Shiloh Jolie-Pitt once had a play date with another celebrity babe

Shiloh Jolie-Pitt’s unconventional lifestyle has made it a little harder for her to make friends beyond her mother, who once described her children to The New York Times as saying, “They’re the best friends I’ve ever had. No one in my life has ever stood by me more.”

While still married and traveling the world with their large 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 kids and our way of life,” Jolie told the Independent in June 2011. “I’d rather they go to a museum and learn to play the guitar and read and choose a book out of love.”

Studying at home and exploring the world with her parents meant Shiloh couldn’t make friends at school like so many other kids do, but it didn’t stop her from meeting and befriending her peers. In fact, her parents once gave her a helping hand by setting her up for a play date with a celebrity baby just a day older than her: Kingston Rossdale.

Shiloh Jolie-Pitt and Kingston Rossdale’s match date sparked tabloid rumour

When No Doubt frontwoman Gwen Stefani briefly flirted with the idea of ​​being an actress, she almost denied Brangelina and her offspring a existence. In 2008, Stefani told Vogue that she auditioned for the role she was playing in the 2005 film Mr. & Mrs. Smith” to Brad Pitt’s bride-to-be. Stefani recalled, “It was between me and Angelina Jolie, and I was like, ‘Oh, great. I got a chance here.’”

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Stefani proved she had no ill will toward the woman who got the role she wanted, and in 2011 helped Jolie set up a playdate for her children, while Us Weekly Stefani and Gavin Rossdale’s eldest son, Kingston Rossdale, hosted for some of Pitt and Jolie’s children – Shiloh, Zahara, Vivienne and Knox – at his family’s home in London. The group ate takeout pasta, per PopSugar, and the kids were photographed rocking face paint.

Kingston and Shiloh were both only 5 years old at the time, but the tabloids wasted no time playing matchmaker; InTouch (via Jezebel) claimed to have inside information that Shiloh had a crush on Kingston. A source said the two tots had a lot in common, including similar taste in movies and a penchant for dressing up.

How Gwen Stefani felt about Shiloh-Jolie Pitt and Kingston Rossdale’s friendship

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 was friends with Kingston Rossdale’s father and mother before he and Angelina Jolie started dating, and becoming parents to children of similar ages strengthened the bond between the longtime friends. Being pregnant at the same time also brought Jolie and Stefani closer. Speaking to The Sydney Morning Herald in 2008, Jolie recalled asking Stefani if ​​she had extra maternity clothes and getting a dress from the singer’s LAMB label as a gift.

However, busy adult lifestyles forced Shiloh and Kingston into a mostly long-distance relationship that required keeping in touch via Skype, reported InTouch (via Jezebel). The only reason the kids were able to get together in London in 2011 was because Pitt was filming “World War Z” there and had brought the rest of the family with PopSugar.

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Stefani once expressed hope for a future where Shiloh and Kingston wouldn’t have to spend so much time apart. “Maybe they’ll marry when they grow up? That would be cute!” she said to Elle.

Shiloh Jolie-Pitt and Kingston Rossdale are friends with other celebrity kids

We’re not sure if Shiloh Jolie-Pitt and Kingston Rossdale remained friends as they got older, but they both seem to enjoy hanging out with other kids who know what it’s like to have famous parents. According to the Daily Mail, Kingston was spotted with Britney Spears’ sons, Sean Preston and Jayden James, outside the Spears home in 2008 and when he celebrated his 4th birthday in 2010, Kingston’s birthday party guests included David and Victoria Beckham’s sons Brooklyn , Romeo and Cruz, via PopSugar.

Shiloh was one of the beneficiaries of her mother’s friendship with fellow “Eternals” co-star Salma Hayek. In a joint interview with Access, Hayek and Angelina Jolie couldn’t say enough nice things about each other. “Salma is so honest and real and a great mom,” Jolie gushed. “And our kids are the same age, so it’s all so much fun; we’re playing date moms.” Per Hola!, Shiloh and her sister Zahara were spotted with Salma Hayek’s daughter Valentina Pinault during a 2021 outing with their moms.

Jolie was also photographed spending time with Grey’s Anatomy star Ellen Pompeo, according to Entertainment Tonight, and an insider told OK! that Shiloh became good friends with Pompeo’s daughter Stella. “It helps [Shiloh] Spending time with people who get it,” the source explained. This explains why Shiloh “Stranger Things” star Millie can count Bobby Brown as one of her famous BFFs.

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