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Jenna Bush Hager Relates to Madonna's Emotional Confession About Feeling Like an 'Outsider'

Photo of Jenna Bush Hager and Madonna
Source: TODAY With Jenna & Friends/Jay Shetty Podcast/YouTube

On 'TODAY With Jenna & Friends,' Jenna Bush Hager resonated with Madonna's recent admission to not fitting in.

Oct. 2 2025, Published 1:13 p.m. ET

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Jenna Bush Hager is standing by Madonna after her recent vulnerable confession.

During the Thursday, October 2, episode of TODAY With Jenna & Friends, the talk show host, 43, defended the 67-year-old pop star's musings on being an "outsider" her whole life.

Bush Hager played a clip from Madonna's September 29 podcast debut with Jay Shetty, where she made the shocking remarks about her life in private.

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Source: Jay Shetty Podcast/YouTube

Madonna made her first-ever podcast appearance.

"I think I've always felt like an outsider in life. I felt like an outsider growing up in Michigan. I felt like an outsider when I came to New York," the musician revealed. "I felt like an outsider when I moved to L.A. and had my Hollywood life. I always felt like I did when I was in high school. I don't fit in. And not fitting in his what saves you."

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Image of Jenna Bush Hager wants to teach her kids that feeling left out is normal.
Source: TODAY With Jenna & Friends/YouTube

Jenna Bush Hager wants to teach her kids that feeling left out is normal.

Bush Hager thought Madonna made a "really interesting point" and agreed that "if you try to be somebody else for other people, you're never going to please yourself."

"I feel like when we were in high school, it was kind of a simpler time," the media personality expressed. "You probably felt like in places you couldn't fit in, but then you would go sit with your grandma, or you'd go wherever and have a little reprieve from the social impact of whatever. I feel so bummed for the kids of this generation because there's really no safe spot because of social media ... there were definitely moments [before] where you felt like you fit in. I felt like that term is so problematic because you could be yourself. That's the thing."

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Image of Madonna 'always felt like an outsider.'
Source: Jay Shetty Podcast/YouTube

Madonna 'always felt like an outsider.'

Bush Hager — who shares kids Mila, 12, Poppy, 9, and Hal, 6, with Henry Hager — aims to create a safe environment for her family.

"I hope my kids come home and they're like, 'Ah,'" she said. "Of course, there are moments they don't feel like that because mama's strict. But they can come, and they can just exhale. The problem with social media is they're never exhaling."

The host wants to teach her children that feeling left out is "part of life," and they are never alone.

"The more we can be like, 'No, you're never going to feel like you fit perfectly, and that's okay,'" she emphasized. "That's what I feel like Madonna was saying. It's important to hear that from people like her so you're not like, 'Oh, I'm trying to be something for somebody else.'"

Madonna's Spirituality Isolated Her

Image of Jenna Bush Hager applauded Madonna's vulnerability.
Source: Jay Shetty Podcast/YouTube

Jenna Bush Hager applauded Madonna's vulnerability.

During Madonna's two-hour podcast, she also described how her spiritual practice of Kabbalah separated her from her friends.

"Having a spiritual life isn't necessarily going to make you popular. But if you're a conscious person searching for truth, then it's going to be interesting," the "Material Girl" artist said. "Being too comfortable in life is the downfall of a lot of people who started off taking chances, taking risks."

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