The singer, who once called the actor the love of her life, is alleged to be unaccustomed to that reality, particularly given her own efforts to keep up a youthful appearance over time.
Madonna and Penn were married from 1985 to 1989 after meeting while filming her music video “Material Girl.” Despite their volatile union, the 2 have remained loosely in contact over time.
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The Singer Was Stunned By Sean Penn’s Natural Look
With over 4 many years having passed since Madonna split from ex, Sean Penn, the 2 have each grown older and at the moment are of their sixties.
While Penn’s recent public appearances have shown him embracing natural aging by letting his hair go fully gray and appearing carefree about his increasing wrinkles, Madonna has chosen the trail of rewriting the foundations of beauty and defying time itself with what seem like multiple cosmetic interventions.
Nonetheless, for Madonna, seeing Penn let himself age naturally has come as a shock to her, one she is currently still grappling with
“This just isn’t Sean as she remembers him,” a source said of the singer recently seeing her ex, in response to a report. “She couldn’t imagine it — natural aging, gray hair… It’s just not her Sean.”
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“She’s used to controlling every look, every image,” the insider added. “Seeing Sean age naturally — without filters, fillers, or Hollywood tricks — was a shock to her system. She’s not used to that reality.”
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Madonna Is Concerned About Sean Penn’s Lifestyle After Smoking Incident At The Golden Globes
Penn’s natural aging just isn’t the one thing Madonna appears to be shocked by, as recent reports have revealed that she doesn’t agree along with his lifestyle.
The 65-year-old actor was seen repeatedly smoking throughout the 2026 Golden Globe Awards in Beverly Hills on Sunday, January 11.
Despite being approached on three occasions by event staff and asked to place out his cigarette, he allegedly refused to comply and continued the behavior.
Seeing Penn act in this fashion and remain firmly entrenched in his smoking habits has deeply fearful Madonna.
“It’s brutal to look at what Sean is doing to himself without delay. He appears to be in self-destruct mode,” a source recently told Globe. “He acts like he’s bulletproof, but it surely’s obvious this lifestyle is taking an enormous toll on him.”
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Madonna Was ‘Genuinely in Love’ With Her Ex-Husband Sean Penn
Madonna’s marriage to Penn lasted just 4 years after meeting on the set of “Material Girl” in 1985.
Despite the whole marriage being quite tumultuous, the singer was reportedly “genuinely in love” with the actor while it lasted, in response to Sharon Oreck, who produced the music video.
“She was genuinely in love with him, but it surely felt as if the attraction between the 2 of them was fueled by the general public. He was the budding movie star, she was the budding rock star, and the general public demanded that they arrive together,” the director said in an archival audio featured within the pop goddess documentary “Becoming Madonna.”
“It was like a bomb went off,” Oreck said of the duo’s romance. “America’s bad boy and America’s bad girl.”
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Sean Penn’s Response To The Iconic Singer’s ‘Love Of My Life’ Remark
Madonna appeared to hint that she still has affection for Penn when she was seen referring to him because the love of her life in her documentary.
Nonetheless, it appears the actor feels in another way, as he bluntly responded to the statement during an appearance on Louis Theroux’s podcast in mid-2025, in response to the Each day Mail.
“I remember what she said,” Penn said of the remark when asked by his host if he recalled it from the documentary.
He added, “She’s very sweet. Look, she’s been an excellent friend for plenty of years.”
The Actor Called His Marriage To Madonna A ‘Mistake’
He went on to suggest that their marriage was a mistake despite the whirlwind relationship that they had.
“It didn’t take us long to comprehend that we had mistaken an excellent first date for a marriage partner,” the actor said.
Penn added, “It didn’t take us long to get better after we got divorced, perhaps a 12 months, in a friendship. I even have plenty of fond memories of it – it is not all jail.”
“But there was plenty of alcohol, and she or he’d be fairly accusing me of that,” he further noted about his relationship with Madonna.