Family Album! Reese Witherspoon’s Best Photos With Her Kids Over the Years

Mom first! While Reese Witherspoon has an expansive résumé, she touts parenthood as one of her greatest achievements.

The Legally Blonde star first became a mother in September 1999, welcoming daughter Ava with then-husband Ryan Phillippe. The Cruel Intentions costars — who were married between 1999 and 2006 — later welcomed son Deacon in October 2003.

Despite getting divorced after seven years of marriage, they managed to strike up an amicable coparenting relationship.

“It’s a feeling-out process,” the Shooter alum, who welcomed daughter Kai with ex Alexis Knapp in 2011, told HuffPost Live in 2014. “I think we’ve gotten to a really great place. It’s going well, and she’s happy and remarried, and our kids are incredible. I’m proud of the way we’ve handled it and who our little people are.”

Witherspoon had moved on with talent agent Jim Toth, tying the knot in March 2011. They welcomed their only child together, son Tennessee, one year later. Since becoming a mother of three, the Walk the Line actress has frequently opened up about raising her children.

“You have to have a different relationship with your children [as they mature] … establish a different relationship. It is about honesty. First of all, you know, you’re managing them a lot when they’re little. It is very physical,” Witherspoon said during an October 2022 appearance on the Today show. “And then, it is more emotional support and suggestions — not telling them what to do when they get a little bit older. But you have to really nurture your adult relationships with your children, too, and give them respect and space to become who they are and not who you want them to be.”

While Ava and Deacon have since grown up and left the nest for college, they’ve remained close with their lookalike parents.

“They’re best friends. They just love being together,” a source exclusively told Us Weekly in June 2018 of the Morning Show star and her only daughter’s special bond. “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.”

Witherspoon and the Pennsylvania native ultimately called it quits in March 2023, announcing plans to divorce days before their 12th wedding anniversary.

“We have some personal news to share … It is with a great deal of care and consideration that we have made the difficult decision to divorce,” the Draper James founder and Toth wrote in a joint statement shared via Witherspoon’s Instagram account. “We have enjoyed so many wonderful years together and are moving forward with deep love, kindness and mutual respect for everything we have created together.”

In their social media note, the pair explained that coparenting Tennessee is their “biggest priority” moving forward. “These matters are never easy and are extremely personal,” they added at the time. “We truly appreciate everyone’s respect for our family’s privacy at this time.”

Scroll below to see Witherspoon’s sweetest photos with her children:

Miranda Siwak

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