Shiloh Jolie-Pitt Once Had A Play Date With Another Celebrity Baby

Shiloh Jolie-Pitt's unconventional lifestyle has made it somewhat more challenging for her to make friends beyond her mom, who once described her kids to The New York Times by saying, "They're the best friends I've ever had. Nobody in my life has ever stood by me more."

When they were still married and globe-trotting with their big brood, Angelina Jolie and Brad Pitt decided homeschooling would be the best option for Shiloh and her five siblings: Maddox, Pax, Zahara, Knox, and Vivienne. "The education system hasn't caught up with our children and our way of life," Jolie explained to the Independent in June 2011. "I'd rather them go to a museum and learn to play guitar and read and pick a book they love."

Learning at home and exploring the world with her parents meant that Shiloh couldn't make friends at school like so many other kids do, but it didn't prevent her from meeting and befriending kids her own age. In fact, her parents once gave her a friendship assist by setting her up on a play date with a celebrity baby who's just one day older than her: Kingston Rossdale.

When No Doubt frontwoman Gwen Stefani briefly flirted with the idea of becoming an actor, she almost prevented the existence of Brangelina and their brood. In 2008, Stefani told Vogue that she auditioned for the role that ultimately went to Brad Pitt's future bride in the 2005 movie "Mr. & Mrs. Smith." Stefani recalled, "It was between me and Angelina Jolie, and I'm like, 'Oh, great. I got a shot here.'"

Proving that she bore no ill will toward the woman who got the role that she wanted, Stefani helped Jolie arrange a playdate for their children in 2011. According to Us Weekly, Stefani and Gavin Rossdale's oldest son, Kingston Rossdale, played host to a few of Pitt and Jolie's kids — Shiloh, Zahara, Vivienne, and Knox — at his family's home in London. The group noshed on takeout noodles, per PopSugar, and the children were photographed rocking face paint.

Kingston and Shiloh were both just 5 years old at the time, but the tabloids didn't waste any time playing matchmaker; InTouch (via Jezebel) claimed to have inside intel that Shiloh was crushing on Kingston. A source dished that the two tots had a lot in common, including a similar taste in movies and a fondness for playing dress-up.

In a 2007 interview with Elle (via Us Weekly), Gwen Stefani revealed that her son and Shiloh Jolie-Pitt went way back. "They were like two little blobs when they met," she said. According to Us Weekly, Brad Pitt had been pals with Kingston Rossdale's dad and mom since before he and Angelina Jolie got together, and becoming parents to children of similar ages strengthened the bond between the longtime friends. Being pregnant at the same time also drew Jolie and Stefani closer together. Speaking to The Sydney Morning Herald in 2008, Jolie recalled asking Stefani if she had any extra maternity wear and being gifted a dress from the singer's L.A.M.B. label.

However, the adults' busy lifestyles forced Shiloh and Kingston to have a mostly long-distance relationship that required keeping in touch via Skype, InTouch (via Jezebel) reported. The only reason the kids were able to meet up in London in 2011 was because Pitt was there filming "World War Z" and had brought the rest of the family with him, per PopSugar.

Stefani once expressed hope for a future where Shiloh and Kingston wouldn't have to spend so much time apart. "Maybe they'll get married when they grow up? That'd be cute!" she told Elle.

We aren't certain whether Shiloh Jolie-Pitt and Kingston Rossdale remained friends as they got older, but they do both seem to enjoy hanging out with other kids who know what its like to have famous parents. According to the Daily Mail, Kingston was spotted hanging out with Britney Spears' sons, Sean Preston and Jayden James, outside Spears' home in 2008, and when he celebrated turning 4 in 2010, Kingston's birthday party guests included David and Victoria Beckham's sons Brooklyn, Romeo, and Cruz, per PopSugar.

As for Shiloh, she was one of the beneficiaries of her mom's friendship with her "Eternals" co-star Salma Hayek. In a joint interview with "Access," Hayek and Angelina Jolie couldn't seem to say enough nice things about each other. "Salma is so honest and authentic and a great mother," Jolie gushed. "And our kids are the same age, so that makes it all so fun; we're play date moms." Per Hola!, Shiloh and her sister Zahara were spotted hanging out with Salma Hayek's daughter, Valentina Pinault, during a 2021 outing with their moms.

Jolie has also been photographed spending time with "Grey's Anatomy" star Ellen Pompeo, per Entertainment Tonight, and an insider told OK! that Shiloh has become good friends with Pompeo's daughter Stella. "It helps [Shiloh] to spend time with people who get it," the source stated. This explains why Shiloh can count "Stranger Things" star Millie Bobby Brown as one of her famous BFFs.