divorce came calling. Even after their split, they remained dedicated to co-parenting their two children, Ava and Deacon Phillippe.

In October 2022, their youngest son, Deacon Phillippe, clocked nineteen, with both his parents taking to their respective social media pages to pay him birthday tributes. Meanwhile, their daughter, Ava Phillippe, is a 23-year-old college student, already forging her own path.

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Reese Witherspoon and Ryan Phillippe | Image: Pinterest
Image: Pinterest

With their kids reaching adulthood, Witherspoon and Phillippe barely have reasons to get involved in each other’s lives or maintain a civil relationship.

In fact, an insider once claimed the actress was distancing herself from her ex-husband’s messy life and saw no need to be buddies. But Phillippe believes their strife began long before they ever separated.

The actor once claimed the media used to try to pit him and his ex-wife against each other during their marriage. Such assertions were evident in the widespread insinuations that Phillippe envied his then-wife’s success.

Whether or not that was the case, it doesn’t erase the fact that these days, there is no love lost between the former lovebirds. So how did Rese Witherspoon and Ryan Phillippe go from longtime sweethearts to a distant pair barely holding on to their kids?

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Reese Witherspoon And Ryan Phillippe: The Beginning

Ryan Phillippe and Reese Witherspoon’s love story began in March 1997, after the two met at the actress’ 21st birthday bash. The “Little Fires Everywhere” star recalled walking up to him and saying, “I think you’re my birthday present,” something she now deems embarrassing.

Notwithstanding, it sparked a certain connection between them, and they began dating. Two years later, the duo united in the 1999 movie, “Cruel Intentions,” solidifying their romance.

A then-23-year-old Reese Witherspoon exchanged vows with Ryan Phillippe in June of that year, welcoming her daughter Ava three months later. Their son Deacon Phillippe arrived in October 2003.

Trouble In Paradise?

Their relationship gained public attention for the wrong reasons after Ryan Phillippe addressed the pay disparities between him and then-wife Reese Witherspoon at the 74th Academy Awards.

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At the time, the actress asked her husband if she could read out the winner, to which he famously responded:

“You make more than I do. Go ahead.”

Witherspoon would address those lines two decades later, admitting they threw her off at the time. She also claimed the lines were unscripted, and he never told her he planned to say them beforehand.

Ryan Phillippe Reese Witherspoon | Image: Pinterest
Image: Pinterest

It set the grounds for the public’s perception of Phillippe as a bitter man jealous of his wife’s success. This left many questioning how the actress was fairing in her seemingly “toxic” marriage.

Well, since the couple welcomed their son a year later, it couldn’t have been so bad, right? After all, she did thank him for his continued love and support during her 2006 Oscars acceptance speech.

The Fall Of The Witherspoon-Phillippe Romance Empire

In November 2006, eight months after singing odes to Ryan Phillippe at the Oscars, Reese Witherspoon filed for divorce, citing irreconcilable differences.

The announcement followed claims that the “Stop Loss” actor cheated on his wife with co-star Abbie Cornish. Although he publicly denied the claims, their marriage seemed to be beyond saving.

The duo announced their separation in October via a representative, who claimed they remained committed to their family. But their actions proved otherwise.

In their divorce documents, the actress requested physical custody of their two children and visitation for their dad. Phillippe, in response, requested joint legal and physical custody of the two kids, which the court granted in 2007.

Additionally, he failed to request spousal support for his ex-wife despite not signing a prenuptial agreement before their marriage.

Speaking on their failed marriage in 2015, Phillippe divulged that age was a factor as they married too young. According to him, such factors could create issues for couples in the industry as it had so much noise associated with it.

Witherspoon reiterated his claims in her own separate interview on November 2017, saying:

“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, but I’ve said to my daughter, I think, you know, at 25, you start to know yourself a little bit better.”

Where Reese Witherspoon And Ryan Phillippe Stand Today

Soon after divorcing Witherspoon, Phillippe rebounded with actress Abbie Cornish. They split in February 2010, and the actress’ rep confirmed the breakup publicly.

In response, the actor announced his decision never to date anyone with a publicist again to avoid having his relationship woes dumped on the media.

Reese also moved on to actor Jake Gyllenhaal, but theirs, too, ended. Phillippe admitted in an interview that his ex-wife reached out to him after he split from Cornish, and he did the same after her breakup with Gyllenhaal.

Then in March 2011, Witherspoon married Jim Toth and welcomed her third child. Their son, Tennessee James Toth, who remains Witherspoon’s youngest, arrived in 2012.

Phillippe affirmed his happiness over his ex-wife’s successful love life. However, following her 2013 arrest for misconduct for interfering with police after Toth got busted for DUI, a source claimed her ex-husband did not care what she did with her life.

Coincidentally, Reese got her chance to serve back those words in November 2022 amid Phillipe’s drama with ex-girlfriend Elsie Hewitt. A source claimed:

“Reese still sees Ryan’s life as messy, and she doesn’t want to be drawn into it. She doesn’t care for him – or see the need to be buddies.”

The remark came after Hewitt called Reese to testify against Philippe after accusing him of physical assault, requesting a $1 million settlement.

Interestingly, Witherspoon has been open about enduring an abusive relationship in the past. While she never named her abuser, Hewitt’s latest allegations against the “Setup” star seem to point the fingers at him.

Good to know they each forged ahead in their journeys separately, especially Witherspoon, who finally found lasting love and peace after her past chaotic love life.

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