Reese Witherspoon Reunites with Ex to Support Son after Always Being Pitted ‘against Each Other’

• Reese Witherspoon and Ryan Phillippe’s love story started much earlier than everyone thought.
• The couple separated after only seven years together, with many rumors surrounding their split.
• Recently, the exes reunited to lend support to their son.

Recently separated Reese was all smiles as she joined her ex-husband, Ryan, at their son’s album release celebration party. The duo became smitten with each other when they were both very young and merely in their early 20s.

However, their dreamy romance and lovely union came to an unexpected halt after only seven years, much to the shock and surprise of their fans. Two years after their split, the couple’s divorce was finalized.

Ryan Phillippe and Reese Witherspoon at the premiere of “Rat Race” at the Cineplex Odeon Century Plaza in Los Angeles, Ca. 7/30/01. | Source: Getty Images

When the pair officially decided to go their separate ways, their well-wishers were heartbroken, and many rumors surfaced. According to the rumor mill, Ryan cheated on his then-wife and the mother of his children with another actress. But that wasn’t all.

In an interview with Larry King in 2015, Ryan explained what went down in his relationship with Reese.

Ryan was even held responsible for being jealous of Reese’s highly successful career. Instead of keeping mum on the matter, the “54” star commented on all the rumors.

Ryan Phillippe and Reese Witherspoon at the Kodak Theatre in Hollywood, California | Source: Getty Images

The Love Story That Started Much Earlier than All Thought

On an episode of “Watch What Happens Live with Andy Cohen” in August 2018, Reese explained that she and Ryan met way before they starred in the 1999 movie “Cruel Intentions.”

She shared this information in response to Andy’s question about whether she and Ryan fell in love during the making of the classic film.

The “Legally Blonde” alum revealed that they had been living together for over a year and a half before they starred in the romantic drama movie. When a fan asked Reese if she would ever let her kids watch “Cruel Intentions,” she said they hadn’t seen the movie.

She stated that her children found seeing their parents in a reel-life love scene weird. Reese added that her kids seemed disinterested in watching her other films.

Reese Witherspoon listens as Ryan Phillippe whispers in her ear in a scene from the film ‘Cruel Intentions’, 1999. | Source: Getty Images

23-year-old Ryan met Reese at her 21st birthday celebration in 1997. It didn’t take long for the duo to connect and forge a relationship. The stars tied the knot in 1999, only weeks after “Cruel Intentions” came out.

Ryan was 25, and Reese was 23 when they married. They stayed together for seven years and welcomed two beautiful children—Ava Elizabeth Phillippe and Deacon Reese Phillippe—before separating in 2006. Their divorce proceedings were finalized in 2008.

The news of the couple’s split sent a shockwave among their fans, and multiple accusations surfaced against Ryan. The “Crash” alum was accused of cheating on Reese with one of his co-stars, Abbie Cornish, but he denied the rumors.

Nyc 10/8/98 E 339393 005 The Motion Picture Club Awards Luncheon Reese Witherspoon & Boyfriend Ryan Phillippe | Source: Getty Images

Reese and Ryan’s Divorce and the Rumors Surrounding It

In an exclusive interview with “The Guardian” in October 2022, Ryan shed more light on his relationship with his ex-wife. The “Antitrust” star expressed that he and Reese had shared some beautiful moments at the peak of their union, apart from parental bliss.

But despite their shared joys, the couple called it quits after seven years, much to the speculation of media and their followers. It was rumored, but never fully confirmed, that Ryan cheated on his then-spouse, which led to their split.

Astonishingly, subtle signs had begun to show that not everything was well for the then-lovebirds four years before they announced their separation. In 2002, the duo appeared to read out nominees for “Best Makeup” at the Oscars.

Actress Reese Witherspoon Is visited by her husband Ryan Phillippe and their child on the set of “Legally Blonde” October 21, 2000 in Los Angeles, CA. | Source: Getty Images

Reese light-heartedly asked her then-husband if she could open the envelope and declare the winner’s name. Without even a second’s delay and formulating his response without meeting Reese’s eyes, Ryan responded:

“You make more than I do. Go ahead.”

The “Wild” actress later expressed she was bewildered by Ryan’s unscripted response. While Ryan was enjoying fame during their union, Reese’s stardom was undeniably much bigger—something he said had never bothered him. Ryan shared:

“People were always trying to pit us against each other, and any time there were rumblings that we were going through a rough patch, they would make it seem like it was because I was jealous.”

Calling himself “pro-woman,” Ryan said he never felt intimidated by a woman’s success because he had been raised by one and had three sisters. But unfortunately, he noted how everyone wanted to project that image of him then and painted him in a negative light.

Reese Witherspoon, winner Best Actress in a Leading Role for “Walk the Line”, and Ryan Phillippe | Source: Getty Images

In an interview with Larry King in 2015, Ryan explained what went down in his relationship with Reese. The “Straight A’s” alum shared he and Reese were very young when they got together, and due to them being in show business, a lot of noise came along with their union.

But having overcome the odds, Ryan and Reese have forged a friendly connection. Commenting on their roles as parents, the “Chaos” star said he and his ex-spouse did a great job at co-parenting, which he knew with complete certainty even when they were young and naïve.

Ryan, who met Reese on her 21st birthday, said he knew Hollywood romances could be short-lived. But even at that time, he admitted to being sure of one thing—even if they didn’t last much longer, he saw Reese as an excellent person to raise children with.

The “Collide” actor, who said he had immense respect and admiration for his ex-wife, made a surprising confession in November 2007. He told Daily Mail UK that he wanted to die and was ready to kill himself after his divorce from Reese and had almost given up on himself.

While commenting on his infidelity rumors, Ryan told PEOPLE in November 2006 that despite not being a perfect person, he wasn’t guilty of many things he had been accused of. He also noted that he had always prioritized his family’s well-being and safety.

The Exes Reunite for Their Son, Deacon

Reese and Ryan were recently seen together to support their son, Deacon, who is building his music career. The “Water for Elephants” actress, who announced her separation from Jim Toth in March, smiled warmly as she joined Ryan at Deacon’s album release party.

The daddy-son duo took to their Instagram accounts to share heartwarming photos from the celebration. They shared a collection of pictures where Deacon had his arms hooked to his parents and older sister, Ava.

Deacon, 23, chose a black shirt and a white checkered jacket, accessorizing with a beaded necklace. Meanwhile, his 48-year-old dad donned a plain white shirt which he matched with a cozy sweater.

The budding musician also shared pictures with his 23-year-old sister and his mother. Reese chose a red plaid jacket with jeans, while Ava stunned in her green crop top and black pants. Posting photos with Reese and their kids from the Friday, April 14 celebration, Ryan wrote:

“Awesome night w family & friends celebrating the release of, ‘A New Earth’ by @deaconphillippe !! Stream, download, and listen to the album (sic).”

Despite divorcing in 2008, Reese and Ryan looked candid as they rooted for their son. Surprisingly, it wasn’t the first time the duo came together after ending their union.

Earlier, they joined forces on numerous occasions concerning their children, including birthday parties and graduation celebrations. Reese and Ryan have maintained a friendly dynamic through the years and enjoy co-parenting their beautiful kids.

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