Ryan Phillippe's 3 Kids: All About Ava, Deacon and Kai

Ryan Phillippe has been a dad since 1999.

The MacGruber star, then 25, welcomed his first child, a daughter named Ava, with then-wife Reese Witherspoon, whom he'd married after meeting at her 21st birthday party. The pair went on to welcome a son, Deacon, in 2003 before eventually splitting three years later. They've continued to make co-parenting a priority since finalizing their divorce in 2008, attending school functions together and sharing family dinners.

Following their breakup, Phillippe spoke to Ellen DeGeneres during a 2010 appearance on her show about maintaining a good relationship with his ex-wife and setting a positive example for their kids.

"It is so important as divorced parents to keep that connection," he said. "It makes the kids feel better that the parents are interacting. We go to all the school events together, and we're there for each other."

In 2011, Phillippe welcomed his third child, daughter Kai, with then-girlfriend Alexis Knapp.

Speaking about Ava and Deacon in PEOPLE's 2021 Sexiest Man Alive issue, he joked, "They're both better looking than me, thankfully." He added, "They obviously have a very pretty mom. Deacon and I connect very heavily in regards to music. He's like my best friend, and Ava is very much my personality."

He also reflected on who they've grown to be, adding, "They're very self-possessed, conscientious people who care about the world, who treat people with respect and take care of themselves. I think that's also something that you model as a parent."

Here's everything to know about Ryan Phillippe's three children: Ava, Deacon and Kai.

Ava Elizabeth Phillippe, 24

Phillippe officially became a dad when he and Witherspoon welcomed their first child together, daughter Ava Elizabeth Phillippe, on Sept. 9, 1999, in Los Angeles.

Ava's name holds special significance for Phillippe, who explained the meaning behind the moniker on The Tonight Show with Jay Leno in 2008.

"My daughter's name is Ava ... [like] Ava Gardner, because to me she was the only woman who could break [Frank] Sinatra," he said, adding that he also had a bulldog at the time named after Sinatra. "So the idea of that name to me is very classy and strong."

Soon after his split from the Sweet Home Alabama actress, Phillippe opened up about how Ava was helping him cope during the "toughest time in my life."

"As difficult as it is, my daughter has been the inspiration," he said during an appearance on The Ellen DeGeneres Show in 2007. "She is beyond, in terms of like conscientiousness and maturity, and she has gotten me through this. I know it sounds pathetic — I'm a 32-year-old guy, but my 7-year-old daughter is getting me through the toughest time in my life, and that's beautiful too."

The following year, he reflected on how "shocking" it was that she was growing up so fast, telling Leno during his appearance on the talk show, "Ava is 8. I can't believe I have an 8-year-old daughter! An amazing, beautiful 8-year-old-daughter. I feel like an 8-year-old myself a lot of the time, so it's shocking to me."

In addition to feeling like a kid, Phillippe is frequently mistaken for one as well — something that doesn't exactly sit well with Ava, he revealed.

"My daughter gets embarrassed sometimes by the fact that I do look so young and I get mistaken for her brother sometimes," he told host James Corden on The Late Late Show in 2016. "Which repulses her! Like, absolutely repulses her that anyone could mistake me for her brother."

Meanwhile, Ava officially entered adulthood when she made her debut into society at the Bal des Debutantes in Paris in November 2017.

In the years since, she's found her own footing in the entertainment industry, pursuing a budding career in modeling and working with brands like Pat McGrath, Beyoncé's Ivy Park and her mom's line, Draper James. She also graduated from UC Berkeley in 2022.

Deacon Reese Phillippe, 20

Phillippe's son, Deacon Reese Phillippe, was born on Oct. 23, 2003, in Los Angeles.

Now 20, the budding musician graduated from high school in spring 2022, which his parents celebrated with a backyard commencement ceremony.

To mark the occasion, the trio posed poolside while decked out in their finest academic garb, with Deacon displaying his diploma and his dad wearing a cap and gown of his own, joking that he "played principal" for the big day.

"Best dad ever," Deacon commented on his dad's photo.

Just a few weeks earlier, Deacon's parents proudly commemorated another of his milestone moments: senior prom. Phillippe shared a photo of himself posing beside Deacon on his Instagram Story, writing, "Sending our sweet meat boi off 2 prom."

The proud dad often shares tributes to his "best friend" on social media, including one photo of the duo sitting side by side, which he captioned, "fthr n sn n bst frnds frvr."

In addition to being best buds, the father-son duo are also workout partners, often hiking in L.A. or hitting the gym together. "We'll do the same workout, and the way he looks after compared to the way I look is really defeating," Phillippe joked to PEOPLE.

Deacon and Phillippe have also bonded over music, having attended the Firefly Music Festival together in 2019. Phillippe reflected on a special moment the pair shared during a road trip to Yellowstone, California, when Travis Scott's album Astroworld first came out.

He explained to PEOPLE, "So our first listen was on this road trip as we're passing the most beautiful, enormous mountains on our way into Yellowstone. And that's something that I won't forget."

Their shared passion for music has impacted Deacon, who has since begun to pursue a career in the industry. In 2020, he released his first hit single, "Long Run."

Speaking to Interview magazine about what initially drew him to music production, he shared that he was influenced by his dad's own knack for making music.

"When I was listening to the radio in the car with my dad, something just clicked. I realized there's more to making music than just being a vocalist, and that a lot of times it's the production that makes me feel something," he explained. "I asked my dad about how it works, and he taught me all the stuff he knew, and then I started watching YouTube videos."

Deacon has also followed in his parent's footsteps in Hollywood, making his acting debut in the third season of Netflix's Never Have I Ever in August 2022.

Kai Knapp, 12

Phillippe welcomed his youngest child, a daughter named Kailani Merizalde Phillippe Knapp, with ex-girlfriend Alexis Knapp on July 1, 2011. Phillippe and the Pitch Perfect actress had briefly dated the year prior.

While Phillippe never publicly addressed Knapp's pregnancy, the actor was in the delivery room when Kai was born. She shares the same middle name as her mother and the last names of both Phillippe and Knapp.

When Kai was less than 3 months old, her mom began filming the hit musical comedy film Pitch Perfect. "No one understood how it was possible to breastfeed a newborn throughout the whole rehearsal and filming 14+ hour days for 3 magical months, but i told them 'you’d be amazed at what you can do, when you have to ... ' " Knapp wrote on Instagram alongside a throwback photo of her and Kai.

Now 12 years old, Kai has joined Knapp at several red carpet events over the years, including the 2019 premiere of Netflix's Green Eggs and Ham and a 2022 release event for Minions: The Rise Of Gru.

In November 2023, Kai spent Thanksgiving with her dad and made her first appearance on the actor's Instagram.

"Had the BEST Thanksgiving wknd w these lil beauties. Sawyer, Ever, Kai & Isla," Phillippe wrote, introducing his followers to his daughter and nieces. "Pizza was had, Elf was watched, Young Sheldon was binged(along w teen romance anime). Boba was had, boardwalk shopping, cooking of pancakes was attempted, and we found some fake snow. + the eagles beat buffalo in OT and moved to 10-1, but I think that only mattered to me."