July 5, 2026 10:56 pm EDT

He is the spitting image of his two children with Oscar-winner Reese Witherspoon, but actor Ryan Phillippe’s resemblance to his daughter Ava Phillippe may be the only thing he has in common with the aspiring actress these days.

For the Cruel Intentions actor, 51, has apparently taken a back seat when it comes to his strained relationship with Ava, 26, following his divorce from their mother, the Daily Mail has learned.

As the Legally Blonde actress, 50, forged a ‘really close’ bond with Ava during her formative years, it was her second husband Jim Toth, 55, who insiders say took on the role of ‘dad’ for Phillippe’s children.

Although Witherspoon and Toth subsequently divorced in 2023, sources suggested that the former talent agent ‘had a big hand’ in helping raise Ava and Deacon, 22.

Now, with German financier Oliver Haarmann by Witherspoon’s side at the premiere for her Legally Blonde spin-off series, insiders have shared how the star’s ‘tight-knit’ family has adapted to her new businessman boyfriend.

But between Witherspoon’s blossoming relationship with Haarmann and her amicable co-parenting status with Toth, will Phillippe be pushed even further on the outs?

Pictured in January 2026: Ava Phillippe, 26, is the daughter of actors Reese Witherspoon and Ryan Phillippe

Pictured in May 2025: The actor, 51, has apparently taken a back seat in his allegedly strained relationship with Ava, sources told the Daily Mail

‘Ava was very close with her mom’s ex, Jim,’ one source exclusively told the Daily Mail. 

‘He was around for a lot of the important years she was growing up. He was a really good father figure to her. Jim had a big hand in helping raise Ava.’

After filing for divorce from Phillippe in October 2006, Witherspoon began a relationship with Toth in January 2010 and they were engaged by the end of the year.

Witherspoon made sure to include her children in the wedding ceremony, with then 11-year-old Ava serving as the maid of honor and seven-year-old Deacon being the ring bearer. The nuptials took place in March 2011 on Witherspoon’s ranch in California.

The couple expanded their family in September 2012, when Witherspoon gave birth to her third child, son Tennessee James Toth.

Her mother’s second marriage and the arrival of a new baby came as a welcomed change for Ava, the source explained, as she had witnessed the ‘tense’ relationship between her parents during her early childhood.

‘Things were tense growing up because it took a really long time for Reese and Ryan to get to an amicable place, especially when it came to co-parenting,’ the source said.

‘She’s really close with her mom, so that couldn’t have been easy to see. But that was years ago. Things have gotten much better [between Witherspoon and Phillippe], but their kids are now adults.’

In 2011, Witherspoon remarried to former talent agent Jim Toth. They welcomed son Tennessee James Toth in September 2012 (pictured in January 2020)

Pictured in December 2019: A source described Toth as a ‘really good father figure’ and ‘had a big hand’ in raising Witherspoon’s children Ava and Deacon

Ava was born in September 1999, just three months after Witherspoon and Phillippe were married. The actress was just 23 years old when she became a first-time mom, while her husband was 24.

In the years since, Phillippe has gushed over his eldest daughter in interviews and on social media, claiming the day Ava was born was the day he ‘learned what love truly is.’

In 2014, he described how he had raced by helicopter from Utah, where he was shooting thriller The Way Of The Gun, to Beverly Hills for her birth.

‘With my stomach in knots, exhausted & dirty, covered in syrupy fake blood & shards of candy glass the heli[copter] found the pad and I was taken to an area to sterilize myself,’ he posted on X.

‘I made it to my then wife’s bedside w/ two hours to spare before my baby girl first entered the world. Fifteen years ago I learned what love truly is.’

However, Witherspoon has told a different story, suggesting she felt abandoned by Phillippe during those early months.

‘I did not have a lot of support with my first baby and I learned really early, like, this is not going to work,’ the actress told the We Are Supported By podcast in 2021.

‘I tried to muscle through for five months with Ava, just not sleeping and I became delirious. I was lucky enough to have money saved and I didn’t have to work, but it’s just not a one-person job. I would even say it’s not a two-person job.’

