One of the most defining magazine covers of the early aughts was rife with plenty of behind-the-scenes turmoil, according to cover girl Mandy Moore.

Moore, 40, appeared on the cover of Vanity Fair’s July 2003 issue alongside actresses including Amanda Bynes, Alexis Bledel, Lindsay Lohan and Evan Rachel Wood with the headline, “It’s Totally Raining Teens!”

Over two decades later, Moore recalled there was “a lot of teenage drama” on the day of the shoot, including “a fight over a boy between two people.”

“I remember feeling like a real outlier and outsider,” the actress said on the Tuesday, April 9, episode of the “Not Alone” podcast. “Like, ‘I am not part of the cool kids club. I don’t know what they’re fighting about.’”

Moore boasted that an awkward interaction with Mary-Kate and Ashley Olsen, who were both featured on the cover, managed to actually stroke her confidence amidst all the chaos.

“One of them had a crush on my boyfriend at the time,” Moore told host Valeria Lipovetsky. “I just remember feeling really cool about that. I was like, ‘Oh, well, I pick ’em good then, I guess! My boyfriend is someone they have a crush on!’ I thought that was pretty hilarious.”

While Moore didn’t name names, she was dating tennis superstar Andy Roddick from 2002 to 2004.

The Vanity Fair cover also featured Moore standing side-by-side with Hilary Duff, which is an experience the two actresses now “laugh about all the time.”

Moore described Duff, 36, as a “very, very dear friend” and noted that even their husbands are “best friends.” Moore married musician Taylor Goldsmith in 2016, while Duff married music producer Matthew Koma in 2019.

“Hilary is just ultimate mom goals in every sense,” Moore gushed. “She is the most incredible mother and businesswoman and she does everything with such grace.”

Duff and Koma share two children — daughters Banks, 5, and Mae, 3 — and in December 2023, they announced they are expecting their third child together. Duff also shares son Luca, 12, with ex-husband Mike Comrie.

Moore, meanwhile, shares sons Gus, 3, and Ozzie, 17 months, with Goldsmith.

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“I’m so grateful and flabbergasted that life brought us back into each other’s orbit in this capacity,” Moore said of her bond with Duff.

The two women are part of a larger community of Los Angeles–area moms who, as Moore explained, constantly help support and boost each other up.

“We’re very much all active in each other’s lives, even though we live in different parts of the city and kids are at different schools and stuff,” she said. “I feel like there’s still that community I can tap into.”

Finding that new tribe has been an illuminating experience for Moore, even though she was warned it’s exactly what she could expect.

“It is funny how some friendships kind of float away and become less of a priority and these new friendships become front and center in your life,” she continued. “People told me that, but again until you’re there you’re like, ‘What, I’m gonna become really close with people just because we have kids or because our kids go to school together?’ It is the case. That’s your community.”

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