Pictured in August 1998: Witherspoon and Phillippe were married in June 1999 and welcomed daughter Ava three months later. They announced their separation in October 2006

Phillippe described the day his daughter Ava was born as when he ‘learned what love truly is’

The Cruel Intentions co-stars welcomed their second child, son Deacon, in 2003 but announced they were separating three years later.

Phillippe went on to describe their divorce as the ‘toughest time in my life,’ but credited Ava with getting him through it.

‘As difficult as it is, my daughter has been the inspiration,’ he said on The Ellen DeGeneres Show in 2007.

‘She is beyond, in terms of conscientiousness and maturity, and she has gotten me through this. I know it sounds pathetic – I’m a 32-year-old guy, but my seven-year-old daughter is getting me through the toughest time in my life, and that’s beautiful too.’

However, it seemed that their close father-daughter bond had taken a turn at some point during Ava’s teen years, according to Phillippe’s Instagram activity. 

While the actor has made sure to celebrate his daughter’s birthday each September with a tribute posted to Instagram, his social media posts featuring Ava began to dwindle after her 19th birthday.

It was around that same time that Phillippe’s ex-girlfriend, former Playboy model Elsie Hewitt, accused Phillippe of assault in a $1 million lawsuit in 2018.

In the legal filing, Hewitt – who now shares a seven-month-old daughter with comedian Pete Davidson – accused Phillippe of throwing her down the stairs in her Los Angeles home, before ‘kicking and striking’ her.

Pictured in 2022: Phillippe was previously accused of assault by ex-girlfriend Elsie Hewitt in a $1 million lawsuit filed in 2018. He denied the allegations and they settled out of court in 2019 for an undisclosed amount

Pictured in April 2024: Source described Ava’s relationship with Witherspoon as ‘tight knit’ and ‘really close’

She also claimed in the legal filing that he used drugs, alcohol and steroids, which caused mood swings and extreme anger. In 2023, Phillippe announced on Instagram that he was sober.

Phillippe denied Hewitt’s allegations and emphasized his support for ‘women’s rights, feminism and advocacy.’ The lawsuit was settled out of court for an undisclosed amount in 2019, just days before they were set to go to trial.

Despite Phillippe denying the allegations, the Daily Mail previously reported that the lawsuit had driven a wedge between the actor and his daughter, who is an outspoken advocate on issues like body positivity, mental health awareness and LGBTQ+ rights.

Instead, her brother Deacon continued to make appearances on his dad’s social media page, including snaps from his high school graduation in 2022 and photos from Deacon’s album release party in 2023.

‘Ryan is super close to Deacon. They do a lot of things together as a father and son, so much so that Ryan is more of a best friend,’ a source told the Daily Mail.

‘Deacon hangs out with his father more than his mom because they go unrecognized, whereas when he’s with his mom, they’re always seen in the public and paps are taking photos. He can live somewhat of a more normal life with his father.’

It wasn’t until May this year, when Deacon graduated from New York University, that Phillippe decided to post a photo of his daughter and son from the ceremony. 

However, Ava noticeably doesn’t follow her dad on the platform.

A source said Phillippe and his daughter Ava ‘put on a united front to support Deacon’ at his graduation from New York University last May

The insider shared that Phillippe has ‘made an effort’ to work on his relationship with his daughter, but it will take some time to ‘repair’ their once-close bond.

‘Ryan wants to repair his relationship with Ava. He’s made an effort to be apart of her life but it’s not being reciprocated,’ the source said. ‘He would never want to not be apart of her life. It’s a sad situation. Their relationship is not what it used to be.’

Although the source acknowledged how Phillippe and Ava ‘put on a united front to support Deacon’ at his college graduation, they maintained that Ava’s ‘mind has been made up and it seems like it’s just going to take time to repair.’ 

Although her relationship with Phillippe has had its ups and downs, that hasn’t stopped Ava from following in her father’s footsteps. 

She has made appearances in music videos for singers Role Model and Ella Langley, and landed one-episode stints on the TV series Doctor Odyssey and Ransom Canyon.

Ava is expected to make her feature film debut in the upcoming movie Laura Dean Keeps Breaking Up with Me, adapted from the young adult graphic novel by Mariko Tamaki.

She recently starred in a social media campaign for the new Vince Camuto fragrance, Wonderbloom Bliss, and launched a limited-edition clothing collection for Bloomingdale’s in-house brand Aqua last year.

In addition to her two siblings, Ava was raised in Los Angeles and graduated from high school in 2018. She went on to attend the University of California, Berkeley, where she studied social welfare, and graduated in 2022.

Pictured in February 2026: Ava is following in her parents’ footsteps, having appeared in the TV shows Doctor Odyssey and Ransom Canyon. She is expected make her film debut in the upcoming movie Laura Dean Keeps Breaking Up with Me

Although she continues to spend time in Los Angeles thanks to her burgeoning acting and modeling career, a separate source shared how Ava has come to appreciate her life outside of the spotlight and away from Hollywood.

‘Ava has spent many years in the Nashville event and party scene on the down low. She loves it out there, just like her mom, and seems to prefer it to the Hollywood lifestyle,’ the second insider told the Daily Mail.

Following her divorce from Toth in 2023, Witherspoon reportedly relocated from Los Angeles to her hometown of Nashville, Tennessee, where she owns a 15,000-square-foot estate worth $18 million and lives full-time.

It is understood that Witherspoon rarely spends any time in Los Angeles these days, as she ‘hates the Hollywood life,’ and only finds herself traveling to the city for work.

Luckily for Witherspoon, it appears that her new romantic partner happens to agree with having a slower-paced lifestyle.

Witherspoon has been romantically linked to Haarmann, a German financier, since July 2024. While it is unclear how the pair met, they have been spotted packing on the PDA during romantic getaways to France and date nights in New York City.

The divorced father of two boasts an impressive resume, having attended Brown University and Harvard Business School. He was a former partner at a global investment firm in London, before becoming a founding partner at his own private equity firm, Searchlight Capital Partners.

The businessman, who is also a minority co-owner of NHL’s New York Islanders, has a jaw-dropping net worth estimated around $440 million.

Witherspoon made her first official appearance with boyfriend Oliver Haarmaan at the New York City premiere for Prime Video’s Elle series in June (seen)

Pictured April 2026: Witherspoon has been romantically linked to Haarmaan since July 2024 following her divorce from her second husband in 2023

In May, Witherspoon and Haarmann made their first official appearance as a couple at the New York City premiere of Prime Video’s Legally Blonde prequel series, Elle. Witherspoon, who is an executive producer for the series, also walked the red carpet with her son Deacon.

Her relationship with the private, successful businessman appears to be a perfect match for the equally ambitious Witherspoon, who transitioned her own career from Oscar-winning actress to executive producer and founder with an estimated $400 million fortune.

It is also a plus that Haarmann has no ties to Hollywood unlike her previous husbands, who were both involved in the entertainment industry.

A third source said about her businessman boyfriend, ‘She likes that he’s just a normal guy. She hates the Hollywood life.’

The pair have seemingly found a healthy balance, with Haarmann ‘visiting [Witherspoon] on set’ and the actress ‘spending time with him in New York,’ as they’ve been frequently photographed grabbing dinner at celebrity hotspots like Cafe Cluny and L’Artusi.

Witherspoon has even introduced her boyfriend to her close friends and fiercely ‘protective’ children, sources say.

‘Oliver seems to get along with everyone in Reese’s inner circle including her kids,’ the third insider said. ‘They are very protective of their mom and extremely close with her. They are a tight-knit family and really nice kids.’

Indeed, the blended family’s bond was on full display at Deacon’s graduation from NYU last May, where both of Witherspoon’s ex-husbands were also in attendance.

Outside the ceremony, Witherspoon and Phillippe were seen smiling and snapping photos of their son in his purple graduation robes. The exes posed for photos with Deacon, as well as his siblings Ava and Tennessee.

At one point, even Phillippe and Toth appeared to be chatting amongst the crowd of proud family members, though Haarmann was not in attendance.

The Daily Mail has contacted representatives for Witherspoon and Phillippe for comment. 

Read the full article here

Share.
Leave A Reply

Exit mobile version